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A Handbook of

Spectroscopic Data

CHEMISTRY
(UV, JR, PMR, JJCNMR and Mass Spectroscopy)

B.D. Mistry
B.K.M. Science College.
Va/sad - (Gujarat)

Oxford Book Company


Jaipur, India

ISBN: 978-81-89473-86-0
Edition 2009

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Contents

1.

Ultraviolet Spectroscopy

2. Infrared Spectroscopy
3. Proton Magnetic Resonance Spectroscopy
4. Be NMR Spectroscopy
5.

Mass Spectrometry

6.

Structural Data Obtainable from Different Spectra

Index

1
26
64
99
128
237
240

"This page is Intentionally Left Blank"

Ultraviolet Spectroscopy

1.1

Calculating Absorption Maxima of Unsaturated Compounds


Dienes and trienes : If the compound is suspected to be a conjugated

or substituted diene, its wavelength of maximum absorption can be predicted


with the help of Table I. I. To be able to use this table, one must first learn to
recognize different types of dienes, conjugations, double bonds, etc. These
are as follows:

c=c< _ ) C=C< A linear conjugation; for example, 1,3,5


C-C
hexatriene, isoprene,etc.
) C=C<
A cross conjugation.
ii) )C=C
)C=C<
i) )

iii)

iv)

o
o

A cyclic diene; for example, cyclohexadiene,

cyclohepta 1,3- diene, etc.


A semicyclic diene; one of the double bonds
forms part of a ring and the other is
exocyclic, or outside the ring. When only
one of of the two Sp2 hybridized carbons of
a double bond is a part of the ring under

Spectroscopic Data Chemistry


consideration, such a double bond is called
an exocycIic double bond.
A homoannular diene is one in which the

v)

two double bonds are conjugated and are in


a single ring.
Note that both double bonds are
exocycIic to ring B.
vi)

A heteroannular diene is a conjugated system


in which the two double bonds belong to two
different rings. However, these double bonds
are also exocycIic, one of them being exoto ring A and the other exo-to ring B.

Table 1.1: Woodward's and Fieser's rules for Diene absorption (ethanol
solution)
i)

Base value for an unsubstituted, conjugated, acyclic or


heteroannular diene

ii)

214 nm

Base value for an unsubstituted, conjugated


homoannular diene

253 nm

Increments for
iii) Extra double bonds in conjugation (for each C=C)

+30 nm

iv) ExocycIic double bond (effect is two fold ifbond is


exocylic to two rings)
v)

+5nm

Substitutents on Sp2 hybridised carbon atom, per substituent


a) O-acyl (-O-CO-R or -O-CO-Ar)

Onm

b) Simple alkyl (-R) or ring residue

+5nm

c) Halogen (-CI, -Br)

+5nm

d) O-alkyl (-OR)

+6nm

e) S-alkyl (-SR)

+30nm

f) N-alkyl, (-NRR ')

+ 60 nm

vi) Solvent correction

Onm

Ultraviolet Spectroscopy
,

The following points are to be noted:

The cyclic homoannular base values refer to a six membered ring


only. For other rings the values are:
Five membered ring (C s)

228 nm

Seven membered ring (C 7 )

241 nm

Accuracy of prediction is 5 nm

If there is more than one possibility for calculating Amax, the highest
Amax value usually agrees with the observed value.

Limitations

Agreement is quite good for acyclic and six-membered ring polyenes


but not so for other rings in some cases.

Steric strain can also affect the position (Amax) of the band,
sometimes very greatly if the strain is high. A simple example of
this is 1,2 dimethylene cyclohexane, which gives a strong UV band
at Amax 220 nm (E 10,050) which is quite different from the
calcualted value.

Polyenes : The above rules (Table 1.1) holds fairly well for unsaturated
compounds containing up to four conjugated double bonds. However, for
systems of extended conjugation, such as those found in carotenoid pigments,
Fieser and Kuhn have suggested equations to calculate the basic Amax and
Em.. ofUV absorption.
Amax (in hexane) = 114 + 5M + n (48.0 - 1.7n) -I 6. 5Rendo - IOR exo
E ma , (in hexane)

1.74 x 104n

Where
n = number of conjugated double bonds
M = number of alkyl or alkyl like substituents on the conjugated system.
Rendo = number of rings with endocyclic double bonds in the conjugated system.
Rexo =

1.2

number of rings with exocyclic double bonds.


Calculating Absorption Maxima of Carbonyl Compounds
The basic chromophore containing a >C=C< (--ene) conjugated with a

>c=o (-one), as in

Spectroscopic Data Chemistry


P

> C = C- C = 0

.
IS

called an enone. If a carbonyl group is conjugated

with two double bonds (-cliene), such as


Ii
y
P a
>C=C-C = C-C = 0
The compound is known as a dienone. In the case of cyclic compounds,
the ethylenic double bonds conjugated with the carbonyl may be homoannular
or heteroannular.

Table 1.2: Rules of Enone and Dienone absorption

P-

paZ

paZ

C = C - C = 0 and 0 - C = C - C = C - C = 0
Enone
Dienone
Z = C, enone, Z = H, aldehyde
Z = OH, acid, Z = OR, ester

Parent enone (acyclic or rings larger than 5 members)


5-membered cyclic enone
Aldehydes
Acid and Esters
Increments for Double bond extending conjugation (for eacb one)
Homodiene component
Exocyclic double bond (or any >C=C< endocyclic to 5- or 7member ring in a case of acid and ester)
Alkyl group, ring residue
a

215nm
205nm
210nm
195nm
+30nm
+39nm
+5nm
+IOnm
+12nm

y
Hydroxyl (-OH)

Alkoxyl (-OCH 3)

and higher

+ISnm

+35nm

+30nm

y
a
y

50nm
+35nm
+30nm
+ 17nm

31nm

Ultraviolet Spectroscopy
Acetoxyl (-O-COCH 3 )
Dialkyl aniino (-NR)
Chlorine (-CI)

a, ~ or <')

~
a

+ 15nm
+12nm

+ 85nm
+ 25nm

Thioalkyl (-SR)
Bromine (-Br)

6nm

+ 95nm

~
Solvent correction (see table below)

+30nm
variable

Solvent Corrections (Enones)


Solvent
Ethanol
Methanol
Water
Chloroform
Dioxane
Ether
Hexane
Cyclohexane

Correction

o
o
-8 nm
+ I nm
+5 nm
+7nm

+ 11 nm
+ II run

Accuracy of prediction 5 nm.


1.3

Calculating Absorption Maxima of Aromatic Molecules

There are two types of aromatic molecules: benzenoid and


nonbenzenoid. Their spectra show considerable resemblance. In fact, the
presence or absence of certain features in UV spectra, such as a low intensity
band (known as a fine structure band) at or about 255 run, is often used to
detect the aromatic character of an unknown substance.
Benzene Chromophore
The simplest aromatic compound is benzene. It has a ring current of 1t
electrons, which shows strong 1t ~ 1t* absorptions at 184 run (Em" 60,000),
and at 204 nm (Emax 7900). (This is called a primary band.) Benzene exhibits
a low intensity band at 256 nm (Emax 200) (Known as a secondary or finestructure band), with a series offine-structue bands between 230 and 270 nm).
Any substitution ~ the benzene ring, irrespective of its electronic character

Spectroscopic Data Chemistry

(electron-donating or electron-withdrawing character) shift the primary band

(204 nm) to longer wave lengths. With polar substituents, e.g.


etc. which allow for the n

~ 1t

-N~,

-OH,

conjugation and -C = 0 and -N0 2 where

polarisability is of importance, absorption due to electron transfer transitions


is apparent. These two types of transfer can be expressed as shown below:

Chromophore substitutents:

Auxochrome substituents:

Table 1.3: Scotts rules for calculation ofAmax ofthe ET (electron transfer)
band of aromatic carbonyl compounds
Ar-C-Z

II

o
Parent chromophore : Ar=C6HS
Z = Alkyl or ring residue, (e.g.; ArCOR) 246 run
250 run
Z = H, (Ar CHO)
Z = OH, OAlk, (ArCOOH and ArCOOR) 230 run
Increment for each substitutent on Ar:
- Alkyl or ring residue
0-, m+3 nm
p+ 10 nm
- OH, -OAlk
+7 run
0-, m+25 run
p-- 0- (oxyanion)
+Ilnm
o+20 run
m+ 78 run"
p-

In heterocyclic chemistry
model compounds are
essential for the interpretation of most spectra.
No rules are available for
the predicition ofthe wavelength maxima ofaromatic
compounds except in the
case of aromatic carbonyl
compounds where acetophenone is taken as the
parent chromophore, and
increments allotted on the
usual basis (Table 1.3)

Ultraviolet Spectroscopy

--

CI

0--,

m-

+0 mn

p-

+ 10 nm

Br

0--,

m-

NH2
NHCOCH 3

2 nm

p-

+ 15 nm

o-,m-

+I3nm

p-

+ 58 nm

o-,m-

+20nm
+45nm

NHCH 3

pp-

N(CH 3)2

o-,m-

+20nm

p-

+ 85 nm

+ 73 nm

"This value may be decreased markedly by steric hindrance to coplanarity.


Let us now apply the rules in Table 1.1, 1.2, and 1.3 to a few known
compounds and compare the resulting values of Amax with the values observed
experimentally.
I. Dienes
(1) Abietic acid

Basic heteroannular diene

214nm

Exocyclic double bonds (1 x 5)

05nm

Substituents R (4

20nm

5)

Calculated Amax

239nm

Observed

241 nm

[Chromophore is shown by heavy lines; numbers indicate substituents.]

Spectroscopic Data Chemistry

8
(2) Ergosterol

HO
253 nm

Basic homoannular diene


Exocyclic double bonds (2 x 5)

lOnm

Substituents R (4 x 5)

20nm

Calculated "'-max

283 nm

Observed

282 nm

3.3, j3-Acetoxyergosta-5,7,14,22-tetraene
4

In compounds containing both


homoannular and heteroannular double
bonds, the diene system which requires
least energy for excitation (i.e. the one
with the longer wavelength of absorption)
is used as a base.
253 nm
15 nm
25nm
30nm

Basic homoannular diene


Exocyclic double bonds (3 x 5)
Substituents R (5 x 5)
Extra double bond in conjugation

323 nm
319nm

Calculated "'-max
Observed
II. Polyenes
(1) All trans j3-carotene

Me

Me
Me
Me

Me

Ultraviolet Spectroscopy

Basic Amax value

114 nm

= number of alkyl substituents, 5 x 10 add

50 nm

n = number of conjugated double bonds,

11

[48-(1.7

11)]

add

322.3 nm

Rendo = number of rings with endocyclic double bonds,


2 x 16.5, substract
Rexo

= number of rings with exocyclic double bonds,

ox

Emax

33.0 nm

10, substract

00.0 nm

Calculated Amax

453.30 nm

Observed

452.00 nm

1.74 x 11 x 104

= I 9.1 x 104 (calculated)


=

15.2 x 10 4 (observed*)

The equation for calculating

Emax

is semi-empirical, the value calculated

does not always correspond well with the observed value.


(2) All trans Iycopene

114 nm

Basic Amax

M=5 x 8

add

40nm

n= 11 x 148-(1.7 xII)

add

322.3 nm

(Note: Double bonds at ends are not in conjugation with others)

max

= 1.74

substract

00.0 nm

substract

00.0 nm

Calculated Amax

476.30 nm

Observed

474.00 nm

x II x 104

= 19.1 x 104 (calculated)

= 18.6

x 104 (observed)

10

Spectroscopic Data Chemistry

III. Enones
(1) Cholest--4-en-3-0ne

Parent base
Subst::iJ:uents~, ~

(2 x 12) add
Exocyclic = C< add

215 nm
24 nm
05nm

Calculated AEtOH
max

244nm

Observed

241 nm

(2) Cholesta-2,4-dien-()....{)ne

Parent base
Extended conjugation
Homoannular component
Substituents a. (l x 10)
8 (l x 18)

(3) 3,

215 nm
add
add
add
add

30nm
39nm

10 nm
18 nm

Calculated AEtOH
max

312 nm

Observed

314 nm

~-Acetoxy-7-()xolanosta-5,18,11-triene

11

Ultraviolet Spectroscopy

215 nm

Parent base
Extended conjugation

add

30 nm

Homoannular component

add

39 nm

Exocyclic double bond

add

5nm

Substituents a(l)( 10)

add

10nm

12)

add

12 nm

0(\ x 18)

add

18 nm

~ (\ x

Calculated A. EtOH
max

329 nm

Observed

327 nm

(4) Cycloheptene-l--carboxylic acid


a

II

ot~H
IK. p
Parent base
Substituents a(l x lO)

add

IOnm

~(lxI2)

add

12 om

add

05 nm

C=C endocyclic to 7-member ring,


Calculated A. EtOH
max

195 nm

222 nm

(5) 3-MethyI-2-butenoic acid


CH 3

CH 3-C = C-COOH

Parent base

195 nm

Substituents a (l x 10)
~(l x

10 nm

12)

12 nm

Calculated

217 nm

Observed value

216 nm

12

Spectroscopic Data Chemistry

Dicarbonyl compounds

Diosphenol
215 run

Parent base
2~

Substituents

(2 x 12)

24 run

a-OH (1 x 35)
Calculated

35 run

AEtOH
max

274 run

Observed AEtOH
max

270nm

In cyclic a-diketones, the enolic form is generally more stable than the
keto foml and therefore, the absorption is related to that of an a, 13-unsaturated
carbonyl system. Six-membered cyclic a-diketone known generally as
diosphenols, exist in solution largely in the enolised form. In strong alkaline
solution the absorption shifts to about 50 nm to longer waves, due to the
formation of the enolate ion, to enable diosphenol structures to be characterised.
Acetyl acetone exists in the enolic form to the extent of about 90% in
solution in non-polar solvents and the absorption directly depends on the
concentration of the enol tautomer.

..' H ""

II

II

II

CH -C
J

<

CCH

'"

a~-diketone

Isoo ctane 272

274,

C.CH.

-'"

CH

Acetyl acetone

>CH.--C

CH 2

"'rna,,;

Ema~ 12,000
E

max

2050

-f"

'

Ultraviolet Spectroscopy

13

However, in the case of acetyl acetone agreement with the calculated


wavelength (257 nm) is indifferent. This may be due to the fact that the strong
internal hydrogen bond forces the carbonyl group and the double bond into a
configuration different from that which is present in cyclic structures, e.g.,
diosphenol exists almost entirely in the enolic form.
1,3-cyclohexanedione, absorbs at 253 nm

(Emax

22,000) in ethanol

O~OH

O~O

V<-->~ -V
1,3-Cyclohexanedione

The formation of enolate ion in alkaline solution in these cases also


shifts the strong absorption band. Quinones represent a-, or vinylogous adiketones. The spectrum of p-benzoquinone is thus found to be similar with
that of a typical a, f)-unsaturated ketone with the strong K-band appearing at
242 nrn and a weak R-band near 434 nm.
A.~:ne = 242 nrn (E 24,000)

(7t ~ 7t*

K-band)

281 nrn (E 400)} n ~ 7t *


434 run (E 20) R - band

The colour of the simpler members is due to the weak n ~ 7t* transition
which is also present in a-diketones. The n ~ 7t* transitions of a-diketones in
the diketo form gives rise to two bands one in the usual region near 290 nm
(E

30) and a second (E 10 ~ 30) which stretches into the visible 340--440 nm

region to give yellow colour to some of these compounds.

IV. Aromatic carbonyl compounds

o
II

1.

I -. . . :

HO"'-.cr

/
HO

Base value
"-. CH

246nm

OHinm

07 nm

OH inp

25 nm

278 nrn

14

Spectroscopic Data Chemistry

2.

Base value

00

(CH,),NO
H,NO

Brin m
-CH 2 in 0

246nm
02nm
03 nm
251 nm

Br

3.

4.

I~

Base value

250nm

NMe 2 inp

85nm
335 nm

CHO
Base value

230nm

NH2 in p

58nm
288nm

COOH

Another approach to predicting, the "-max of the primary band of


substituted benzenes involves the use ofTable 1.5. This table has been successfully
used with disubstituted compounds when the following rules are used:
I. Para substitution:

a.

b.

Both groups are either electron donating or electron withdrawing:


Only the effect of the group causing the larger shift is used. For
example, the "-max ofp-nitrobenzoic acid would be expected to be
the same as that of nitrobenzene, -(203.5 + 65.0) = -268.5 (in
alcohol solvent).
One group is electron donating and the other electron withdrawing:
The shift in the primary band of such a disubstituted benzene is
usually greater than the sum ofthe shifts caused individually by the
two groups. Such large shifts in p-disubstituted benzens are
attributed to interaction resonance, as illustrated below:

15

Ultraviolet Spectroscopy

2. Ortho and Meta substitution: The shift effects are additive.


Table 1.4: Absorption characteristics of some polycyclic aromatic
compounds
Compound

Amax,

emax

nm

Amax, emax

nm

Amax, emax

nm

CD

184

47,000

203

7,400

255

230

ro

220

1,10,000

275

5,600

314

316

OGCJ

252

2,00,000

375

7,900

252

50,000

295

13,000

330

250

240

89,000

334

50,000

352

6(30

268

1,41,000

320

13,000

360

630

278

1,30,000

473

11,000

580

12,600

Benzene
:::-..

/-

Napthalene
:::-..
//Anthracene

~
I"
/-

Phenanthrene

m
~ I/-

Pyrene

Chrysene

OXO
:::-..

/-/-/-

Napthacene

:::-..
~
/-/-/-/-

Pentacene

These weak bands are usually submerged by strong adjacent bands .

16

Spectroscopic Data Chemistry


~

Table 1.5: Calculation of the Primary Band (1[


substituted Benzenes (CH 30H solvent)
Base Value: 203. 5 nm

1[*Transition) of

Substitutent

Shift

Substituent

Shift

-C H3
-CN
-CHO
-COCH3
-COOH
-Br
-CI

3.0
20.5
46.0
42.0
25.5
6.5
6.0

-NH2
-NHCOCK
-N02

26.5
38.5
65.0
7.0
31.5
13.5

-OH
-0-OCH 3

Absorption Characteristics of Disubstituted Benzens:


1[
Compound

o-N0 2 Phenol
m-N0 2 Phenol
p-N0 2 Phenol
o-N0 2 Aniline
m-N0 2 Aniline
p-NO? Aniline

1[*

Transition
KBand
Amax (nm)
Emax
279
6,600
274
6,000
318
10,000
283
5,400
280
4,800
381
13,500

BBand
Amax (nm)
Emax
3,200
351
333
1.960
Submerged
412
4,500
358
1,450
Submerged

Table 1.6: Absorption characteristics of Aromatic systems and their


substituted derivatives
Compound

Solvent

Primary band
1[ ~ 1[*
Transition
KBand

Amax

rna,

(nm)
Benzene
Toluene
o-Xylene

Hexane
204
Methanol(2%) 206.5
Methanol
210

1[

Secondary band
1[*
n ~ 1[*

Transition
BBand

Transition
RBand

Amax

Amax

max

(nm)
7,900
7,000
8,300

256
261
263

(nm)
200
225
300

E max

17

Ultraviolet Spectroscopy
Compound

Solvent

Primary band
1t ~ 1t*

Transition
KBand
Amax

Emax

(nm)

Secondary band
n ~ 1t*
Transition
Transition
RBand
BBand
1t .~ 1[*

Emax

max

max

Emax

(nm)

(nm)

m-Xylene

Methanol

212

7,200

265

300

p-Xylene

Methanol

212

8,000

274

460

244

15,000

280

1500

328

20

Acetophenone Ethanol

240

13,000

278

1,100

319

50

Benzophenone Ethanol

252

20,000

325

180

Nitrobenzene

Hexane

252

10,000

280

1,000

330

125

Benzonitrile

Water

224

13,000

271

1,000

Alcohol

232

14,000

262 2,400

sylfone

Alcohol

217

6,700

Biphenyl

Alcohol

246

20,000

Benzaidehyde Ethanol

Diphenyl
Sulfoxide
Methyl phenyl

2,2'-Dimethyl

264

977
Submerged

222

270

800

methane
Ethanol
Styrene
Hexane
Phenylacetylene

500

244
236

12,000
12,500

262
282
278

Stilbene (cis)

Alcohol

283

12,300

Submerged

Stilbene (trans) Alcohol

295

25,000

Submerged

Cinnamic acid (cis)

268

10,700

(trans)

272

15,900

biphenyl
Diphenyl-

1-Pheny I-I ,3butadiene (cis) Isooctane

268

18,500

(trans) Isooctane
1,3-Pentadiene

280

27,000

223
223.5

22,600

(cis) Alcohol
(trans) Alcohol

23,000

450
650

18

Spectroscopic Data Chemistry

Compound

Solvent

Primary band

n*

Transition
KBand
Amax
E
max
(nm)

Secondary band
n*
n ~ n*
Transition
Transition
BBand
RBand
Amax E m.. Amax E rna<
(nm)
(nm)

Chlorobenzene Ethanol

210

7,600

265

240

Thiophenol

236

10,000

269

Methanol (2%) 217


Anisole
210.5
Phenol
Water
Phenolate anion Alkali (aq)
235
Water (P H3)
214
o-Catechol
o-Catecho late Water (PHIl) 236.5

6,400
6,200

269
270

700
1,480

Hexane

9,400
6,300

1,450
287 2,600
276 2,300

6,800

292 3,500

8,600
7,500

280

1,430

254

160

anion
Aniline
Water
AniliniumcationAcid (aq)
Acetanilide
Water

230
203
238

Diphenyl ether Cyclohexane

255
275
375
474

Naphthalene
Anthracene
Tetracene
(Napthacene)
Pentacene
Pyridine

Ethanol
Hexane

Quinoline

Cyclohexane

lsoquinoline

Cyclohexane
Ethanol

Acridine

Ethanol
Ethanol
Ethanol

580
257
270
265

10,500
11,000

272 2,000

5,700
8,000
13,000

312

250

270

450

15,000
2,750
3,161

358

4,170
10,000
Band I
10,000

Furan

Cyclohexane

200

Pyrrole
Thiophene
Pyrazole

Hexane
Hexane
Ethanol

209
231
214

315 2,500
313

1,800
Band II

252

I"

6,730 240
7,100 269.5

300"
1.5"

3,160

These weak bands may be due to impurities rather than a forbidden


transition (n

n*) ofa hetero aromatic molecule.

19

Ultraviolet Spectroscopy

Spectra of nonbenzenoid aromatic hydrocarbons show considerable


resemblance to spectra ofbenzenoid compounds, Tropolone and its derivatives
show absorption in the region 220 - 250 nm (

Emax

ca 30,000) and 340 - 375

nm (Emax ca 8,000); the latter absorption is characterized by the group of fine


structure bands typical of aromatic systems.

Q
HO

tropolone

Azulene and its derivatives have complicated spectra consisting of a


number of relatively intense bands throughout most of the ultraviolet region
(up to 360 nm) and a number of relatively weak bands throughout most ofthe
visible region (500 - 700 nm). As a consequence of the latter, azulene and
most of its derivatives are blue.

azulene

1.4: Approximate lower cutoff wavelengths* for commonly used solvents


in UV-visible spectroscopy of organic substances
Solvent

Cutoff

Solvent

wavelength, nm

Cutoff
wavelength, nm

200-250

250-300

Acetonitrile

2\0

Benzene

280

n-Butanol

210

Carbon tetrachloride

265

Chloroform

245

N,N-Dimethylformamide

270

Cyclohexane

210

Methyl formate

260

Decahydronapthalene

200

Tetrach loroethy lene

290

1, I-Dichloroethane

235

Xylene

295

Dich loromethane

235

20

Spectroscopic Data Chemistry

Solvent

Cutoff

Solvent

wavelength, nm
Dioxane

225

Dodecane

200

Ethanol

210

Ethyl ether
Heptane

300-350
Acetone

330

210

Benzonitrile

300

210

Bromofon-n

335

Pyridine

305

Hexane

210

Methanol

215

Methylcyclohexane

210

isooctane

210

isopropanol

215

Water

210

Cutoff
wavelength, nm

350-400

Nitromethane

380

Cutoff wavelengths: i.e. useful wavelength range is beyond the indicated


wavelength.

Exercises and problems:


(1) Explain the differences in the electron spectra of compounds (2) and
(3) compared to compound (1)
I.

(CH 3)2 N-Q-N = N-Q-N0 2


"-max = 475, E = 32,000

2.

= N~
~ NO
(CH.)
, 2N-~N
)=/
2
CH 3
"-max = 438, E = 22,000

....

.).

(CH 3)2 N-p-N = N-o-N0 2


HC(CH 3)2
"-max = 420, E = 18,600

(2) Identify which one of the following two isomers has the electronic
absorption band with "-max = 241 nm and Emax = 18000

21

Ultraviolet Spectroscopy

(1)

(3) Which structural features may produce a bathochromic or a hypsochromic effect in an organic compound.
(4) Aniline absorbs at 230 nm (E8600), however, in acid solution the main
absorption band is seen at 203 nm (E7500) and is comparable with
benzene. Explain.

(5) o-Nitrophenol gives a UV band at t..max 350 nm when the spectrum is


recorded in 0.1 N HCl solution, but the band is observed at t..max 415
nm in 0.1 N NaOH solution. Explain.
(6) Optical whiteners are used to make white clothes appear brighter. Can
you suggest an explanation for the brightening action?
(7) Explain the substitution pattern on the following enone and calculate
the position ofK band.

(8) The position of absorption of acetone shifts in different solvents: 279


nm (hexane); 272 nm (ethanol) and 264.5 (water). Explain.
(9) At what wavelength the coloured compounds absorb?
(10) Biphenyl shows the following UV absorption data. In its 2, 2' ~imethyl
derivative however, the absorption pattern becomes almost similar to
o-xylene. Explain.

Biphenyl
K-Band, t..max ~ 252,

o-xylene

22

Spectroscopic Data Chemistry


Emax

19,000

"-max 262,

planar conformation

emax 270

(II) How will you confirm the presence of a-diketone system in the following
steroid?

(12) Why the Amax for the diene (I) is observed at lower run than (II)

0-0
(I)

(13) The following triene on partial hydrogenation gives three products.


Which are separated by glc. How UV spectroscopy and application of
Woodward-Fieser rules will help to identify the products.

GO

CO

co co

23

UltravIolet Spectroscopy

Answers to the problems


( I) In compound (I) the unshared electron pair of the nitrogen atom in the
dimethylamino group is conjugated with the benzene ring (n

~ 7t*

conjugation). While in compound (2) this conjugation cannot be


complete owing to the methyl group at the ortho position.
When methyl at the ortho position is replaced by a more bulky group,
namely, isopropyl, the peak wavelength is shifted still further (owing to
full violation of conjugation) to shorter wavelengths (A = 420 nm), with
an accopanying drop of the band intensity (e

18,600).

(2) For isomer 1 we find

A = 215 nm
+ 24 nm (2 x 12)
239nm
For isomer 2 A = 215 nm
+ 12 nm (~-substituent)
+ 18 nm (8-substituent)
+ 30 nm (extra double bond in conjugation)
+ 05 nm (exocyclic double bond)
280nm
Hence, the absorption spectrum hlJS been measured for isomer I.
(3) A bathochromic shift (red shift) may occur by a change of medium or
by the presence of an auxochrome. A hypsochromic shift (blue shift)
may be caused by a change of the medium or by such structural changes
like removal of conjugation.

(4)

)-N

H2

Hel)

~~

')--N

H 3 c\

')--NH3HSO;

Due to the removal of conjugation of the lone pair of electrons on the


nitrogen atom of aniline with the 1t-bond system of the benzene ring on
protonation, the main absorption band is seen at 203 nm (e7500) and is
comparable with benzene.

Spectroscopic Data Chemistry

24

(5) In 0.1 N HCI solution o-Nitrophenol gives a UV band at Amax 350 nm


due to n--1[ conjugation

Conversion of a phenol to the corresponding anion (i.e. in 0.1 N NaOH


solution) results in a bathochromic shift of the E2 and B bands and an
increase in Emax because the nonbonding electrons in the anion are
available for interaction with the 1[ electron system of the ring. Therefore
band is observed at 4 I 5 nm in 0.1 N NaOH soln.

(6) Singlet excited state of the brightening agent is converted into triplet
state which emits radiation in the visible range.
(7) One a-substituent, two (3-ring residues and one exocyclic double bond:
215 + 10 + 24 + 5 = 254 nm.
(8) This is the expected shift of the n ~ 1[* transition of acetone to shorter
wavelength (blue shift) by changing to solvents of increased polarity.

(9) Longer than 400 nm.


(10) Although biphenyl is slightly twisted, the angle of twist is small,
therefore, conjugation between the rings is not affected. Biphenyl thus
shows a very intense absorption band at 252 nm (K-Band). Biphenyl
derivatives with bulky substituents in the ortho positions are more stable
in twisted conformations than in the planar conformation, which suffers
serious non-bonded compressions from the juxtaposed substituents. The
loss of conjugation in the twist conformation of2, 2-dimethylbiphenyl
is reflected in its UV spectral data, which now structurally is like two
moles of o-xylene.
A H

Planar conformation
(A

CH 3 and B = CH)

2,2' --Dimethylbiphenyl

/CH 3

H
Twist conformation

2,2' -dimethylbiphenyl
B-Band "-max 270, Emax 800

25

Ultraviolet Spectroscopy

(II) It will largely exist in the enolic form as revealed by the observed "-max
281 nm ( Emax 9,700) which matches with the Cal. "-max (on enolisation
the double bond becomes exocyclic to one ring). On acetylation the
spectrum is restored to that calculated for the system now with OAC in
the a-position. Further confirmation will come from the measurement
of the spectrum of the enolised form in alkaline solution which will show
; ,

the expected bathochromic shift of some 50 nm, i.e., 281 run ~ 330 run.

HO&O
ObS

max

calc
" " max

= 281 nm (E max 9700)


= 215 + 2

12 + 5 + 35 = 279 run ..

""

A C O O } (215+2 x I2+5+6(OAC)
= 250 run

~
(12) In both the dienes, there are 4 ring residues as substituents. In diene
(II), the two double bonds are exocyclic, thus in it "-max will be higher
by 2 x 5 = 10 run.
(13) The markedly differed values are expected from each of the structures.

1~

~
'\ 'C... 3
exoc

base value
253 run
3 alkyl substituents 3 x 5 15 nm
exocyclic C=C
05 nm
Calculated or expected 273 run
"-max
< 200 11m (not conj)

~k'3
~

1)" "\
exoc

214
15
05
234

run
nm

nrn
nrn

CD

ClClCl

2
Infrared Spectroscopy

Symmetrical' Asymmetrical
Stretching vibrations, U

Scissoring (cry
Rocking (p)
In-plane deformations

Wagging (m)

Twisting ('r)
Out of plane deformations
Bending Vibrations, 8

27

Infrarred Spectroscopy

Table 2.1a: Characteristic infrarred absorption frequencies of common


classes of organic compounds
Type

Vibration
mode

1. Alkanes
-C H3

C-H str., asym.


C-H str., sym.
C-H def., asym.
C-H def., sym.
C-H def.
Skeletal

Frequency.
cm- I
2975-2950

-C(CH 3)3

C-Hdef.
Skeletal

-CH 2-

C-H str., asym.

2880-2860
1470-1435
1385-1370
1385-1365
1175-1140
840-790
1395-1365
1255-1200
750-720
2940-2915

C-H str., sym.

2870-2845

C-H, Scissoring
C-H, twisting &
wagging
Skeletal, if

1480-1440
Ca. 1250

-C(CH3 )2

CH 3
-in cyclopropane
-C-H

-(CH 2 )4 or more
C-H str.
Skeletal
C-H str.
C-H def

Wave
length, Il
3.36-3.39

Relative
intensity*
m.

3.47-3.50
m.
6.80-6.97
s.
7.22-7.30
m., sh.
s., d.
7.22-7.33
8.51-8.77
s., br.
11. 90.12.66
m.
7.17-7.33 s, d. ratio 1:2
s., br., d.
7.97-8.33
s., br.
13.33-13.89
3.40-3.45 m. strong if
several
3.49-3.52
m.-CH 2present
6.76-6.94
m.
Ca. 8.00
m.

750-720

13.33-13.89

s.

3080-3040
1020-1000
2900-2880
Ca. 1340

3.25-3.29
9.80-10.00
3.45-3.47
Ca. 7.45

v.
m.
w.
w.

3310-3300

3.02-3.03

m.

600-650
2140-2100

16.7-15.4
4.67-4.76

s.
w.

2260-2190

4.42-4.57

u.

2. Alkenes
See Table 2.2a & 2.2b
3. Alkynes and allenes C-H str.
Terminal/
monosubstituted
C-H def.
(RC=CH)
C=C str.

Noo!"",'"'''

unsymmetrically
disubstituted
R1C=CR 2

C=C str.

28

Spectroscopic Data Chemistry

c=c type str.,

Allenes (C=C=Cj

antisym.

1970-1950

5.08-5.13

m.

1060

9.43

m.

O-H str.

3650-3590

2.74-2-79

V.,

compounds)

O-H str.

3550-3450

2.82-2.90

v., sh.

Polymeric

O-H str.

3400-3230

2.94-3.10

s., br.

compounds

O-H str.

3570-3450

2.80-2.90

V.,

sh.

chelate compounds

O-H str.

3200-2500

3.1-4.0

W.,

br.

Primary C-O-H

O-H def.

1350-1260

7.40-7.94

s.

C-O str.

1075-1000

9.30-10.00

s.

C-C type str., sym.


4. Aromatic hydrocarbons
See Table 2.3
5. Alcohols and phenols
Free-OH

sh.

Intermolecularly
hydrogen bonded
(Change on dilution)
Dimeric (Single bridge

Intramolecularly
hydrogen ,bonded
(no change on dilution)
single bridge

Secondary C-O-H
Tertiary C-O-H
Phenols

O-H def.

1350-1260

7.40-7.94

s.

C-O str.

1120-1030

8.93-9.71

s.

O-H def.

1410-1310

7.09-7.63

s.

C-O str.

1170-1100

8.55-9.09

s.

O-H def.

1410-1310

7.09-7.63

s.

C-O str.

1230-1140

8.13-8.77

s.

6. Ethers and epoxides


Acyclic CHJ-O-CH J
Aryl and aralkyl

Conjugated

R-O-R str.asym.

1150-1070

8.70-9.35

s.

C-H str.

2830-2815

3.54-3.55

m.

Ar-O-Ar asym.

1260-1200

7.98-8.33

v-s

= C-H str.

3150-3050

3.18-3.28

w.

C-O-C str.

1275-1200

7.84-8.33

\'

Ar-O-R str.,

29

lnfrarred Spectroscopy
C

t-butyl

c-c-o str.

920-800

10.87-12.50

s,

I
C

Cyclic

C-O str.

1140-1070.

8.77-9.35

s,

-O-CH 2-O

C-O str,

Ca, 940

Ca. 10-65

s.
v.

C-H str.

Ca,2780

Ca,3.65

Epoxides

C-O str.

1260-1240

7,94-8.07

s.

trans

C-O str.

950-860

10 53-11.63

cis

C-O str.

865-785

11.56-12,74

v.
m,

7. Carbonyl compounds
For C=O stretching vibrations of acid chlorides, acid anhydrides, carboxylic acids,
esters, aldehydes, ketones, ami des and salts, see tables 2.4 and 2,5,
Vibrations other than C = 0 stretching vibrations

a) Anhydrides
Cyclic

C-O str.

1310- 1210

7,63-8.26

s,

Acyclic

C-O str.

1175-1045

8.51-9,57

s,

Free OH

O-H str.

3550-3500

2.82-286

m,

Bonded OH

O-H str.

3333-2500

3.00-4,00

w" br.

fine structure bands2700-2500

3,70-4-00

w.

v,

b) Carboxylic acids

AIIOH

O-H def.

955-890

10 47-11.24

Solid fatty acids

CH 2 vib.

1350-1180

740-8.48

w.

characteristic
pattern
-COOH

C-O str. plus


O-H def.

Carboxylate ion

1440-1395

6,94-7.17

w.

1320-1210

758-8.26

s,
s
m,

O=C-O str., asym, 1610-1550

6.21-6.45

O=C-O str., sym, 1420-1300

7,04-7,69

Fonnates

C-O str,

1200-1180

8,33-8.48

Acetates

C-O str,

1250-1230

8,00-8.13

s,

C-O str,

1200-1170

8 33-8,55

s,

c) Esters

Propionates and
higher esters

30

Spectroscopic Data Chemistry


Esters of aromatic
C-O str.

1300-1250

7.69-8.00

s.

C-O str.

1220-1200

8.20-8.33

s.

Esters of a, 13 unsat. C-O str.

I310-1250

7.63-8.00

s.

2880-2650

3.47-3.77

w.-m., d.

975-780

10.26-12.82

w.
s.

acids
Vinylic and
phenolic acetates
aliphatic acids
d) Aldehydes

C-H str., asym.

e) Ketones
CH 3 -CO
CH2 -CO-

t) Arnides
primary, free NH

CH 3 def.

1360-1355

7.35-7.38

-CH 2 def.

1435-1405

6.97-7.12

s.

C=O str., overtone 3550-3200

2.82-3.13

w.

3540 - 3480

2.83-2.88

s.

3420-3380

2,92-2.96

s.

3360-3320

2.98-3.01

m.

3220-3180

3.11-3.15

m.

1650-1620

6.06- 6.17

s.

6.17-6.29

s.

2.91-2.93

s.

N-H str.

bonded NH

N-H str.

Free or bonded

N-H def. plus

NH

C-N str.

(amide II band)
1620-1590
(amide II band)
Secondary, free NH
bondedNH

N-H. cis str.

3440-3420

N-H, trans str.

3460-3430

2.89-2.92

s.

N-H, cis str.

3180-3140

3.15-3.19

m.

N-H, trans str.

3330-3270

3.00-3.06

m.

3100-3070

3.23-3.26

w.

Ca.700

Cal4.30

N-H, cis and


trans. str.
N-H def.

(amide V band)
N -H def. plus
C-N str.
Acyclic compound

N-H def. plus


C-N str.

1305-1200

conc.
dependent

7.67-8.33

m.

6.37-6.60

s.

6.45-6.62

s.

(amide III band)


1570-1515
(amide II band)
1550-1510
(amide II band)

31

Infrarred Spectroscopy
770-620

1300-16.13

m.

15.87-18.87

s.

(amide IV band)
630-530
(amide VI band)

8. Amines, amino acids and their salts see table 2.6


9. Unsaturated nitrogen compounds
a) Nitriles
C=Nstr.

2260-2240

4.42-4.46

m.

C=Nstr.

2235-2215

4.47-4.51

S.,V.

Aryl

C=Nstr.

2240-2220

4.46-4.50

m.

Iso-

C=Nstr.

2185-2120

4.52-4.72

s.

1690-1640

5.92-6.10

v.

C=N str.

1665-1630

601-6.14

v.

C=N str.

1660-1480

6.02-6.67

v.

C=Nstr.

1580-1550

6.33-6.45

w.

=C-H str.

3070-3020

3.26-3.31

s.
s.

saturated alkyl

a,

P unsaturated

alkyl

b) Oximes, pyridines, quinolines. purines, pyrimidies elc.


Acyclic saturated, C=N sir.
(alkyl compounds)
Acyclic a,

P unsat.

compounds
Cyclic a,

P unsat.

compound (such as thiazoles)


Pyridines

Ring C-H def.

Ca. 1200

Ca. 8.33

1100-1000

9.09-10.00

s.

C=C str.

1650-1580

6.06-6.35

m.

Pyrimidines and

=C-H str.

3060-3010

3.27-3.32

s.

Purines

Ring C-H def.

1000-960

10.00-10.42

m.

825-775

12.12-12.90

m.

Pyrroles
Oximes

C=N str.

1580-1520

6.33-6.58

m.

N-H sir.

3440-3400

2.91-2.94

m.

C=C sir.

1565-1500

6.39-6.67

v.. d.

C=N str.

1690-1620

5.92-6.17

v.

O-H Sir.

3650-3500

2.74-2.86

v
v.

Azo compounds

-N=N sir.

1630-1575

6.14-6.35

Carbodiimides

-N=C=N str.

2155-2130

4.64-4.70

s.

Isocyanates

-N=C=O sir

2275-2240

4.40-4.46

s. -v.

Azides

-N=N=N sir

2170-2080

4.61-481

s.

32

Spectroscopic Data Chemistry

10. Compounds containing nitrogen-oxygen bond


Nitrates (O-NOzl.

N0 2 str.. asym

1590-1500

nitramines.nitro
N0 2. str.. sym.
(compounds CC-N0 2) C-N vib.

1390-1250

720-8.00

920-830

1088-12.05

6.29-6.67

s.
\\.

m .. -s

Nitroso compounds

(R-C-N=O)

alkyl, aromatic

N=O str.

1550-1500

6.45-6.67

s.

(a-halogeno. aliphatic N=O str.

1620-1560

6. I 7-6.47

s.
v. Os,

Nitrites (R-O-N=O)
trans form

N=O str.

1680-1650

5.95-6.05

N-O str.

815-750

1227-13.33

625-565

16.00-17.70

1625-1610

6.16-6.21

O-N=O def.
Cis form

Nitrosamines

N=Ostr.

s.
s.
V.,

s.

N-O str.

850-810

1I. 76- I 2.35

O-N=O def.

690-615

14.49- I 6.26

s.

overtone

3360-3220

2.98-3.11

m.

N=O str.

1500-1480

6.67-6.76

s.Vapor

1460-1440

6.85-6.94

s. solution

N-N str.

Ca. 1050

Ca. 9.52

s.

N-N = 0 def.

Ca. 660

Ca. 15.15

s.

N-O str.

1310-1250

7.63-8.00

moo-s.

SoH str.

2600-2550

3.85-3.92

W.
W.

s.

phase
(R-N-N=O)

phase

Azoxy compo
(R-N-N-O)
11. Sulfur compounds

CoS str.

700-570

14.18-17.54

C= S str.

1675-1130

5.97-8.85

S.

Thioketone

C= S str.

1250-1020

8.0-9.8

Thioamide

C= S str.

1300-1I00

7.69-9.9

S.

Covalent sylfates

S=O str., sym ..

1440-1350

6.94-7.41

S.

(RO)z S02
Covalent sylfonates

S=O str., as)'m.

1230-1I50

8.13-8.70

S.

S=O str. sym.

1420- 1330

7.04-752

S.

(R,-O-S02-R2)
Sulfonyl chlorides

S=O str.. asym.

1200-II45

8.33-8.73

S.

S=O str., sym.

1375-1340

7.27-7.46

S.

(R-SOzCI)
Sylfonamides

S=O str.. asym.

I 190-II60

8.40-8.62

s.

S=O str.. sym.

1370-1300

7.30-7.69

S.

33

Inti-arred Spectroscopy
(R-S02-N)

s=o str. asym.

1180-1140

8.48- 8.77

s.

Sulfones

S=O Str., Sym.

1350-1300

7.41-7.69

v.. -so

(R2S0 2)

S=O str.. asym

1160-1120

862-8.93

v., -so

Sylfonic acids

S=O str.. sym.

1260-1150

7.94-8.70

s.

(RS0 3 H)

S=O str.. asym.

1080-1010

9.26-9.90

s.

Sylfites (RO)2S0

S=O str.

1220-1170

8.20-8.55

s.

Sylfoxides (R-SO-R) S=O str.

1070-1030

9.35-9.71

s.

O-H str.

2700-2560

3.70-3.90

w.

P-H str.

2440-2350

4.10-4.26

m.

P-C def.

1450-1280

6.90-7.81

m.-s.

P=O str.

1350-1150

7.41-8.70

v.-s.

P-O str.

1240-900

8.07-10.10

v.

P-O str.

1000-870

s.

-700

w.

P-O-C (aJiph)

1050-970

s.

830-740

s. (may be absent)

P-O-C (arom)

1260-1160

s.

994-855

s.

12. Phosphorus compounds

P-OH

P-O-P

13. Halogen compounds

Polyfluorinated

C-F str.

1400-1100

7.14-9.10

v.

-S.,

mit.

v. -s .. d.

Difluorinated

C-F str.

1250-1050

8.00-9.50

Monofluorinated

C-F str.

1110-1000

9.01-10.00

s.

Polychlorinated

C-CI str.

800-700

12.50-14.30

v. -so

C-CI equatorial

C-CI str

780-750

12.80-13.33

s.

C-CI axial, other

C-CI str.

Ca. 650

Ca. 15.40

s.

monochlorinated
C-Br equatorial

C-Br str.

750-700

13.33-14.29

s.

C-Br axial

C-Br str.

690-550

14.50-18.20

s.

Other monobromides

C-Br str.

650-560

15.40-17.85

s.

Iodides

C-I str.

Ca. 500

Ca. 20.00

s.

2220-1600

4.51-6.25

v.. mIt.

B-C def.

1460-1280

6.85-7.81

v.

Si-H str.

2280-2080

4.39-4.81

v.-s.

Si-H def.

800-950

12.5-10.53

14. Silicon and boron compounds

B-H str.

s.

34

Spectroscopic Data Chemistry

SIOH

str. *=stretching

O-H str.

3700-3200

2.7-3 12

s.

Si-O

830-11 10

12.05-9.01

s.

Si-F str.

800-1000

12.5-10.0

Si-C def.

Ca. 1260

Ca. 7.94

v. -so

Si-C str.

840-755

11.90-13.25

V.-s.

sym. =symmetric

s=strong absorption

w=weak absorption

def. = deformation asym.=asymmetric m.=medium absorption v.=variable intensity


sh.=sharp peak

d.=doublet

br.=broad absorption

mlt.=multiplet

Table 2.1b Correlations of infrared absorption and structure of organic


compounds
Frequency Wavelength Intensity Type and group
range

Bond

range

4000-3001
3676-3584

2.72-2.79

V.,

3650-3496

2.74-2.86

v.

3595-3425

2.78-2.92

V.,

sh.

sh.

Alcohols, phenols,
free OH

O-H str.

Oximes (R-C = NOH)

O-H str.

R-OH, Ar-OH,
intramolecular hydrogen
bonded

O-H str.

3550-3500

2.82-2.86

m.

3550-3450

2.82-2.90

Y. sh.

R-OH, Ar-OH, dimeric

O-H str.

3550-3205

2.82-3.12

w.

Ketones, C=O overtone

C=O str.
N-H str.

Carboxylic acids,
free OH

3540-3380

2.83-2.96

s., d.

Primary amides, free NH

3500-3300

2.86-3.03

V., d.

Primary amines,

3460-3435

2.89-2.91

s.

3360-3220

2.98-3.11

m.

3440-3420

2.91-2.93

s.

O-H str.

free NH secondary amines

N-H str.

Sec. amides, free NH (trans)

N-H str.

Nitrites (R-O-N=O)
overtones

N=O str.

Sec. ami des, free


NH(cis)

N-H str.

3440-3400

2.91-2.94

m.

Pyrroles

N-H str.

3400-3300

2.94-3.03

v.

Imines

N-H str.

3400-3230

2.94-3.10

s., br.

R-OH, Ar-OI-{'
polymeric

O-H str.

35

Infrarred Spectroscopy

3400-3200

2.94-3 13

m. d

Amino acid salts

3400-3095

2.94-3.23

m.

Amines. imines.
associated

N-H str.

3390-3255

2.95-3.07

m.

Amido acids

N--H str.

3380-3150

2.96-3.18

m.. mit.

Charged amine

3360-3180
3330-3270

2.97-3.15
3.00-3.06

m.. d.
m.

NH, str.

derivatives

NW 3 str.

Amides, bonded NH

N-H str.

(primary)

N-H str.

Sec. amides. bonded


(trans)

N-H str.

3310-3300

3.02-3.03

m.

Alkynes (RC=CH)

C-H str.

3300-2500

3.00-4.00

W"

br.

R-COOH, bonded OH

O-H str.

3200-1700

3.13-5.88

w., br.

R-OH, Ar-OH. chelate

O-H str.

3175-3135

3.15-3.19

m.

Sec. ami des, bonded


NH (cis)

3150-3050

3.18-3.28

w.

N-H str.

Ethers -CH=C-Oand C=CH-O-

C-H str.

3130-3030

3.20-3.30

m.

Amino acids,
hydrochlorides

NH3+ str.

Ca. 3100

ca. 3.23

v.

Tropolones

O-H str.

3100-3070

3.23-3.26

w.

Amides, bon. NH (cis)

3095-3075

3.23-3.25

m.

Alkenes (CHR=CH z)

3085-3040

3.24-3.29

v.

N-H str.
RC-H str.

Alkanes (-CH z-'


cyclopropane)

3085-3030

3.24-3.30

w.-m, mit.

3075-3020

3.25-3.31

s.

3060-3010

3.27-3.32

s.

C-H str.

Aromatic homocyclic
(=C-H)

C-H str.

Pyridines. quinolines
(=C-H)

C-H str.

Pyrimidines. purines
(=C-H)

3050-2995

3.28-3.34

w.

Ethers. epoxides

3040-3010

3.29-3 32

Alkenes (CHR=CH z'


CHR 1=CHR z' cis

3030-2500

3.30-4.00

\v.

mit.

or trans. CR1Rz=CH z)
Amino acid
hydrochlorides

C-H str.
OC-H str.

C-H str.

Spectroscopic Data Chemistry

36

3000-2001
2975-2950

3.36-3.39

m.

Alkanes (-CH J )

C-H str.

2940-2915

3.40-3.43

m.

Alkanes (-CH z-)

C-H str.

2905-2875

3.44-3.48

w.

Alkanes (-CH-) .

C-H str.

2880-2860

3.47-3.50

m.

Alkanes (-CH J )

C-H str.

2880-2650

3.47-3.77

w.-m., d.

Aldehydes (-CHO)

C-H str.

2870-2845

3.49-3.52

m.

Alkanes (-CH 2-)

C-H str.

m.

Ethers (-O-CH l )

C-H str.

2835-2815

3.53-3.55

Ca. 2825

ca. 3.54

m.

Alkyl acetals

C-H str.

2825-2760

3.54-3.62

m.-s.

Amines (N-methyl)

C-H str.

2780-2400

3.60-4.17

v.
v.

Deuterated R-OH,
Ar-OH

O-D str.

Ethers (O-CH 2-O-)

C-H str.

ca. 2780

ca. 3.60

2760-2530

3.62-3.95

w.

Amino acids

ca. 2700

ca. 3.70

s.

Charged amine

NH2 + rck.

derivatives
Organo-phosphorus

2700-2560

3.70-3.90

w., b.

2640-2360

3.79-4.24

w.

Amido acids,

2600-2400

3.85-4.15

v.

Deutcrated amines,

2590-2550

3.86-3.92

w.

Orga.no-sulfur
compounds
Charged amines

S-H str.

(C=NW)

NH+ str.

compounds

N-D str.

imines

2500-2325

4.00-4.30

s.

2280-2260

4.39-4.43

s.

2280-2080

4.39-4.81

v.

O-H str,

Diazonium salts
(R-C=N=Nt
Organo-silicon
compounds

Si-H str.
N=C=O str.

2275-2240

4.40-4.46

v.

isocyanates

2260-2240

4.43-4.46

w.-m.

Saturated nitrites

C=N str.

2240-2220

4.46-4.51

m.-s.

Aryl nitrites

C=N str.

2235-2215

4.47-4.52

s.

Acyclic u.

2220-1600

4.51-6.25

v.. mIt.

2200-1800

4.55-5.56

w.-m.

P unsat.

nitriles

C=N str.

Boron compounds

B-H str.

Charged amine
derivatives

NWvib.

37

Infrarred Spectroscopy
2185-2120

4.58-4.72

s.

Isonitriles

2\60-2120

4.63-4.72

s.

Azides (-N=N=N)

2155-2150

4.64-4.69

s.

Carbodiimides

2140-2100

4.67-4.76
4.67-4.8\

Ca. 2100

ca. 4.76

w.
w.
w.

Alkynes (RC""CH)

2140-2080

Deuterated alkanes

ca. 2000

ca. 5.00

w.

Amino acid

1970-1950

5.08-5.13

m.

Allenes (C=C=C)

1945-1835

5.14-5.45

w.

Amido acids

1870-1830

5.35-5.46

s.

Acid anhydrides,

1850-18 \0

5.40-5.53

s.

Acid anhydrides, conj.

1850-\800

5.40-5.56

m.

Alkenes (CHR=CH 2)

Amino acids

C""N str
--N=N;=N str.
N=C=N str.
C""C str.
NH)' str.
C-D str.

2000-1501
hydrochlorides

5 ring
5 ring

C""C type str.

C=O str.
C=O str.

overtone

C-H str.

\840-1800

5.44-5.56

s.

Acid anhydride, acyclic

C=O str.

1820-18\0

5.50-5.53

s.

Acyl peroxides

C=O str.

1820-1780

5.50-5.62

s.

conj.acyclic acid

C=O str.

1815-1785

5.51-5.60

s.

Acid halides

\805-1780

5.54-5.62

s.

Aroyl peroxides
esters. lactone

C=O str.

1800-1780

5.56-5.62

s.

(R-CO-O-)2

C=O str.

1800-1780

5.56-5.62

Alkenes (CR 1 R2 =CH 2),


overtone

C-H str.

1800-1770

5.56-5.65

s.

Conj. acid halides

C=O str.

1800-1770

5.56-5.65

s.

Vinylic phenolic esters

C=O str.

1800--1760 5.56-5.68

s.

Acid anhydride, 5 ring

C=O str.

1795-1740

s.

Acid anhydrides, conj.

anhydrides

5.57-5.75

5 ring
1790-1720

5.59-5.81

s.

1785-1755

5.60-5-70

s.

1780-1770

5.62-5.65

s.

C=O str.

C=O str.

Ureas (-CO-NH-CO-),
amide I

C=O str

(RCO-O-)2

C=O str.

Fused - ring p lactams,


amide I

C=O str.

38

Spectroscopic Data Chemistry

1780-1760

5.62-5.68

s.

Ketones. 4 ring, sat.


y lactone

C=O str.

1780-1740

5.62-5.75

s.

Acychc acid anhydrides

C=O str.

1760-1730

5.68-5.78

s.

Simple

Plactams

C=O str.

1760-1720

5.68-5.81

s.

Conj. acyclic anhydrides

C=O str.

1755-1740

5.70-5.75

s.

a keto esters, a diesters

C=Ostr.

1755-1730

5.70-5.78

s.

a-amino acid hydrochloride

C=O str.

1755-1720

5.70-5.81

s.

Dicarboxylic a-amino acids

C=O str.

1750-1740

5.71-5.75

s.

Ketones. 5 ring

C=O str.

1750- 1735

5.71-5.76

s.

y-keto esters, diesters,

i750-1735

5.71-5.76

s.

Sat. aliphatic esters,


a-Iactones

C=O str.

1745-1725

5.73-5.80

CO-O-CH 2-C0-

C=O str.

1750-1700

5.71-5.88

s.
s.

Fused ring y lactams

C=O str.

i740-1720

5.75-5-81

s.

Sat. aliphatic aldehydes

C=O str.

1740-1715

5.75-5.83

s.

a-halogeno carboxylic acids

C=O str.

1735- 1700

5.76-5.88

s.

Urethanes

C=O str.

1730-1710

5.78-5.85

s.

-CO-CO-

C=O str.

1730-1700

5.78-5.88

s.

Amino acid hydrochlorides

C=O str.

1730-1715

5.78-5.83

s.

a,

1730-1700

5.78-5.88

s.

Dicarboxylic amino acids

C=O str.

1725-1705

5.80-5.87
5.80-5.88

s.

-CO-CH 2-CH 2-C0Sat. aliphatic acids,

C=O str.

nonenolic p-keto esters

1725-1700

s.

Punsat., aryl esters

C=O str.

C=O str.

dimer, acyclic,
1725-1695

5.80-5-90

s.

CH 2-CO-CH 2-ketones
a-amido acids

C=Ostr.
C=O str.

1720-1700

5.81-5.88

s.

Ketones, 6-ring

C=O str.

1715-1700

5.83-5.88

s.

Ketones. 7-ring

C=O str.

1715.1695

5.83-5.90

s.

Aryl aldehydes

C=O str.

1715-1680

5.83-5.95

s.

a, 13 unsat, acids

C=O str.

1710-1690

5.85-5.92

s.

Carbamates. amide I band

C=O str.

1710-1670

5.85-5.99

s.

-CO-NH-CO-, amide
I band

C=O str.

1705-1685
ca. 1700

5.78-5.93
ca. 5.88

s.
s.

a, 13 unsat. aldehydes
Simple y lactams. amide

c=o str.

I band

C=O str

39

Infrarred Spe.ctroscopy
1700-1680

588-5.95

s.

Aryl carbo,ylic acids.

('=0 str.

1700-1665

5.88-6.01

dimer. aryl k.etones

('=0 str.

secondary' amide.
amide I bind
1695-1660

5.90-6.02

s.

ex,

P unsat. acyclic

or 6 ring ketones
ca. 1690

ca. 5.92

s.

C=O str.

Primary amides, amide


I band

C=O str.

1690-1670

5.92-5.99

W.

5.92-5.99

s.

CR IR 2=CR 3R4 , a1kenes


o-hydroxy (amino)

C=C str.

1690-1670

benzoates

C=O str.

1690-1655

5.92-6-04

s.

Quinones, 2 CO's in

1690-1635

5.92-6-01

v.

oximes, oxazines, oxazo1ines,

C=O str.

same ring
oxazolones, azomethines,
acyclic C=N

C=N str.

ca. 1680

ca. 5.95

s.

Large-ring cyclic lactams

C=O str.

1680-1660

5.95-6.02

s.

Conj. polyene aldehydes

C=O str.

1680-1650

5.95-6-06

s.

Intramolecular H-bonded
carboxylic acids

C=O str.

Nitrites (R-O--N=O trans)

N=O str.

1680-1650

5.95-6.06

v.

1680-1630

5.95-6-14

s.

sec. amides, amide I band

C=O str.

1680-1620

5.95-6.17

v.

Nonconj. alkenes

C=C str.

1675-1665

5.97-6.00

v.

Alkenes, CR IR2=CHR 3

C=C str.

ca. 1675

ca. 5.97

s.

Thioesters

C=S str.
C=O str.

1670-1660

5.99-6

Cross-conj. dienones

1670-1645

5.99-6.08

s.

Intramolecular
OH

I
H-bonded (-C=C-CHO
type) aldehydes
1670-1630

5.99-6.14

s.

Tertiary amides. amIde

1665-1635

6.01-612

v.

Alkenes

I band

1665-1630

6.01-614

v.

C=O str.
C=O str

(CHR,=CHR 2 -<:is)

C=C str..

Oximes. Oxazines. etc.

C=N str.

Spectroscopic Data Chemistry

40

ca. 1660

ca. 6.02

s.

Urcas (NH....CO ....NI-I).


amide I band

c=o str

1660-1640

6.02-6. \0

v.

Alkenes (CR 1R2 =CH 2 )

C=C Str.

1660-16\0

6.02-6-21

w.

Amino acids
containing NH2 group.
amino acid I band

1660-1580

6.02-6.33

s.

NH3+ def.

Alkenes conj. with


C=O orC=C

1660-1480

6.02-6.76

v.

C=C str.

Thiazoles (cyclic a.13


sat. C=N)

1655-1635

6.04-6.12

s.

C=N str.

Enolic l3-keto esters.


chelated

C=O str.

1655-1635

6.04-6.12

s.

Quinones, 2 CO's in

1655-1610

6.04-6.21

s.

o--CO-C 6 H4--OH (or

1655-16\0

6.04-6.21

s.

ca. 1650

ca. 6.06

s.

Primary amides. amide

1650-1590

6.06-6.31

s.

Prim. amides. amide

2 rings

C=O str.

NH 2), H....bonded

C=O str.

Nitrates (RON0 2 ),
asym. vibration

N0 2 str.

I band

c=o str.

II band, combination
NH def. + CN str. NH def. + CN str.
1650-1620

6.06-6.17

s.

Amido acids, amide

1650-1580

6.06-6.33

m.

pyrimidines, quinolines

1650-1580

6.06-6.33

m.-s.

Prim. amines

NH def.

1650-1550

6.06.-6.45

w.

Sec. amines

NH def.

1645-1640

6.08-6.\0

v.

Alkenes (CHR=CH2)

C=C str.

1640-1605

6.10-6.23

s.

Alkyl nitroguanidines,

C=C + C =N str.

I band-

asym. N0 2 vibrations
1640-1535

6.\0-6.52

s .. d.

N0 2 str.

Ketones (....CO-CH 2....CO


or ....CO-C=C--OH)

C=O str.
N=N str.

1630-1575

6.14-6.35

v.

Azo compounds

ca. 1625

ca. 6.16

s.

Alkene~,

phenyl

conj. C=C

C=C str.

41

Infrarred Spectroscopy
1625-1610

6.16-6.21

v.

Nitrites (RON=O cis

1625-1575

6.16-6.35

v.

Aromatic homocyclic

N=Ostr.

form)

C=C i-p vib.

compo
1620-1600

6.17-6.25

S.

Tropolo!)es

1620-1600

6.17-6.25

S.

Amido acids. amide

C=O str.

I band
1620-1590

6.17-6.31

s.

Prim. ami des, amide

NH def. +

II band. combination

CNstr.

NH def. + CN str.
1620-1560

6.17-6.41

s.

Nitroso compounds,

1620-1560

6.17-6.41

m.-s.

u halogeno
Charged amine derivatives

N=N str.
NH 2+ def.

1610-1590

6.21-6.29

W.

Amino acid hydrochlorides

NH3+ def.

1610-1550

6.21-'6.45

s.

Carboxylate ion,

Ca. 1600

ca. 6.25

m.

asym. str.
Charged amine derivatives

1600-1575

6.25-6.35

s.

u. u -dihalogenonitro

s.

compounds
Amino acid salts,

V.

all amino acids


with ionized carboxyl
Aromatic homocyclic

1600-1560

1590-1575

6.15-6.41

6.29-636

compo C=C
1590-1575
1585-1530
1580-1570
1580-1550

6.29-6.36
6.31-6.54

S.

6.33-637

S.

6.33-6.45

S.

W.

NH3+ def.
N0 2 str.

c=o str.
i-p str.

Nitroureas
Saturated nitramines
u-halogenonitro

N0 2 str.
N0 2 str.

compounds

N0 2 str.

Nitrogen heterocycles,'
combination, C= C
and C=N str.

1580-1520

1570-1515

6.33-6.58

6.37-6.60

m.

Pyrimidines and

S.

purines, combination,
C=C and C=N str.
Sec. acyclic amides,

C=C + C=N str..

C=C+C=N str.

amide II band,
combination NH def.
and CN str.

NH def. + CN str

42
1570-1500

Spectroscopic Data Chemistry

6.37-6.67

s.

All amido acids, amido


II band

N-H def.
C=C str.

ca. 1565

ca. 6.39

v.

Pyrroles

1565-1545

6.39-6.47

s.

Prim. and sec. nitro


N02 str.

compounds
ca. 1550

ca. 6.45

s.

Tertiary aliphatic
nitroso compounds,
N=O str.

vapor phase
1550-1510

6.45-6.62

s.

1550-1485

6.45-6.73

v.

Aromatic nitro compounds


Amino acids cont.
NHz group, amino acid
II band

1550-1510

6.45-6.62

s.

Sec. acyclic ami des,


ami des II band

1550-1485

6.45-6.73

v.

NH3+ def.
NH def. + eN str.

Amino acid
hydrochlorides

1545-1530

6.47-6.54

s.

Tert. nitro compounds

1530-1510

6.54-6.62

s.

a, l3-unsat. nitro
compounds

1525-1475

6.56-6.78

v.

6.62-6.76

m.

N02 str.

aromatic homocyclic
compo C=C

1510-1480

NH/ def.
N0 2 str.

i-p vib.

Pyridines, qui no lines,


combination C=C and
C=N str.

C=C+C=N str.

ca. 1500

ca. 6.67

v.

Pyrroles

C=C str.

ca. 1500

ca. 6.67

S.

Aromatic nitroso
compounds

N=O str.

ca. 6.67

S.

Amine saIts

NH def.

1500-1440

6.67-6.94

S.

Nitrosamines (RNN=O)

N=O str.

ca. 1500
1500-1001
1485-1445

6.74-6.92

m.

Alkanes (-CH 2-)

C-H def.

1470-1430

6.80-7.00

m.

Alkanes (-CH 3 )

C-H def.

ca. 1467

ca. 6.81

m.

Alkanes, CH 2 scissor

C-H def.

ca. 1460

ca. 6.85

m.

Alkanes. asym CH 3

C-H def.

1455 (ca.)

ca. 6.87

m.

Alkanes, alicyclic CH 2

ca. 1450

ca. 6.90

m.

scissor
Aromatic multiple bond

C-H def.
C=C str.

43

Infrarred Spectroscopy
1430-1400

7.0-7.14

v.

Ketones, esters,
a-methylene C-H sCissor

1430-1350
1420-1410

7.00-7.41
7.04-7-09

s.
s.

Sulfites
Alkenes (RCH=CH 2

1420-1390

7.04-7.20

w.

or R,~C=CH2)
Alcohols

1410-1310

7.10-7.60

s.

1400-1300
1400-1000
1395-1385

7.15-7.69
7.15-10.0
7.17-7.22

s.
s.
m.,d.

1390-1360

7.20-7.35

m.,d.

1380-1370
1380-1310

7.25-7.30
7.25-7.30

s.
s.

1370-1340
1370-1300
ca. 1365
1360-1310
1350-1300
1350-1280

7.30-7.46
7.30-7.70
ca. 7.33
735-7.64
7.41-7.69
7.41-7.81

1350-1260
ca. 1340
1340-1250

7.41-7.94
ca. 7.46
7.46-8.00

s.
s.
s.
s.
s.
s.
s.
w.
s.

1340-1180
1335-1310
1310-1295

7.46-8.48
7.39-7.64
7.64-7.72

w.

v.
m.

1300-1250
1275-1200

7.70-8.00
7.84-8.33

s.
v.

ca. 1270
1260-1200
1257-1232

ca. 7.88
7.94-8.33
7.95-8.12

v.
v.
v.

Phenols, tert.
alcohols
Carboxylic acids, ionic
Halogen comp., fluorides
Alkane, tert. butyl
'Alkane, geminal dimethyl,
isopropyl, tert. butyl sym.
CH 3 bending
Alkane,-C~

C-H def.
S=O str.
C-H def.
O-H def.
O-H def.
C-F str.
C-H def.

CH3 def.
C-H def.

Aliphatic nitro
compounds
Sulfonyl chlorides
Nomatic nitro compounds
Alkane, tert. butyl
Aromatic tert. amines
Sulfones, sulfonamides
Aromatic sec. amines
Prim. and sec. alcohols
Alkanes
Aromatic prim.
amines
Azides
Sulfur compounds
Alkene (R,CH=CHR2)
trans
Nitrates
Conj. ethers

N0 2 str.
S=O str.
N0 2 str.
C-Hdef.
C-N vib.
S= 0 str.
C-N vib.
O-H def.
C-H def.
C-N vib.
-N3 str.
S=O str.
C-H def.
O-N0 2 vib.
ROR str.

//

Aromatic esters
Aromatic ethers
Aliphatic esters,
CH)COOR

-C...Q--R str.
R-O-Ar str.

44

Spectroscopic Data Chemistry

1255-1200

7.97-833

S.,

1240-1190

8.06-8.40

>.

compo

P-O str.

1230-1150
1210-1150

8.13-8.70

S.

Sulfites

S=O str.

8.27-8.70

S.

8.20-9.80

\Y.

Sulfonic acids
Aliphatic amines

S=O str.

1220-1020
ca. 1200

ca. 8.33

S.

Phenols

C-O str.

1200-1050

8.33-9.52

S.

Sulfur compounds

C=S str.

d.

Alkanes, tert. butyl

Skeletal str.

Aromatic phosphorus

C-N vib.

1200-1190

8.33-8.40

V.

Esters (RCOOR)

1185-1175
1185-1165
1l80-1140

8.44-8.51
8.44-8.59
8.48-8.77

V.

S.

Esters (H-COOR)
Sulfonyl chlorides

S.

Sulfonamides

1l75-1l40

8.51-8.77

S.

1175-1l55

8.51-8.65

V.

Alkanes, geminal dimethyl skeletal vib.


Methyl esters (R-COOCH 3 )

1175-1125

8.51-8.89

W.

S=O str.
S=O str.

Substituted benzenes,
1, 3-disubstituted or
tri-substituted benzens

1160-1140

8.62-8.77

S.

Sulfones

ca. 1150

ca. 8.70

S.

Tertiary alcohols

1150-1070
1120-1100

8.70-9.35

V.

8.93-9.09
9.35-9.71

S.

1070-1030

Aliphatic ethers
Secondary alcohols
Sulfoxides

ca. 1060
1060-1030

ca. 9.40
9.43-9.71

m.

1075-1010

9.30-9.90

1050-990
1000-501
995-985

S.

C-H def.
S=O str.
C-OH str.
R-O-R str.
C-OH str.
S=O str.

S.

Allene (C=C=C)
Sulfonic acids

S=O str.

V.

Primary alcohols

C-OH str.

9.52-10.1

V.

Phosphorus compounds

10.05-10.15

S.

Monosubstituted alkenes
(RCH=CH z)
Disubstituted alkenes
(R 1CH=CHR2) trans

C-H def.

P-O str.

C-H def.

970-960

10.31-10.42

S.

915-905

10.93-11.05

S.

Monosubstituted alkenes
(RCH=CH z)

C-H def.

900-860

11.11-11.63

m.

Tetra-or penta-substituted
benzene containing I free H

C-H def.

895-885

11.l7-11.30

S.

Geminal disubstituted
alkene

C-H def.

45

Infrarred Spectroscopy
885-870

11.30-11.50

1,2,4-trisubstituted benzene.

m.

C-H def.

another peak at 852-805


ca. 870

1 \.50 (Ca.)

m.

Pentasubstituted

870-800

1\.50-12.50

v.

Benzene ring

C-H def.

benzene
containing two adjacent
840-790

II. 90-12.66

s.

810-750

12.34-13.34

v.

800-600

12.50-16.67

s.

770-735

12.98-13.61

V.,

H atoms

C-H def.

Trisubstitutated alkenes

C-H def.

Benzene ring with three

s.

adjacent H atoms

C-H def.

Halides

C-Cl str.

Benzene ring with


four adjacent free H
C-H def.

atoms
770-730

12.98-13.70

V.,

s.

Benzene ring with five


adjacent free H atoms,
C-H def.

second peak at
710-690
ca. 690

ca. 14.50

s.

Disubstituted alkenes
C-H def

(R 1CH=CHR2) cis
ca. 650

ca. 15.40

s.

Sulfonic acids

ca. 630

ca. 15.90

s.

Alkynes

600-500

16.60-20.00

s.

Bromides

ca. 500

ca. 20.00

s.

Iodides

s=o str.
C-H def.
C-Br str.
C-I str.

s=strong absorption

v.=variable intensity

vib.=vibrating

bon.=bonded

m.=medium absorption

sh.=sharp peak

d.=doublet

sat. =saturated

w.=weak absorption

br.=broad absorption

mlt.=multiplet

Table 2.2a: Infrarred absorption frequencies of alkenes


Vibration mode

Alkene type

Frequency,
cm- I

RCH=CH z (Vinyl)
H

'R)C=C<H

Wave

Relative

length,11 intensity

C-H str. (CH z)


C-H str. (CHR)

3095-3075

3.23-3.25

3040-3010

3.29-3.32

Overtone

1850-1800

5.40-5.56

m
m
m

C=C str.

1645-1640

6.08-6.10

46

Spectroscopic Data Chemistry


CH 2 i-p def.

1430-1410

CH i-p def.

7.00-7.10

1300-1290

7.69-7.75

CH o-o-p def.

995-985

10.05-10.15

CH 2 <H>-p def.

915-905

10.93-11.05

C-H str.

3040-3010

3.29-3.32

C=C str.

1665-1635

C-H i-pdef.

1430-1400

6.01-6.12
7.00-7.14

730-665

13.70-15.04

R,CH=CHRz(cis)
H
H
)c=c<
R,
Rz

C-H <H>-p def


R,CH=CHRz (trans)
R,) C=C <H
H

Rz

C-H str.

3040-3010

3.29-3.32

C=C str.

1675-1665

5.97-6.01

C-H i-pdef.
C-H <H>-p def.

1310-1290 7.63-7.75
980-960 10.20-10.42

3095-3075

R,R2C=CH2 (Vinylidine)
R,)

C-H str.
<H
C=C
H(gem) overtone
C=C str.
CH 2 i-p def.

1800-1780
1660-1640
1420-1410

3.23-3.25
5.56-5.62
6.02-6.10
7.04-7.09

m
v
w

895-885
11.17-11.30
3040-3010 3.29-3.32

C-H <H>-p def.

1675-1665 5.97-6.01
840-790 11.90-12.66

v
m

R,) C=C <~

C= C str.

1690-1670

5.92-5.99

~
R4
Ar-HC=CH 2
C=OorC=C

C=C str.

~1625

~.16

C=C str.

1660-1580

6.02-6.33

R,RzC=CH~

(Trisubstituted)
R,) C=C <H

CHz o---o.-p def.


C-H str.
C=;C str.

R,RzC=C~R4

(Tetrasubstituted)

Conjugated with
C=C

Abbreviations: str. = stretching, i-p def. = in-plane deformation, ()-{r-P def. = out of
plane deformation, s = strong, m = medium, w = weak, v = variable.

47

Infrared Spectroscopy

Table 2.2b: C=C Stretching frequencies in cyclic and acyclic systems cm- 1

"'cH
C/ -<C

Ring or Chain
Chain cis
Chain trans
Three membered ring
Four membered ring
Five membered ring
Six membered ring
Seven membered ring
Eight membered ring

1661
1676
1641
1566
1611
1649
1651
1653

)<:H, c;C~

1681

_<CH
C

>~H'
1661
1780
1678
1657
1651

1672
1890
1685
1686
1685

1658
1678
1673

All rings have cis double bond:;


Table 2.3: Absorotion frequencies typical of aromatic homocyclic compounds:
Arormatic

Vibration

compound

mode

Frequency,
em-I

Monsubstituted

=C-H sir.
(Multiple bands)

3080-3030

3.24-3.33

(five adjacent
hydrogen atoms)

C=C str. (rmg


stretching)

1604 3

6.25-6.22

1585 3

6.31-6.30

1510~1480

1452 4

6.62 ~6.75
6.87-6.91

v
v

1177 6(2.5 vs 3,6)

8.45-8.54

w
w

C-H i-p def.

C-H o-o-p def.


I, 2-Disubstituted
(four adjacent
hydrogen atoms)

=C-H str (multiple


bands)
C=C slr. (nng
stretching)
C-H I-P def.

Wave-

Relative

length,l!

Intensity

1156 5(3,5 vs 4)

8.61-8.69

1073 4(2.6 vs 3,4,5)


1027 3(2,3 vs 5,6)

9.28-9.36
9.71-977

751 15

13.06-13.58

691 1\

14 1-1458

w-m

w
s

3080-3030

324-3.33

w-m

1607 9
1577 4

6.26-619
633-636

v
v

1510~

1460
1447 10

6.85-662

6.87-696

7.77-799

1269 17
(all c1ock\llse)

48

Spectroscopic Data Chemistry


1160 4(3,5 vs 4,6)

859-865

1125 1"4(3,6 vs 4,5)

8 78-90

1033 11(3,4 vs 5, 6)

958-978

751 7

13 20-13 44

3080-3030

324-3.33

C-H o-o-p def.


I 3 - Disubstltuted

=C-H str.

(three adJacent

(multiple bands)

hydrogen atoms)

C=Cstr
(ring stretching)

1600~

1620

1586 5

C-H i-p def

6.17

629-6.32

v
v

1470

6.69

6 80

1465 ~ 1430
1278 12 (all

6.83

6.99

1495

6 25

w-m

7.75-7.90

clockwise)

C'-H o-o-p def

1157 5 (2, 5 vs 4, 6)

8.60-8.68

1096 7 (4 vs 6)

9.07-9.\8

1076+7(2 vs s)
900 ~ 869 (I free H)

9.23-9.36

II 12-11.63

782 10 (3 adj H Wag)

12.82-12.96

725

680 (3 adj. H wag) 13.79-14.71


3.24-3.33

m
w-m

6.20-6.25

631-6.36

v
v

1:4 Disubstltuted
(two adjacent

=C-H str (multiple


bands)

hydrogen atoms)

C=C str. (ring


stretching)

1579 6
1520~ 1480
1409 8

658~6.76

7.05-715

C-H I-P def

1258 II (all clockwise)

7.88-802

1175 6 (2, 5 vs 3,6)


1117 7 (2, 6 vs 3,5)

w
w

8.90-9.01

9.82-9.92
12.02-12.47

3080-3030
1606 6

1013 5 (2, 3 vs 5,6)


C-H o-o-p def
1:2:3- Trisubstituted =C-H str.
(multiple bands)
C..l.H i-p def

817 15
3080-3030
1175
1110

~
~

1125
1070

1070 ~ 1000
C-H o-o-p def.
1:2.4-Trisubstltuted

=C-H str (multiple

847-8.56

3.24-3.33
8.51
9.01

~
~

8.90
9.35

9.35 ~ 10.00
10.00 ~ 10.42

1000 ~ 960
800 ~ 770

12.50

12.99

720~

13 90

14.60

685

w-m
w
w
w
w
m

3080-3030

324-333

w-m

C=C str (ring

1616 8

stretching)

1577 8
1510 8

6 15-6.22
631-637

v
v

660-6.66

686-688

bands)

14S6 I

49

Infrarred Spectroscopy
C-H I-P def

816~851

1175~

1125

8.51

~889

1090

8 89

1125

1070 ~ 1000
C-H lH>-p def
1.3.5-Trisubstltuted

=C-H str

1225~1175

10 00

860

ILl I

\I 63

860 ~ 800

1163

12.50

900~

9 35

918

324-333

3080-3030

w-m

(multiple bands)
C-H i-p def.

1l75~1125
1070~

C-H lH>-p def.

Tetrasubstltuted

(multiple bands)
C-H lH>-p def

w
w

1l1l~1163

11.56 ~ 12.30

865
=C-H str.

900 --l "CO


810

730 ~ 675
1:2:3 :4-

8.51~889

10.00

1000

9.35

13 70

3080-3030
860 ~ 800

1:2:3:5; I :2'4.5 and

=C-H sIr.

1:2:3:4:5

(multiple bands)

3080-3030

C-H lH>-p def

900~

14.82

324-333
II 63

w-m

1250

3.24-3.33

w-m

substituted

The symbol 151 0

860

ILl I

11.63

1480 indicates the range, in cm- of absorption uf radiation. Usually

an electron donor substitutent causes absorption near 1510 cm- I , while an electron acceptor
substitutent causes absorption near 148{) cm- I .
Abbreviations: str. = stretchmg, i-p def. = in plane deformation, lH>-p def. = out of plane
deformation, w = weak, m = medium,s = strong, v = variable, ad]. = adjacent. wag = wagging.

Table 2.4: C = 0 stretching frequencies of carbonyl compounds


Type of carbonyl
Compound

Typical examples (phase)

C=O st_
fre. cm- I

Value of
absorption
wavelength, ~

Acid anhydrides
(RCOOCOR)
a. Saturated, acyclic
Acetic anhydride (CCI 4 )

1850-1800

5.41-5.56

1790-1740

5.59-5.75

1825 and 1754 5.48 and 5.70

b. Saturated, 5-

1870-1820

5.35-5.49

membered ring

1800-1750

5.56-5.71

Succinic anhydride(CHC1)

1820 and 1776 5.49 and 5.63

50
c. a,

Spectroscopic Data Chemistry

p- Unsaturated

and aryl, acyclic


d. a,

1830-1780

5.47-5-62
1770-1720
5.65-5-81
Benzoic anhydride (CHCI) 1818 and 1740 5.50 and 5.75

p- Unsaturated,

1850-1800

5.41-5.56

1830-1780

5.47-5-62

-1850

-5.41

-1795

-5.57

1812

5.52

1792
-1810
1780-1750
1750-1720(m)

5.58
-5.53
5.61-5.72
5.72-5.82

c. Acyl bromides
d. a, p- Unsaturated
and aryl
Benzoyl chloride (CCI 4 )

1739

5.75

e. COF 2
f. COCI 2

1928
1828

5.19
5.47

g. COBrz
Carboxylic acids
(RCOOH)dimers
a. Saturated aliphatic

1828

5.47

1725-1700

5.80-5.88

1775
1760

5.63
5.68

1721

5.81

1724
1698

5.80
5.89
5.83-5.92

5 membered ring
Acid halides (RCOX)

a. Acyl fluorides
b'. Acyl chlorides

Acetyl chloride (CCI 4 )


Isovaleryl chloride (Film)

Butyric acid
(monomer) (CCI 4 )
Acetic acid (CCI 4 )
Butyric acid (Film)
a- chloropropionic acid (Film)

n- Hexanoic acid (Film)


b. a,

p- unsaturated

1715-1690

aliphatic
c. aryl
Benzoic acid (KBrl
Salicylic acid (KBr)
Esters (RCOOR)
a. Saturated, acyclic

1700-1680
1678
1665

5.88-5.95

1750-1735

5.71-5.76

5.96
6.01

51

Infrarred Spectroscopy
Methyl acetate (CC 1~)

1750

5.71

Methyl propionate (CCI 4 )

1748

5.72

Ethyl propionate (CCI 4 )

1736

5.76

Propyl formate (CCI 4 )

1733

5.77

o-lactones (and larger rings)

1750-1735

5.71-5.76

y-lactones

1780-1760

5.62-5.68

~-lactones

-1820

-5.5

1800-1770

5.56-5.65

b. Saturated, cyclic

c. Unsaturated
vinyl ester type
Vinyl acetate (CCI4 )
a,

~-

unsaturated and aryl


Ethyl cinnamate (CCI 4 )

a,

~-unsaturated

~-y-unsaturated

y-Iactone

y-lactone

d. a-keto esters
e.

~-keto

esters (enolic)

f. Carbonates

1765

5.68

1730-1717

5.78-5.82

1710

5.85

1760-1740

5.68-5.75

-1800

-5.56

1755-1740

5.70-5.75

-1650

-6.06

1780-1740

5.62-5.75

Aldehydes (RCHO)
a. Saturated, aliphatic

1740-1720

5.75-5.81

n-butanal (CCI 4 )

1736

5.76

Acetaldehyde (CCI4 )

1730

5.78

Valeraldehyde (CCI 4 )

1730

5.78

lsovaleraldehyde (Film)
o-Chlorobenzaldehyde (Film)

1715

5.83

1695

5.90

b. a,

~-

Unsaturated, aliphatic

1705-1680

5;87-5.95

c. a,

~-

y- 0- Unsaturated, aliphatic

1680-1660

5.95-6.02

1715-1695

5.83-5.90

1690

5.92

1725-1705

5.80-5.87

d. Aryl

p-anisaldehyde (CCI 4 )
CCI 4

Ketones (RCOR)
a. Saturated acyclic
Butanone (CCI 4 )

1724

5.80

Acetone (CCI 4 )

1720

5.81

2-Pentanone (CCI 4 )
Methyl isopropyl ketone Film

1712

5.84

1709

5.85

52

Spectroscopic Data Chemistry

b. Saturated, cyclic
6-membered ring (and higher)

1725-1705

5.80-5.87

5-membered ring

1750-1740

5.71-5.75

4-membered ring

-1775

-5.63

1685-1665

5.94-6.01

1686

5.93

6-membered ring (and higher)

1685-1665

5.94-6.01

5-membered ring

1725-1708

5.80-5.85

e- a, ~, a I, ~ I ,-Unsaturated,

1670-1663

5.99-6.01

1700-1680

5.88-5.95

1686

5.93

1670-1660

5.99-6.02

1669

5.99

h. a- Diketones

1730-1710

5.78-5.85

i. ~-Diketones (enolic)
j. 1, 4-Quinones

1640-1540

6.10-6.50

1690-1660

5.92-6.02

-2150

-4.65

-1650

-6.06

-1690

-5.92

c. a,

~-

d. a,

~-Unsaturated,

Unsaturated, acyclic
Methyl vinyl ketone (CCI 4 )
cyclic

acyclic
f. Aryl

propiophenone (CCI4 )
g. Diaryl
Benzophenone (CHCI 3)

k. Ketenes
Amides

a. Primary (RCONH 2 )
solid and concentrated solution
dilute solution
Acetamide (CHCI 3)

1670 and shoulder 5.97 and


at 1716

5.83 (sh.)

1680-1630

5.95-6.14

1700-1670

5.88-5.99

b. Secondary (RCONHR)
solid and concentrated
solution
dilute solution

N-methyl acetamide (CCI 4) 1675and shoulder 5.97and


c. Tertiary, solid and all solutions
N, N-dimethyI-{CCI 4 )
acetamide

at 1705

5.86 (sh.)

1670-1630

5.99-6.14

1660 and shoulder 6.02 and


at 1710

5.85 (sh.)

53

Infrarred Spectroscopy
d. Cyclic, o-Iactams, dilute solution

-1680

-5.95

e. Cyclic, y-Iactams, dilute solution

-1700

-5.88

1750-1700

5.71-5.88

1760-1730

5.68-5.78

1780-1770

5.62-5.65

i. Ureas, acyclic

-1660

-6.02

j. Ureas, cyclic, 6 membered ring

-1640

-6.10

k. Ureas, cyclic, 5-membered ring

-1720

-5.81

1740-1690

5.75-5.92

-1710

-5.85

-1700

-5.88

-1710

-5.85

f. Cyclic, y-Iactams, fused to


another ring, dilute solution
g. Cyclic,

~-Iactams,

dilute solution

h. Cyclic,

~-lactams,

fused to another ring,

dilute solution

1. Urethanes
m. Imides, acyclic
n. Imides, cyclic, 6-membered ring
o. Imides, cyclic, ex,

~-

-1730

-5.78

6-membered ring

unsaturated,

-1670

-5.99

p. Imides, cyclic,

-1770

-5.65

5-membered ring
q. Imides, cyclic, ex,

~-

unsaturated, 5-membered ring

-1700

-5.88

-1790

-5.59

-1710

-5.85

Table 2.5: Variation in frequency of vibrations of carbonyl stretching


bands due to inter and intramolecular factors
Add cm-I

Shift to higher
frequency
Basic value in CCI4

1720

Shift to lower
frequency

Substract
cm- I

Neat solid or liquid state

10

Solvent
Hydrocarbon solvents

CHCI 3, CHBr3, CH 3 CN
(partially polar)

Ring strain
Angle decreases 6

15

Ring strain
~

5 ring

35

Angle increases 6
to 10 ring

7
10

54

Spectroscopic Data Chemistry

15

Bridged systems

Substitution on a-carbon

Substitution on'a-carbon

Each alkyl group

(Field and inductive effects)

Alkyl groups substituted


by amine

Substituent cis oriented and


Coplanar

20

-CI, -Br, -OR


-OH, and -OAe
Substituent trans and

5
-NHMe (monosubstituted amide) 30
-NMe2 (disubstituted amide)
55
-NH2 (amide)

Intramolecular hydrogen bonding


Nil

Weak: a or

~-OH

ketone

nonplanar

Medium: o-OH arylketone

Alkyl group substituted by

Strong : ~-diketone

electronegative atoms or groups

Intermolecular hydrogen bonding

-H (aldehyde)
-OR (ester)
-OH (monomeric acid)
-O-C=C (vinyl ester)

10
25
40
50

Weak: ROH ..... O=C<


Strong: RCOOH dimer

10
40
100
15
45

conjugation (depends
on stereochemistry)

-CI (acid chloride)


-OCOR (anhydrides)

90
100

Second C=C

30
15

Third C=C

Nil

Benzene ring

20

FirstC=C

Vinylogous,
-CO-C=C-X(X=HorO)

40

5'

Table 2.6: Vibration modes of amines and amino acids (frequency in em-I)
Compound

N-H stretching
asym

Primary amines

sym

N-H

C-N

C=O

C-O

:
Other vibrations

deformation

stretching

stretching

stretching

and remarks

3550-3350

3450-3250

1650-1580

1220-1020 (ali)

Shoulder at 3200

(2.82-2.99f..l)

(2.90-3.08f..l)

(6.06-6.33f..l)

(8.2-9.8f..l)

(3. 12f..l), overtone of

1340-1250 (aro)

1610 (6.21f..l) band

(7.46-8.0f..l)

N-H wagging strong

=t>

.,.,

III

(1)

Q..

C/l

"0

.,...

(1)

(")

Vl
(")

0
"0

'<

band at 850-750
(11.76-13.34f..l)
Scondary amines

3550-3350

1650-1550

1350-1280 aro

N-H wagging strong

(2.82-2.99f..l)

(6.06-6.45f..l)

(7.4 1-7.8 1f..l)

band at 750-700
(13.34-! 4.29f..l) -N-H
def. band often masked
by aromatic band in
aromatic compounds

Tertiary amines

1380-1260 aro

N-Me band in secon-

(7.24-7.94f..l)

dary and tertiary.


amines, observed at
2820-2760 (3.543.62f..l)

Amine

About 3380,

About 1600

hydrochloride

(2.96f..l)

(6.25f..l) asym.

chloride

NH\ str.

VI
VI

Compound
Charged amine
derivatives

Primary amino
acids

N-H stretching
asym
sym

N-H
deformation

About 3280,
(3.05J.l) NW 3 str.
3350-3150, NH\ str.
(2.99-3.17J.l) (l2.5J.l)
NW 3 solid phase
3125-3030
(3.2-3.3J.l)

About 1300
(7.7J.l) sym.
About 800
rock

CoN
stretching

1660-1610 band I
(6.02-6.2 I J.l)
1550-1485 band II
(6.45-6.74J.l)

Dicarboxylic amino
acids
Amino acid
hydrochlorides

Amino acid
sodium salts

3130-3030
(3.2-3.3J.l)

3400-3200
(2.94-3.13J.l)
Two bands

1610-1590 band I
(6.21-6.29J.l)
1550-1480 band II
(6.45-6.75J.!)

C=O
stretching

C-O
stretching

1600-1560 ionized
(6.25-6.41J.l)
carboxyl str.

Other vibrations

VI

0-

and remarks

Weak band at 27602530 (3.62-3.96J.l)


Medium band at 1300
(7.69J.l)

1755-1720
(5.7-5.81J.l)
unionised carboxyl str.
1755-1730
1230-1215 Series of bands
(5.7-5.78J.l)
(8.13-8.23J.l) between 3030 and
Unionised
2500 (3.3 and 4.0J.l)
carboxyl str.
1600-1560
(6.25-6.14J.l)
ionised carboxyl

r/)

"0
0

..,.....

(')

til
(')

0
tJ

n'

.....

I:Il
I:Il

(1

::r
0

3
Vi'
.....

Infrarred Spectroscopy

57

Table-2.7: Infrared Transmission characteristics of selected solvents and


Mulling Oils
(Transmission below 80% obtained with a 0-10 mm cell path is given in cm I)
Solvent

Acetone

Absorption
(em-I)
3480-3340,3180-2730,1890-1060,940-880,
805-790, 600-630

Acetonitrile

3260-2800, 2340-2180, 1600-1310, 11 001000,980-900,815-740,630-600

Benzene

3150-2960,2000-1935, 1860-1790,
1545,
1500,1445-1365,1190-1140,1070-980,865845, 600-750

Benzonitrile

3150-2960, 2280-2160, 2000-1890, 16401285, 1215-1165, 1100-1000, 960-915, 600820

Bis-2-(methyl ethyl) ether

3150-2580, 2000-1930, 1545-815, 600-635

Bromoform

3060-2960, 1190-1100, 600-800

Bromotrichloromethane

600-840

Butyl acetate

3150-2800, 1935-815, 780-755, 600-680

I-Butanol

3600-2500, 1600-600

Dibutyl ether

3040-2580, 1540-810, 775-740, 630-600

Carbondisulfide

2360-2100, 1625-1410,690-600

Carbon tetrachloride

1570-1520,840-720,690-600

Chloroform

3060-2960,1250-1180,945-935,830-600

Cyclohexane

3040-2580, 1510-1410, 1285-1250, 10601020, 910-860, 680-600

58

Spectroscopic Data Chemistry

Solvent

Absorption
(em-I)

CycIopentane

3060-2730, 1520-1410, 1340-1310,925-870,


645-600

1,2-Dichloroethane

3150-2960, 1500-1435, 1370-1230, 10501070,975-875,765-600

Diethyl ether

3060-2600,2000-1965, 1525-1000, 960-895,


870-790, 635-600

1,4-Dioxane

3060-2650,2000-1965, 1460-1075,940-825,
690-600

Dodecane

3060-2650, 1460-1290,755-695,665-600

Hexane

3060-2650, 1525-1330, 900-885, 780-720,


635-600

Tetrachloro ethylene

1060-1035,960-885,830-745,680-600

1,1-Trichloro-trifluoroethane

1415-1345, 1270-780, 700-600

2,2,4-Trimethylpentane

3040-2550, 1520-1175, 1000-975,645-600

Water

3650-2930, 1750-1580, 930-600

Mulling Oils

Absorption
(em-I)

Nujol

3030-2860, 1460-1386, 720

Hexachlorobutadiene

1650-1500,1280-1200, 1020-760

Fluorolube

1350-650

Problems: (I) The IR spectrum of an organic compound CgH7N shows


the following bands:
3030(w); 2920(w); 2217(s); 1607(m); 1607(m); 1508(m); 817(s)

Infrarred Spectroscopy

59

What is its structure?


CgH7N Index = 6* (Probably aromatic)

[For a molecule (CwHxNyOz, the total number of rings and double bonds
is obtained by the formula R = 112 (2w -x + y ~ 2)
Here M.F.

CgH7N = R = 1/2 (16 -7 + I + 2) = 6.

The presence of one benzene ring in the structure requires atleast four
unsaturation sites (3 double bonds + I ring)]
3030 cm- I ; 1607 cm- I ; 1508 cm- I aromatic 2217 cm- I ; CN rather than
C=C which gives a weak band CN, C7H7 Index 2
The band at 2920 cm- I is weak. Since alkyl groups give a strong band in
this region, it may be concluded that such groups are absent or are very few in
number. This is supported by the fact that CN accounts for an index value of2
and the remaining index (4) must be in the C7H7 unit. This, can be a heptatriene
or a phenyl ring. But the presence of a band at 2920 cm- I , though weak, indicates
the presence of atIeast one alkyl unit, hence heptatriene ring is absent and
C7H7 is a toluyl unit. The very st~ong band at 817 cm- I may be ascribed to out
of plane bending vibrations of two -ArH atoms and hence, the compound is a
p-disubstituted benzene and the structure of the compound is

CH3~N p-toluonitrile
(2) Identify the structure of the compound CgHgO whose spectrum
contains the following absorption bands:
1680(s), 1600(m), 1580(m), 1450(m), 1430(s), 1360(s), 1265(s), 755(s),
690(s) cm- I .
The empirical formula suggests the following structure for the
compound:

~O
C H--C
6

""

CH3

Spectroscopic Data Chemistry

60

The IR spectral bands agree with this structure. The monosubstituted


benzene ring has the characteristic bands at 1600, 1580, 1450, 750 and 690
cm- I , the characteristic bands for the aromatic ketone are at 1680 and 1275
cm- I , and those for the methyl group are at 1430 and 1360 cm- I.
(3) Deduce the structure:
CsHIS IR bands (cm- I) 2960; 2860; 1460;
1395; 1385;
1375; 1365
Several bands in fmger print region, i.e., a branched alkane. The latter
four bands are two doublets- indicating isopropyl and tert-butyl groups

Therefore, the compound is

2,2,4-trimethylpentane

(4) From the following examples, we can readily see the usefulness of
Table 2.5 in predicting the values ofC=O absorption bands. The wavenumbers

for

c=o stretching vibrations for a number of compounds are calculated as

follows:
a. Benzophenone in chloroform

Basic value for c=o absorption

1720 em-I

Shift due to benzene rings 2 x 20

-40 em-I

Shift due to solvent CHCI3

- 15 em-I

-------------------------------1665 em-I
Calculated
Observed

1669 em-I

61

Infrarred Spectroscopy
b. Vinyl propionate in CCI 4

~o

-C""

CH3CH 2

OCH=CH2
Basic value for C=O absorption
Vinyl ester (-O-C=C) shift
Alkyl group on a carbon

1720 cm- 1
f- 50 cm- 1
- 5 cm- 1

-C~a~lc-u~la-t-ed~---------------1~7~6~5-c-m~1

Observed

1760 cm- 1

c. Acetic anhydride in CCl4

Basic value for c=o absorption


1720 cm- 1
Anhydride (-O-COR)
+ 100 cm- 1
----------------------------~1
Calculated
1820 cmObserved
1825 cm- 1
d. Benzamide in CHC~

o
\I

r5~
Basic value for C=O absorption
1720 cm- 1
- 5 cm- 1
Alkyl group substituted by NH2
Alkyl group substituted by benzene
- 20 cm- 1
Solvent polarity effect .t
- 15 cm- 1
Hydrogen bonding about
- 15 cm- 1
----------------------------~
Calculated
1665 cm- 1
Observed
1667 cm- 1

62

Spectroscopic Data Chemistry


e. Caprolactam neat liquid
CH -CH --NH

./'

CH 2
~

CH 2-CH 2--C=0

Basic value for C=O absorption

1720 cm- I

Alkyl group substituted by NHMe

- 30 cm- I
-5 cm- I

Alkyl group on a carbon


seven member ring

-lOcm- 1

Neat liquid

-10 cm- I
Calculated

1665 cm- I

Observed

1667 cm- I

(5) Suppose that you are investigating a compound with the molecular
formula C4H60 2 You find that it contains an ester carbonyl and -ene group.
You determine this on the basis of the following bands in the IR spectrum ofa
CCI 4 solution of the compound. 3030 cm- I (weak), 1765 cm- I (strong), 1649
cm- I (strong), 1225 cm- I (strong) and 1140 cm- I (strong). IdentifY these bands,
write all the possible structures which include these two groups, and identifY
the compound.
Answer: Identification of the bands:
3030 cm- I C-H str. in terminal RHC=CH 2 (CHR group)
1765 cm- I C=O str.
1649 cm- I C=C str. (terminal)
1225 cm- I C-O-C str. (asym.)
1140 cm- I C-O-C str. (sym.)
For a compound with the molecular formula C4H602' only two structures
with an -ene and an ester carbonyl group can be written.
-:::;:::0
methyl acrylate (an a,
(a) CH 2 = CH-C
--"0 - CH 3 unsatur~ted ester)
(b) CH 3

-:::::-0
C--..
vinyl acetate
OCH =CH 2

~-

63

Infrarred Spectroscopy
The two structures can be distinguished on the basis of their
stretching frequencies. We ean calculate

c---o stretching frequency

co-o

in each

ease

a)

b)

Basic value

1720 em

OR (ester)

+ 25 em I

conjugation (C=C)

- 30 em I

Calculated

1715 cm

Basic value

1720 cm-l

-O-C=C (vinyl ester)

+ 50

Calculated

1770 em-I

since the observed value is


1765 em-I the compound is (b)

ClCHJ

Proton Magnetic Resonance


Spectroscopy

Aliphatic alicyclic
I
I
p-substituted aliphatic

I----l
Alkyne

a-Monosubstituted aliphatic
I
I
a-Disubstituted aliphatic
Alkene
Aromatic and heteroaromatic
I
I
Aldehydic

I---i

IO

General regions of chemical shifts

Proton Magnetic Resonance Spectroscopy

65

3.1 Effect on shift positions of a single functional group


Table 3.1: Chemical Shifts of Methyl, Methylene and Methine protons (a
to the functional groups) in 0
CH~X

-CH~X

-CHX

0.23

0.90

1.25

CH 30rCH 2-

0.86

1.2

1.55

C=C-

1.6

2.1

C=C-

1.7

2.2

2.8

Ph

2.25

2.6

2.85

4.26

4.45

4.8

CI

3.05

3.5

4.05

Br

2.7

3.4

4.1

2.16

3.15

4.25

3.2

3.4

3.8

Functional group X

OH
OR

3.2

3.4

3.6

OPh

3.82

4.05

4.55

OCOR

3.62

4.1

4.95

OCOPh

3.82

4.2

5.05

OTs*

3.7

3.9

4.65 .

CHO

2.2

2.39

2.5

COR

2.1

2.35

2.64

C-OPh

2.4

2.74

34

COOH

2.1

2.3

2.54

COOR

2.0

2.25

2.5

CONR2

2.0

2.26

2.4

C=N

2.15

2.45

2.85

NH2

2.52

2.7

3.04

NR2
NPhR

2.22

2.4

2.84

2.6

3.04

3.6

N"R.

2.95

3.04

3.6

NHCOR

2.95

3.34

3.8

.'

66

Spectroscopic Data Chemistry

Functional group X

-CHX

N02

4.08

4.15

4.4

N=C

2.92

3.3

4.9

N=C=O

3.3

O-C=N

4.6

N=C=S

3.4

3.7

4.0

S-C=N

2.72

3.0

3.3

O-N=O

4.8

SH

2.1

2.6

3.1

SR

2.1

2.6

3.12

SPh

2.52

SSR

2.4

2.72

SOR

2.6

3.1

S02 R

3.1
3.0

S03 R

2.4

P~

PTCI3

3.32

3.4

PO~

2.4

PSR z

2.8

o
OTs is

-O-~

D'

r'

II~

H3

67

Proton Magnetic Resonance Spectroscopy

Table 3.2: Chemical shifts of Methyl, Methylene and Methine protons (~to the functional groups) in 0
Functional group X

CHJ-C-X -CH2-C-X -CH-C-X

CH 2-

0.86

1.2

1.55

C=C-

1.0

1.36

1.76

C=C-

1.2

1.5

1.8

Ph

1.16

1.55

1.8

1.55

1.85

2.15

Cl

1.55

1.8

1.95

Br

1.8

1.85

1.9

1.76

1.8

2.1

OH

1.2

1.5

1.76

OR

1.2

1.5

1.76

OPh

1.3

1.55

2.0

OCOR

1.3

1.6

1.8

OCOPh

1.65

1.75

1.95

OCOCF3

1.4

1.65

CHO

1.1

1.65

COR

1.05

1.55

1.95

COPh

1.16

1.56

1.9

COOR

1.16

1.7

1.9

CON~

1.1

1.5

1.8

C=N

1.25

1.65

2.0

N~

1.05

1.45

1.7

NPhR

1.1

1.5

1.8

NR,+
,

1.4

1.75

2.05

NHCOR

1.1

1.5

1.9

N02

1.61

2.05

2.5

SH

1.3

1.6

1.66

SR

1.25

1.6

1.9

68

Spectroscopic Data Chemistry

3.2 Effect on chemical shifts of two or three functional groups:


(Y-CHz-Z and Y-CH-Z)

I
W
Shoolery's rules permit calculation of a shift position of a methylene group
attached to two functional groups by the additive effect ofthe shielding constants
in Table 3.3. The sum of the constants is added to cS 0.23, the position for CH 4

cS = 0.23 + Lcri
Thus, to calculate the shift for the -CHz- protons ofC 6HFH zBr

C6HS

1.85

Br

2.33
4.18
0.23
4.41

add CH 4

Table 3.3: Shielding constants


Functional group
YorZ

Shielding Constants
cri

CH 3
C=C

0.47

C=C
Ph
CFz
CF3

1.44
1.85
1.21

CI
Br
I
OH
OR
OPh
OCOR
COR
COPh
COOR
CONH z
CONRz
C=N

1.32

1.14
2.53
2.33

.1.82
2.56
2.36
3.23
3.13
1.70

1.84
1.55
1.53
1.59

1.70

69

Proton Magnetic Resonance Spectroscopy

Functional group

Shielding Constants
cri

YorZ
N~

1.57
4.44
2.90
1.70
2.27
1.97
1.64
3.13

N02

N=C=S
C=C-Ar
NHCOR

N3
SR

The shielding constants were used to prepare the following chart 3.3.1.

r. ."."

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2.17 U. 140

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,.co

-CC-<)).

c...

4.U ".02

U,

J.oI

J.OI

..... ... .... ...


.... 4." '.1' ..,!
....
,."
,to
....
'.JO
'"

.s. ."
L..

J.41

c..,
, ,... ""
U,

3M C" .. U
UJ
l.l .. J.1t ,.co
11S

Ul

-<10"",0.

I.OJ 11J

2... 1.0' 1"


'.01
.11

U,

,.11

' ...1

-c(-<>1oPI& u,
-C(aO)OR

J.U
US

'.11

SAl

U,

1.17

... c.,.

J . .,

).)1 1. '

,.,

J.30

-C(=OlH--..

U1

4.10

1.12

l,Jl

-<ooN ~
-Hit,

U1

.OJ

... ,." ,,,,

us ".os

,Jt

H'

..Tt

~
It.
J.n

J.ll

'J1
~~t=4.'7

,n

-NItC{-o. c" .45


-H,

1"

....

..!!.!~

-..

70

Spectroscopic Data Chemistry


This chart can be used to find the shift position of a methylene -roup

attached to two functional groups from the 8 values in the box at the intersection
of the horizontal and diagonal groups ("mileage chart"). The upper number in
each box is an experimental value; the lower number is calculated from
shoolery's constants.
Table 3.4 can be used to calculate chemical shifts of methyl
(Y-CH 3), methylene (Y-CH 2-Z), or methine (Y-CH-Z) groups.

I
W
a

P
I

Thus, the CH 2 chemical shifts in BrCH zCHpCHFH 2 Br can be


calculated.
CH 2 No.1
CH 2 (Table 3, 4, footnote a)

1.20

a-OR

2.35

p-Br

0.60
4.15

CH z No.2
CH 2

1.20

a-Br

2.18

P-OR

0.15
3.53

Determined: CH 2 No.1 at ~8 3.80;


CH 2 No.2 at ~8 3.40
Table 3.4: Substitutent Effects on Chemical Shift C-C-H

I I

Pa
Substituent

-c=C-

Type of Hydrogen" Alpha shift

Beta shift

0.78
0.75

0.10

71

Proton Magnetic Resonance Spectroscopy


Type of Hydrogen" Alpha shift

Substituent

--C=C-C-R

CK

1.08

X
(X=C orO)

CH 3

Aryl

CH 2

II

-I

Cl:i3
CH 2
CH

-OH

CK
CH 2
CH
CH 3
CH 2
CH

lAO
IA5
1.33
2A3
2.30
2.55
1.80
2.18
2.68
1.28
1.95
2.75
2.50
2.30
2.20
2A3
2.35
2.00

CK
CH 2
CH

2.88
2.98
3.43 (esters only)

CH
CK
CH 2
CH
CH 3
CH 2
CH

-CI

-Br

-OR (R is saturated)

II

II

-O-C-R, -O-C-OR
-OAr

Beta shift

0.35
0.53
0.63
0.53
0.03
0.83
0.60
0.25
1.23
0.58
0.00
0.33
0.13
0.33
0.15

0.38
0.43

II
-CR, Where R is alkyl,
aryl, OH, OR', H, CO, orN

1.23
CK
CH 2
1.05
CH
1.05
-NRR'
1.30
CH}
CH 2
1.33
CH
1.33
standard positions are CH 1, I) 0.87; CH 2 , 8 1.20; CR 8 1.55.
0

0.18
0.3\
0.13
0.13

72

Spectroscopic Data Chemistry

3.3: Chemical Shifts in Alicyclic and Heterocyclic Rings


Table 3.5: Chemical shifts in Alicyclic Rings

0.22

o
!

1.96

000
1.51

1.78

1.65

1.44

1.54

G6

02

1.96

22
.
-1.8

2.06

3.03

2.02

-1.8

~.30

U,~1.94

-1.52

-1.52

Table 3.6: Chemical Shifts in Heterocyclic Rings


2.54

V
1.62

HO.03

0
0

2.72

2.23

G 0
0.59 0
85

3.75

4.73
H
2

151
3.52

1.50

.38

3.54

2.75
H 2.01

150
2.74

H 1.84

73

Proton Magnetic Resonance Spectroscopy

2.27

3.17

3.43

R 0J
X

H
4.75-4.90

1.68

1.93

0
S

2.82

3.9-4.1
3.9-4.1

4.70

3.80

2 . 0 8 n 4.38

2.31 yO

1.62
1.62(14.06
2.27

<H

(0

3.4: Chemical Shifts in Unsaturated and Aromatic Systems

R~
CIS

"""

/C=

R trans

Rgem

oH = 5.25 + ~zi
i.e. 5.25 + Zgem + Zcis + Ztrans

For example, the chemical shifts of the alkene protons in

C6H~

/OC 2Hs

C
Ha /

-c:....
-

"'-Hb

are calculated

74

Spectroscopic Data Chemistry

Ha

1.35
-1.28
0.07
l.l8
-0.10
1.08

Hb

5.25
0.07
0,5.32
5.25
1.08
06.33

Table 3.7: Substituent Constants (Z) for chemical shifts of substituted


Ethylenes (in CCI4)
Substituent R
gem

Z
cis

trans

-H
-Alkyl
-Alkyl ring"
-CHp,-CH2 1
-CH 2 S
-CHFI, -CH2Br
-CH 2N
-C=C
-C=N
-C=C
-C=C conjb
-C=O
-C=O conjb
-COOH
-COOH con?
-COOR
-COORconjb

0
0.44
0.71
0.67
0.53
0.72
0.66
0.50
0.23
0.98
1.26
1.10
1.06
1.00
0.69
0.84
0.68

0
-0.26
-0.33
-0.02
-0.15
0.12
-0.05
0.35
0.78
-0.04
0.08
l.l3
1.01
1.35
0.97
U5
1.02

0
-0.29
-0.30
-0.07
-0.15
0.07
-0.23
0.10
0.58
-0.21
0.01
0.81
0.95
0.74
0.39
0.56
0.33

/H
-C=O

1.03

0.97

1.21

/N
-C=O

1.37

0.93

0.35

/CI
-C=O

1.10

-OR, R: aliph

1.18

1.41
-1.06

0.99
-1.28

75

Proton Magnetic Resonance Spectroscopy


-OR, R: Conjb

1.14

-0.65

-1.05

-OCOR

2.09

-0.40

-0.67

-Aromatic

1.35

0.37

-0.10

-CI

1.00

0.19

0.03

-Sr

1.04

0.40

0.55

R: aliph

0.69

-1.19

-1.31

R: Conjb

2.30

-0.73

-0.81

-SR

1.00

-0.24

-0.04

- S02

1.58

1.15

0.95

/R
-N

\R
jR
-N

\R

Alkyl ring indicates that the double bond is part of the ring

The Z factor for the conjugated substitutent is used when either the
substitutent or the double bond is further conjugated with other groups.

Table 3.8: Chemical Shifts of Miscellaneous Alkenes


5,70

RCH

650

502

= CR-CH = CH 2

6.01

608

716

CH 3 -CH = CH-CH

5.62

= CH-COOC 2 H5

Spectroscopic Data Chemistry

76

CH 3CH 2 COSiMe,

II

CH 2
3.92

~"7

~Ol2.
1.92

0 0
0

560
.

5.95

65
1.

5.8

2.15

2.90

h- 5.9

J:j2.00
3.58

6.40

2.66"11 6 . 10

CH
3

6.75

2 . 2 n 7.71

5.59

2.28

6 .42

1.96

57

9
a

2.13

6.88
5.93

77

Proton Magnetic Resonance Spectroscopy


2.66

5.78

2.,53'----'i 4.82

143~) 4.2~)

()
_
I 14.6~

6.22 3.97

~I 6.37

,4,63

6.16

.
US
6.94

3.34

r(jf)4.83

6.IS

~~6.8~

r---j-- 7.63
,-----_._-

61\.

4.92

~2

7.

98

H3~~

H
4.53

<20

7.72
10

2.4
1.41 ,

.~

11

Table 3.9: Chemical Shifts of Alkyne Protons


HC=CR
HC=C-COH
HC=C-C=CR
HC=CH
HC=CAr
HC=C-C=CR

1.73-1.88
2.23
1.95
1.80
2.71-3.37
2.60-3.10

Table 3.10: Chemical Shifts of Protons on Monosubstituted Benzene Rings


Benzene
CH 3 (omp)
CH3 CH z (omp)
(CH 3)FH (omp)
(CH 3)3 C (0, m, p)
C = CH z (omp)
C=CH 0, (mp)
Phenyl 0, m, p
CF 3 (omp)
CH, CI (omp)
CHCl, (omp)
CCL 0, (mp)
J

7.25
7.16
7.16
7.16
7.32, 7.17, 7.04
7.25
7.44, 7.25
7.44,7.25,7.16
7.50
7.25
7.36
8.10,7.50

78

Spectroscopic Data Chemistry

CH 2 OH (omp)
CH,OR (omp)
CH; OCOCH3 (omp)
CH 2 NH2 (omp)
Fm,p,o
Cl (omp)
Br, 0, (pm)
1o, p, m
OHm,p,o
ORm, (op)
OCOCH3 (mp),
OTs (mp),
CHOo,p,m
COCHp,(mp)
COOHo,p, m
COORo,p, m
COClo, p, m
C=N
NH2, m,p,o
N(CH3)2 m (op)
NHCORo
NH 3+0
N02 0,p, m
SR (omp)
N=C=O (omp)
OTs = P - Toluenesulfonyloxy group

7.16
7.25
7.25
7.32
7.25, 7.04,6.95
7.25
7.51,7.25
7.71, 7.25, 7.04
7.04, 6.90, 6.75
7.36,7.00
7.25, 7.04
7.25, 7.04
7.95, 7.64, 7.50
7.90,7.55
7.90, 7.44, 7.36
8.16,7.55,7.44
8.10,7.55,7.44
7.55
7.16,6.84,6.50
7.16,6.70
7.50
7.64

8.23, 7.71, 7.55


7.25
7.04

Table 3.11: Chemical shifts of protons on fused aromatic rings


7.81
8.31
7.91

7.39

7.88
7.82
8.12

79

Proton Magnetic Resonance Spectroscopy

Table 3.12: Chemical "hifts of protons on Heteroaromatic Ring~


(,~ ~-.'
I

'"

{5::8

6.30

\~

N
H -g.O

./ 7.40

8.77

'0 0
6 99
.
8.50

Iii
~~
6.54

~S/ 7.30

7.50

fJ)634

{- -~7.10

~850

QI

9 24
.

~~

7.37

7.00

,) 9.26

6.67r,-----;- 7.32

II

7.78~

Ii
.>--CHO
9.70

Q !I

6.3 0f1

6.63f--f1--~COOCH 3

7.17
7 . 2 4 V 7.83

6.98

--CHO
9.45
H-Il.l

6.57r~--COOCH3

6.lrIl 6.

6.76Y 7.44

6.92y-~ COCH3

CH33.92

7.22

77

r:-- ):,7.78
I.

7.78~

Table 3.13, Chem',a' Sh'fts .f "COO(},

GO
I

9.92

"C~N, (al,.

RCH=O
PhCH=O

9.70

RCH=CHCH=O

9.78

9.98

"+0 )
o

Proton'

80

Spectroscopic Data Chemistry

8.05
8.05

HCOOR
HCONR2

RCB=NOH cis

5.00
7.25

RCB = NOH trans

6.65

RCH~N-NH~NO,

6.05

HC(OR)3

N02

3.5: Protons on Heteroatoms


Table 3.14: Protons subject to Hydrogen. Bonding Effects (protons on
Heteroatoms)"
Proton

Class

OH

Carboxylic acids
Sulfonic acids
Phenols
Phenols (intramolecular

-13.2--10.0
12.0-10.0
-7.5--4.0
12.5-5.5

H bond)
Alcohols
InDMSO
Enols (cyclic ( l - diketones)
Enols ( (3- diketones)
Enols ( (3- ketoesters)
Water (Bulk water

4.0--0.5
6.2-4.2
6.9-6.0
16.5-14.5
10.6--9.6
5.0-4.5

as suspended droplets or
wall films)
Dissolved (monomeric)

1.5

Water
in acetone
inDMSO
Oximes

2.9-2.5
3.4--3.2
12.0-9.0

81

Proton Magnetic Resonance Spectroscopy

Proton

NH2 and NHR

Class

Alkyl and cyclic

3.0-0.5

amines
Aryl amines
Amides
Urethanes
Amines in tritluoroacetic acid
SH

Aliphatic mercaptans
Thiophenols

5.0-3.0
8.7-5.0
7.6-4.6
8.7-6.0
1.7-1.3
3.6-2.8

Solvent CDCI 3 Chemical shifts within a range are a function of concentration


(The upper limit represents neat liquids, the lower limit, dilute solutions or
extrapolations to infinite dilution)

3.6: Proton Spin Coupling Constants


Type

Jab (Hz)

Jab Typical

0-30

12-15

6-8

0-1

6-14
0-5
0-5

8-10

Geminal

Vicinal
CH. - CHb (free rotation)

I
I

CH - (-C-) -CH

Ha

ax-ax
ax--eq
eq--eq

2-3
2-3

Spectroscopic Data Chemistry

82

o::.H'
ITHa

cis 5-10

Hb

(cis or trans)

trans 5-10
cis 4-12

Hb
trans 2-10

(cis or trans)

cis 7-13
Hb

(cis or trans)

trans 4-9
4-10

1-3

2-3

5-8

12-18

17

)c=c<:

0-3

0-2

Ha>C=C<Hb

6-12

10

>C=C<

0-3

1-2

> C=C<CHa
Hb

4-10

CH.-OHb (no exchange)


0

II
>CH.-CHb
0

II
C=CHa-CHb
Ha)c=e<Hb

CHa

CHb

83

Proton Magnetic Resonance Spectroscopy


CHb

)C=C<
Ha

C=CHa-CHb=C
Ha,
)1b
C=C
(ring)

HaC=CHb

0-3

1.5

0-3

9-13

10

3 member

0.5-2.0

4 member

2.5-4.0

5 member

5.1-7.0

6 member

8.8-11.0

7 member

9-13

8 member

10-13

9.5-9.8

9.1

CHa-C=CHb

2-3

-CHa-C=C-CHb

2-3

Ha

Hb~

Ha~Hb

Ha~
Ha

&Hb

Hb

2.5

J (ortho)

6-\0

J (meta)

1-3

J (para)

0-1

-0

J (2-3)

J (3-4)

5-6
7-9

J (2-4)

1-2

1.5

J (3-5)

1-2

1.5

J (2-5)

0-1

J (2--6)

0-\

-0

Spectroscopic Data Chemistry

84

40'
:0:
:0:
5

1.3-2.0

1.8

J (3-4)

3.1-3.8

J (2-4)
J (2-5)

0-1
1-2

3.6
-0

J (2-3)

4.9-6.2

5.4

J (3-4)

3.4-5.0

4.0

J (2-4)

1.2-1.7

J (2-5)

3.2-3.7

1.5
3.4

J (1-2)

2-3
2-3
2-3

J (1-3)
J (2-3)
J (3-4)
J (2-5)

3-4
1-2
1.5-2.5

J (4-5)

4-6

J (2-5)

1-2
0-1
2-3

J (2-4)

50
4

6::--"""

J (2-3)

J (2-4)

J (4-6)
J (4-5)

:(Jt

J (2-5)

3-4
1-2

J (2-4)

-0

CH3 -CH 2 -X

6.5-7.5

CH3 > CH-X


CH3

5.5-7.0

1.5

Proton Fluorine

>C<H

Fb

44-81

85

Proton Magnetic Resonance Spectroscopy

I
>CHa-CFb

3-25

> CHa-C-CFb
II

0--4

I 1
Ha

>C-C<

Ha

1-8
Fb

<
>C=C

12-40

Fb

0--6-10

o-Ha

m-5-6
p-2

Proton Phosphorus
0

II
630-707

>PH
(CH3)3 P

2.7

(CH 3)l=O

13.4

(CH3CH2)l

13.7 (HCCP)

0.5 (HCP)

(CH3C~)3

16.3 (HCCP)

11.9 (HCP)

P=O

II
CHl(OR)2

10-13

I II

CH3C P(OR)2

15-20

CHPP(OR)2

10.5-12

P[N(CH3)2]3
o=p [N(CH3)2]3

8.8
9.5

86

Spectroscopic Data Chemistry

3.7: Chemical Shifts, Multiplicities, and Coupling Constants of


Residual Protons in Commercially Available Deuterated Solvents
Compound"
Molecular Weight

0H (mult)

Acetic acid. d4

11.53(1)

64.078

2.03 (5)

Acetone - d6

2.04(5)

2.2

1.93 (5)

2.5

64.117
Acetonitrile - d3
44.071
Benzene - d6

7.15 (br)

84.152
Chloroform - d

7.24(1)

120.384
Cyclohexane - d l2

1.38 (br)

96.236
Deuterium oxide
20.028

4.63
(DSS)b
4.67
(TSP)b

1,2 - Dichloroethane-d4

3.72 (br)

102.985
Diethyl-d 1O ether

3.34 (m)

84.185

1.07 (m)

Diglyme -d 14

3.49 (br)

148.263

3.40 (br)
3.22 (5)

N, N -Dimethylformamide -d7
80.138
Dimethyl - d6 sulphoxide
84.170

1.5

8.01 (br)
2.91 (5)

2.74 (5)

2.49 (5)

1.7

87

Proton Magnetic Resonance Spectroscopy


p-Dioxane - ds

3.53 (m)

96.156
Ethyl alcohol-d 6 (anh)

5.19 (I)

52.106

3.55 (br)
1.11 (m)

Glyme - d,o

3.40(m)

100.184

3.22(5)

Hexafluoroacetone

5.26 (1)

1.6

deuterate, 198.067
HMPT-d,s

2.53 (2 x 5)

2(9.5)

4.78(1 )36.067

3.30(5)

197.314
Methyl alcohol - d4
Methylene chloride -d 2

5.32(3)

86.945
Nitrobenzene -<-d 5

8.11 (br)

128.143

7.67 (br)
7.50 (br)

Nitromethane -do,

4.33 (5)

64.059
5.12(1)

Isopropyl alcohol -ds


68.146

3.89 (br)

Pyridine - d5

8.71 (br)

84.133

7.55 (br)

I. 10 (br)

7.19 (br)
Tetrahydrofuran - ds
80.157

3.58 (br)

Toluene- ds

7.09 (m)

100.191

7.00 (br)

1.73 (br)

6.98 (m)
2.09(5)
Trifluoroacetic acid -d
115.030

11.50(1 )

? ..,

_.,)

1.7

Spectroscopic Data Chemistry

88
2,2,2-Trifluoroethyl
alcohol- d,,

3.88 (4

103.059
a
b

5.02(1)
x

3)

2(9)

Purity (Atom % D) up to 99.96% (" 100%") for several solvents.


DSS is 3-(trimethylsilyl}-l-propane sulfonic acid, sodium salt (or sodium
2,2-dimethyl-2-silapentane-5-sulfonate). TSP is sodium -3trimethylpropionate -2, 2, 3, 3-d4 . Both are reference standards used in
aqueous solutions.

NMR table showing correlations of chemical shifts of protons


Type and group

't

10.00
9.78
8.92-9.12

0.22
1.08--0.88

2.

TMS
-CH 2-Cyclopropane

3.
4.

CK-CN
J
CH 3-C-(sat.)

9.05-9.15

0.95--0.85

(8.7-9.3)
8.88-9.07

(1.3--0.7)

I.

5.

CK-C-CO-R
J

6.

CH 3-C-N-CO-R

8.80

7.

-N-C-

8.52

1.20
1.48

8.

CH 2
-CH 2- (sat.)
-CH 2- C-O-COR and

8.52-8.80

1.48-1.20

8.50

1.50

9.

\/

1.12--O.93

-CH 2-C-O-Ar
10.

RSH,

8.5-8.9"

1.5-1.1

11.

RNH2 (conc. less than

8.5-8.9"

1.5-1.1

I mole in inert solvent)


12.

-CH2-C-C=C-

8.40-8.82

1.60-1.18

13.

-CH 2-CN

8.38-8.80

1.62-1.20

14.

-C-H (sat.)

8.35-8.60

1.65-1.40

15.

8.22-8.40

1.78-1.60

16.

-CH2-C-Ar
-CH 2-C-O-R

8.19-8.79

1.81-1.21

17.

CH,-C=NOH
,

8.19

1.81

18.

-CHz-C-1

8.14-8.35

1.86-1.65

89

Proton Magnetic Resonance Spectroscopy

8.10-8.40

1.91.4

CH 3-C=C

8.1-8.4

L9-1.4

CH -C=C3I

8.09-8.13

1.91-1.87

19.

-CHz-C-COR

20.
21.

O-CO-R

22.

-CH z-C=C -O-R

8.07

1.93

23.

-CH 2-C-CI

8.04-8.40

1.96-1.60

24.

CH -C=C3 I

7.97-8.06

2.03-1.94

COOR orCN

25.

-cH2-C-Br

7.97-8.32

2.03-1.68

26.

CH 3-C=C-C0-R

7.94-8.07

2.06-1.93

27.

-CH 2--C-N0 2

7.93

2.07

28.

-CH 2-C-SO z-R


-C-O

7.84

2.16

7.71

2.29

29.

\/

CH

30.

-CH 2-C=C

7.69-8.17

2.31- 1.83

31.

CH 3-N-N-

7.67

2.33

32.

-CH 2-CO-R

33.

CH3-S0-R

34.

CH,-Ar
,

7.61-7.98

2.39-2.02

7.50

2.5

7.50-7.75

2.50--2.25

(7.5-7.9)

(2.5-2.1 )

35.

-CHz-S-R

7.47-7.61

2.53-2.39

36.

CH3-C0-SR
-CH 2-C=N

7.46-7.67

2.54-2.33

37.

7.42

2.58

38.

CH 3-C=0

7.4-7.9

2.6--2.1

(7.4-8.1)

(2.6-1.9)

39.
40.

CH 3-S-C=N
CH3-CO-C = C or

7.37

2.63

7.32-8.17

2.68-1.83

CH 3-C0-Ar

41.

CH,-CO-CI
or Br
,

7.19-7.34

2.81-2.66

42.

CH,-S,

7.2-7.9

2.8--2.1

43.

CH,-N
,

7.0-7.9

3.0-2.1

44.

-C=C-C=C-H

7.13

2.87

Spectroscopic Data Chemistry

90
45.
46.
47.
48.
49.
50.
51.
52.
53.
54.
55.
56.
57.
58.
59.
60.
61.
62.
63.
64.
65.
66.
67.

-CHz-SOz-R
-C=C-H, nonconjugated
-C=C-H, conjugated
Ar-C=C-H
-CH/C=C-)z
-CHz-Ar
-CH 2-1
-CHz-SOl
Ar-CHz-N
-CHz-N-Ar
Ar-CHz-C=C-CHz-N+-CHz-CI
-CHz-O-R
CH 3-O-CHz-Br
CH 3-O-SO-OR
-CHz-N=C=S
CH 3-SO z-CI
Br-CHz-C=N
-C=C-CHz-Br
Ar-CHz-Ar
Ar-NH az' Ar-NH-Ra,
and Ar-NH-Ar"

68.
69.
70.
71.
72.
73.
74.
75.

CH 3-O-SO z-OR
-C=C-CHz-O-R
-C=C-CHz-C1
CI-CHz-C=N
Hz-C=C-O-CHz-C=C
~C=C-CHz-CI

-C=C-CHz-OR
-CHz-O-CO-R or
-CH1-O-Ar

7.08
7.35-7.55
6.9-7.2
6.95
6.95-7.10
6.94-7.47
6.80-6.97
6.72
6.68
6.63-6.72
6.62-6.82
6.60
6.43-6.65
6.42-7.69
6.2-6.5
(6.0-6.7)
6.42-6.75
6.42
6.39
6.36
6.30
6.18
6.08-6.19
6.0-6.6
(5.7-6.7)
6.06
6.03-6.10
5.96-6.04
5.93
5.87-6.17
5.84-5.91
5.82
5.71-6.02

2.92
2.65-2.45
3.1-2.8
3,05
3.05-2.9
3.06-2.53
3.2-3.D3

3.28
3.32
3.37-3.28
3.38-3.18
3.40
3.57-3.35
3.58-2.31
3.8-3.5
(4.0-3.3)
3.58-3.25
3.58
3.61
3.64
3.70
3.82
3.92-3.81
4.0-3,4
(4.3-3.3)
3.94
3.97-3.90
4.04-3.96
4.07
4.13-3.83
4.16-4.09
4.18
4.29-3.98

91

Proton Magnetic Resonance Spectroscopy


76.

-CH 2-N01

5.62

4.38

77.

Ar--CH 2-Br

5.57-5,59

4.43-4.41

78.

Ar-CH 2-OR

5.51 -5.64

4.49-4.36

79.

Ar-CH 2-Cl

5.50

4.50

80.

--C=CH 2

5.37

4.63

81.

-C=CH-, acyclic,

4.3-4.9
(4.1-4.9)

5.7-5 '
(5.9-5 I)

4.3-4.8

5.7-5,2

nonconjugated
82.

--C=CH-, Cyclic,
nonconjugated

83.

-C=CH 2

4.3-4.7

5.7-5.3

(3.7S-4.8)

(6.2S-5.2)

4.80-S.20

5.20-4.80

4.74

5.26

84.

--CH(OR)2

85.

Ar--CH 2-O-CO-R

86.

R-O-H (conc. less


4.8-7.0'
than one mole in inert solvent)

87.

Ar-C=CH-

4.60-4.72

S.40-S.28

88.

-CH=C-O-R

4.45-S.46

5.S5-4.S4

89.

-CH=C-C=N

4.25

S.75

90.

--C=CH-CO-R

3.95-4.32

6.05-S.68

91.

R-CO-CH=C-CO--R

3.87-3.97

6.13-6.03

92.

Ar--CH=C-

3.72-3.77

6.28---6.23

93.

--C=C-H, conjugated

3.3-4.5
(2.2-4.7)

(7.8-S.3)

5.2-3.0'

6.7-S.S

94.

--C=C-H, acyclic,
conjugated

3.S--4.0
(2.9-4.5)

6.S---6.0
(7.1-S.S)

95.

H--C = C-

3.60-3.70

6.40-6.30

-C=CH-O-R

3.55-3.78

6.45---6.22

97.

Br--CH=C-

3.00-3.38

7.00-6.62

98.

-CH=C-CO-R

2.96-4.S3

7.04-S.47

99.

-C=Ch-O-CO-CK,

2.7S

7.2S

H CO--R
96.

92

100.

101.

Spectroscopic Data Chemistry

(Jo{

2.6-2.7

7.4-7.3

N
H
R-CO-NH

2.3-3.9

7.7-6.1

(1.5-4.5)

(8.5-5.5)

2.28-2.62

7.72-7.38

2.0-3.4

8.0-6.6

(0.5-4.0)

(9.5~.0)

1.4-3.8

8.6-6.2

(1.0-6.0)

(9.0-4.0)

1.9-2.1

8.1-7.9

1.8-2.0

8.2-8.0

0.32-0.57

9.68-9.43

0.2-0.3

9.8-9.7

(0.2-0.5)

(9.8-9.5)

0.0-0.3

10.0-9.7

(-0.1 to 0.5)

(10.1 to 9.5)

-1.52 to -0.97

11.52to 10.97

-2.0 to -1.0

12.0 to 11.0

-2.18to-1.57

12.18 to 11.57

102.

Ar-CH-C-CO-R

103.

ArH, benzenoid

104.

ArH, nonbenzenoid

~p
105.

H-C", /
N"",

~p
106.

H-C

107.

-C=C-CHO,

"'0-

aliphatic, a, 13 unsat.
108.
109.

R-CHO, aliphatic
Ar-CHO

110.

R-COOH

III.

-SO,H

112.

-C=C-COOH

113.

R-COOH, dimer

-2.2 to -1.0

12.2 to 11.0

114.

AR-OH, intramolecularly

-2.5 to -0.5

12.5 to 10.5

bonded

(-5.5 to -0.5)

(15.5 to 10.5)

115.

AR-OH, polymeric

2.3 to 5.5"

7.7t04.sa

.'

association
116.

Enols

~.O

to -5.0

16.0 to 15.0

93

Proton Magnetic Resonance Spectroscopy

Normally protons resonate within the range shown. In cases in which


protons resonate outside the range, the limits are shown by values in parentheses.
a

The position of these protons depends on concentration, temperature, and


the presence of other exchangeable protons. Values for amino protons depend
on the basicity of the nitrogen atom.

In these compounds R=H, alkyl, aryl, OH, OR or NH 2.

Exercises and Problems:


Problem 1. The compounds CHCI 2--CHCI2 (8=6 ppm) and CCI3-CHFI
(8=3.9 ppm) produce single NMR signals owing to the factthat their hydrogen
atoms are chemically equivalent. Explain the difference between the chemical
shift for these compounds.
Answer: Halogens shift the proton signal downfield and the shift is the
larger, the larger the number of halogen atoms.
Problem 2. Toluene, p--xylene and mesitylene have two peaks each in
their NMR spectra. Assign the spectra shows in fig. shown below (l, 2 and 3)
to these compounds.
Alkyl Aromalic

3:5

HFf ')-cH3

3:2

94

Spectroscopic Data Chemistry

Answer: The signal with 8=2 ppm is produced by the protons of the
methyl group and the signal at about 7 ppm by the aromatic protons. As the
lines have approximately the same width, the ratios of the peak areas are 3:5,
3:2 and 3: I in the first, second and third spectra, respectively. Hence, the spectra
can be assigned as follows: 1. Toluene, 2. (r-xylene, 3. mesitylene.
Problem 3. Identify the structures of the compounds C3HFI5 (I) and
C 3 H5CI 3 (2) with the following NMR spectra:
(I) Triplet (8=4.52 ppm) and doublet (8=6.07 ppm) with the peak area
ratio of 1:2
(2) Singlets (8=2.20 ppm and 8=4.02 ppm) with the peak area ratio of3:2
Answer: The triplet with 8=4.52 ppm and the doublet with 8=6.07 ppm
indicate that the methine group (lH) has a neighbour with two protons (2H).
Hence the compound (I) has the following structure:
H

CI

H-C-C-C-CI

CI CI CI
The singlets in the spectrum ofthe compound (2) indicate that two proton
groups are separated by an aprotic group making spin-spin coupling impossible.
Thus, the compound (2) has the following structure:
H

CI H

H-C-C-C-H

CI CI H
Problem 4. Fig. shown below gives two spectra for the compounds
with the same empirical formula CgHto0' Determine the structure and explain
the differences in the chemical shifts.
Answer: I. C6H5-CH 2-O-CH3
2. C6H5-O-CH2-CH3
In the compound (I) the oxygen atom is linked to the groups CH 2 and
CH 3 and therefore both peaks are shifted downfield (the chemical shifts are
larger) and there is no spin-spin coupling between the protons of these groups.
In the compound (2) the oxygen atom affects the group CH 2 (downfield
shift of the peak) and the group C6HS- The aromatic protons become
nonequivalent and the signal is split into a multiplet owing to their coupling.

95

Proton Magnetic Resonance Spectroscopy

10

Problem 5. Deduce the structure of the compound C 3 H 4 zS

J
7

Integration ration 1: 1:2

Answer:
C,H4 N zS Index = 3
07.08 (1 H) J = 5Hz
doublet
06.48 (1 H) J = 5Hz
doublet
very broad 05.61 (2H) ...
The two non-equivalent protons, which are coupled to each other are in
the aromatic region. With an index value of 3 and only 3C I atoms, only
imidazole and thiazole are the possible aromatic compounds. But the former,
imidazole - thiol has four non-equivalent protons as against three observed.
So the compound is aminothiazole. The J value indicates vicinal positions for
the aromatic and hence the compound is 2-aminothiazole.

~/

rfIllNj~

SH

N
H
Imidazothiol

H2N

~~
S

NH2

2-Aminothiazole
SH

S
5-Aminothiazo Ie

~NON
S
4-Aminothiazole

96

Spectroscopic Data Chemistry


Problem 6. Why is an internal standard used in obtaining an nmr

spectrum? Why is TMS a good standard?


In NMR spectroscopy, we are trying to determine the strength of
magnetic field which is required to bring about the resonance of certain nuclei
in a given compound. It is natural to expect, therefore, that a NMR spectrum
would be a plot of signal strength versus magnetic field, in units of miIIigauss.
Measuring a magnetic field is difficult. However, it is convenient to determine
accurately the values of absorption frequencies (.: u = yHo/2n) of protons
relative to those of a suitable standard. As only relative absorption values can
be obtained, a suitable standard must be used.
The most logical standard would be a "bare proton", having no shielding
electrons, but experimentally this is not possible, and instead one uses as
standards compounds having sharp resonance peaks. The chemical shift may
then be expressed as the difference between the resonance frequency of the
protons in the sample (u sampe
I) and the resonance frequency of the protons in
the standard

(ustandard)

(u sample -

U TMS )

TetramethylsiIane (TMS) is commonly used as an internal reference


TMS is a good standard because
(i) TMS is unreactive (except with con. H2 S04 with which it should
not be used) and it does not associate with the sample.
(ii) TMS is symmetrical, and thus gives a sharp peak of 12 equivalent
protons.
(iii) It is extremely volatile, and thus allows recovery of the pure sample.
(iv) It is soluble in most organic solvents. Methyl protons ofTMS are
strongly shielded and therefore absorbs at higher field than almost
all organic protons.
It also enables us to define a scale for the spectra by arbitrarily
assigning a frequency value for TMS protons equal to zero.
Problem 7. Which references and solvents are used to take NMR spectra
of samples? Why?
I,

Proton Magnetic Resonance Spectroscopy

97

To determine the resonance spectrum of the protons of an organic


compound, one needs anywhere betweer. I and about 30 mg of the sample.
The sample is normally used in the form of its dilute solution (about 2 to \0%)
in a solvent which contains no hydrogen atoms of its own.
For samples oflow polarity, carbon tetrachloride, deuterated chloroform,
CDCl 3 and deuterated benzene C6D6 , are often used. On the other hand if the
sample is soluble only in polar solvents, deuterium oxide (0 2), acetone - 0 6
(CD 3COCD3), or dimethyl sulfoxide -- 0 6 [(CD3)2S0l are often employed.
The internal standard used to locate the resonance frequency of most
protons is tetramethyl silane (TMS) [(CH3)4 Sil, which one adds to the sample
before recording the spectrum. TMS is commonly used as an internal reference
because it is chemically inert, symmetrical, volatile and soluble in most organic
solvents, it gives a single sharp absorption peak and absorbs at higher field
than almost all organic protons.
TMS cannot be used as an internal reference for substances dissolved
in

DzO. For aqueous solutions, the standard used is often the sodium salt of

2,2-dimethyl-2-silapentane-5-sulfonic acid or DSS.


(CH 3)3 SiCH2CH zCH zS03Na
The methyl groups in this compound provide a suitable reference peak.
Acetonitrile and dioxane are also used as references in aqueous solution.
Problem 8. Explain the abnormally large shift of aldehydic proton in

nmr spectra.
If molecules contain protons that are sterically oriented so that they are
close to double or triple bonded groups, there will generally be a diamagnetic
anisotropic effect of some kind.
The magnetic fields induced by pi electrons are directional, i.e.,
unsymmetrical. A measurement which varies with the direction in which the
measurement is taken is said to be anisotropic. Because the effects of molecular
fields induced by 1t electrons are direction dependent, these are, therefore termed
anisotropic effects. These effects are contrasted to inductive effects, which are
symmetrical around the proton.

98

Spectroscopic Data Chemistry

/"7f-//I~::,j,

-- ''r\t:P

1/ , I
~ C;:=lO

/k.

Induced magnetic field

~
~;i
-- ~' "fr--

',H

Ho
applied magnetic field
Anisotropic effects occur in addition to the ever present molecular field,
induced by sigma-bond electrons.
Thus the downfield shift of aldehyde proton (8 9- I 0) is not only due to
the deshielding effect of Sp2 carbon (Sp2 carbon has high s character and
withdraws electrons, deshielding the hydrogen) but also due to anisotropy of
the C=O. These two effects combined together deshield the attached hydrogens
in these systems.
Just like in benzene, in aldehyde, the induced magnetic field (by the
1t--electrons) in the region where protons are located is oriented in the same
direction as the applied field. A smaller field is therefore, required for resonance
resulting in their deshielding. "The highly deshielded position of aldehydes is
attributed to a combination of a strong inductive effect and the diamagnetic
anisotropy of the carbonyl group."

aaa

13e NMR Spectroscopy


4.1: The 13C chemical shifts of Linear and Branched Alkanes:
Alkane groups unsubstituted by heteroatoms absorb downfield from
TMS to about 60 ppm. (Methane absorbs at 2.5 ppm upfield from TMS.)
Within this range we can predict the chemical shifts of individual 13C atoms in
a straight chain or branched chain hydrocarbon from the data in Table 4.1 and
the formula b = -2.5 + LnA.
Where b = Predicted shift for a carbon atom.
A = Additive shift parameter.
n = number of carbon atoms for each shift parameter (-2.5 is the shift
of the i3C of methane).
The calculated (and observed) shifts for the carbon atoms of
3-methylpentane are

/+ 19.3 (18.6)

CH 3
I
I

CH 3 -

+ 11.3
(+11.3)

CH 2 -

CH- CH 2 -

+29.5
(+29.3)

"

+ 36.2
(+ 36.7)

CH 3

100

Spectroscopic Data Chemistry


For carbon atom I, we have la,

=-2.5 + (9.1
1

I) + (9.4

I~-,

2y and 1&-carbon atoms.

I) + (-2.5

2) + (0.3

I)

+ 11.3

Carbon atom 2 has 2 a-, 2 ~-, and 1 y carbon atoms. Carbon atom 2 is
a 2 carbon with a 3 carbon attached [2(3) = - 2.5]

=-2.5 + (9.1 x 2) + (9.4 x 2) + (-2.5 x 1) + (-2.5 x 1) = 29.5

Carbon atom 3 has 3 a- and 2 ~- carbon atoms, and it is a 3 atom with


two 2 atoms attached [3 (2) = -3.7]. Thus 03 = -2.5 + (9.1

+ (-3.7

3) + (9.4 x 2)

2) = + 36.2

Carbon atom 6 has, I a-, 2~-, and 2y carbon atoms, and it is a 1 atom
with a3 atom attached [10 (3) =-1.1]. Thus,
+(-2.5x2)+(-1.l

=-2.5 +(9.1 x 1)+(9.4 x 2)


6

1)=+19.3

The agreement for such calculations is very good. It is essential that the
reference compounds used for such additivity culculations be structurally similar
to thecompound of interest.
Table 4.1: The \3C shift parameters in some linear and branched
hydrocarbons
13C

Atoms

Shift (ppm) (A)

+9.1

+9.4

Y
b

-2.5

+0.1

+0.3

1 (3?

-1.1

1 (4)"
20 (3 o)a

-3.4

20 (4)

-7.2

3 (2)

-3.7

3 (3)

-9.5

4 (10)

-1.5

4 (2)

-8.4

-2.5

101

I3C NMR Spectroscopy


a

The notations 1 (3) and 1 (4) denote a CH 3 group bound to a R2CH


group and to a R3C group, respectively. The notation 2 (3) denotes a RCH 2
group bound to a ~CH group, and so on.

Table 4.2 lists the shifts in some linear and branched alkanes.
Table 4.2: The \3C Shifts for some Linear and Branched chian Alkanes
(ppm from TMS).
Compound

C-l

C-2

C-3

Methane

-2.3

Ethane

5.7

Propane

15.8

16.3

15.8

Butane

13.4

25.2

25.2

Pentane

13.9

22.8

Hexane

14.1

Heptane

C-4

C-5

34.7

22.8

13.9

23.1

32.2

32,2

23.1

14.1

23.2

32.6

29.7

32.6

Octane

14.2

23.2

32.6

29.9

29.9

Nonane

14.2

23.3

32.6

30.0

30.3

Decane

14.2

-23.2

32.6

31.1

30.5

Isobutane

24.5

25.4

Isopentane

22.2

31.1

32.0

11.7

lsohexane

22.7

28.0

42.0

20.9

Neopentane

31.7

28.1

2,2-Dimethylbutane

29.1

30.6

36.9

8.9

3-Methylpentane

11.5

29.5

36.9

(18.8,3CH)

2,3-Dimethylbutane

19.5

34.3

2,2,3-Trimethyl

27.4

33.1

38.3

16.1

7.0

25.3

36.3

(14.6,3-CH 3)

butane
2,3-Dimethylpentane

14.3

102

Spectroscopic Data Chemistry

Table 4.3: Incremental Substituent Effects (ppm) on Replacement ofH by


Y in Alkanes. Y is Terminal or Internal" (+ downfield, -upfield)
y

...

~y'"
~

Terminal
Y

Internal
~

Terminal
Internal
Terminal
Internal
+9
+6
+10
+8
-2
CH3
CH=CH2
+20
+6
-0.5
+4.5
+5.5
-3.5
C=CH
+2
COOH
+21
+16
+3
-2
COO-2
+25
+20
+5
+3
+2
-2
COOR
+20
+17
+3
+33
+28
+2
COCI
+22
CONH2
-0.5
+2.5
+30
+24
+1
+1
-2
COR
-2
CHO
+31
0
Phenyl
+23
+17
+9
+7
-2
+48
+41
+10
+8
-5
OH
+58
+51
+8
+5
-4
OR
+51
+45
+6
+5
-3
OCOR
-5
+29
+24
+11
+10
NH2
-5
NH3+
+26
+24
+8
+6
+8
+6
-4
NHR
+37
+31
+42
-3
N~
-7
+31
+5
NR/
+4
+4
N0 2
+63
+57
+3
-3
+4
+1
+3
CN
+11
+11
+12
+11
-4
SH
-3
+20
+7
SR
-F
+6
-4
+9
+68
+63
+31
+32
+11
+10
-4
CI
+ 11
+20
+10
-3
Br
+25
-1
+4
+11
+12
I
-6
a Add these increments to the shift values ofthe appropriate carbon atom in
Table 4.2 or to the shift value calculated from Table 4.1.
From Table 4.3, the approximate shifts for the carbon atoms of, for example,
3-pentanol, may be calculated from the values for pentane in Table 4.2; that

I1C NMR Spectroscopy

103

is, the increment for the functional group in Table 4.3 is added to the appropriate
value in Table 4.2 as follows:
y

f3

CH 3 -

CH 2 -

CH- CH 2 I

f3

CH 3

OH

Ca

CI3
Cy

Calculated

Found

34.7 + 41 = 75.8
22.8 + 8 = 30.8
13.9 - 5 = 8.9

73.8
30.0
10.1

The chemical shifts of the CH 2 groups in monocyclic alkanes are given in


Table 4.4. Each ring skeleton has its own set of shfit parameters. Rough estimates
for substituted rings can be made with the substitution increments in Table 4.3.
Table 4.5 presents chemical shifts for several saturated heterocyclics.

Table 4.4: Chemical shifts of Cycloalkanes (ppm from TMS)

C3 H6
C4HS
CsHIO
C6 HI2
C7H I4
CgH I6
CgH 1S
C 1oH20

-2.9
22.4
25.6
26.9
28.4
26.9
26.1
25.3

Table 4.5: Chemical shifts for saturated Heterocyclics (ppm from TMS,
neat) Unsubstituted

29.7

H
N

39 .5

27.5

18 .7

65

12

68.4

31.7

0 0
S

18 .2

22.9

0
N
H

72.6

57
47.1

104

Spectroscopic Data Chemistry


24.9

26.6

0
o

27.7

/' 69.5

25.9

27.8
29.1

N
H

Substituted

~CH3

47.3 /

47.6

27.8
47.9

24.4
567

CH3
48.0

18.1

4.2 Alkenes and Alkynes


The Sp2 carbon atoms of alkenes substituted only by alkyl groups, absorb
in the range of about 11 0-150 ppm downfield from TMS. The double bond
has a rather small effect on the shift of the Sp3 carbon in the molecule. Calculation
of approximate shifts can be made from the following parameters where (a, ~,
and y represent substituents on the same end of the double bond as the alkene
carbon of interest, and (a', W, and y' represent substituents on the far side.
a
+10.6
~
+7.2
Y
-1.5
a'
-7.9
~'
-1.8
y'
-1.5
Z (cis) correction
-1.1
These parameters are added to 123.3 ppm, the shift for ethylene. We can
calculate the values for cis-3-methyl-2-pentene as follows:
a

CH3H

P a
H3 C-CH 2 5

0C_3

C = C -CH3
3

= 123.3 + (2 x 10.6) + (l x 7.2) + (l x -7.9) - 1.1

= 142.7 ppm.

a'

CH3H
W a'
H,C-CH 2 Os

0C_2 =

123.3 + (I

-<

C =C
3

-cI H3

10.6) + (2 x -7.9) + (I x 1.8) -- l.l

115.2 ppm.

The measured values are C-3 = 137.2 and C-2 = 116.8. The agreement
is fair. The allylic carbon of a (Z) alkene is usually at lower field from that of

IlC NMR Spectroscopy

lOS

an (E) alkene by about 4-6 ppm. Alkene carbon atoms in polyenes are treated
as though they were alkane carbon substituents on one of the double bonds.
Thus in calculating the shift ofC-2 in I A-pentadiene, C-4 is treated like a 13spJ carbon atom.
Representative alkenes are presented in Table 4.6.
There are no simple rules to handle polar substituents on an alkene carbon.
Shifts for several substituted alkenes are presented in Table 4.7.
The central carbon atom (=C=) of alkyl substituted allenes absorbs far
downfield in the range of about 200-215 ppm, whereas the terminal atoms
(C=C=C) absorb upfield in the range of about 75-97 ppm.

Table 4.6: Alkene and Cycloalkene Chemical shifts (ppm from TMS)
111 ,

H2C=CH~

Iic/C~""'Gr~Ci:i2

I".'

IHJ .1

11-11

H,C "cH(CI~"at~CH,
"XI

, .?_~ 7

1175

t~C"

~rn
1112

~,

CH,
-

Spectroscopic Data Chemistry

106

J 14 ~

I ~') .:;

HF, /GI~
ill
"CH-CH 1
1.17 M

13-' 2

121\.l

127A 123 I

J .125

172

12 H

IIW.

H2C, /CH,,,,,- /C~


C
CH:
1';15 I
CIt

.'

CH,
I .

1129

H~C~I/GI"'-cI-~CH3
1.;49

107.1
CH2

/~.7

130.8

3 0 . 2 0 137.2

0-',-6
22.1

:-

0
I

6. 1

124.6

22.3

CH,=C=CH,
74 X

:: I ~ "

136 .2

~--./)2g.9
26.9

107

IlC NMR Spectroscopy

Table 4.7: Chemical Shifts of substituted Alkenes (ppm from TMS)


1220

I~C.-;7

12f1 I

or,

a-I,

I~C~

'Br

11<0

l:1

117 -I

141 7

136 -'

~rn" 1~70

H,C9'
%

I.~X :\

~~O-I~o

OCCR

11101 '

l."th ()

11.)1 I

o
I ~~"

H,C~aI" C':CH, H,C~ "COOH


11Y ~

II

I.' i"

o
1077

f-l,~rn"CN
1~7K

144 I

117~

o
A,133.8

L~165.1

1 he sp carbon atoms of alkynes substituted only by alkyl groups absorb in the


range of approximately 65--90 ppm (Table 4.8). The triple bond shifts the Sp3
carbon atoms directly attached about 5-15 ppm upfield relative to the
absorbs upfield from the internal
corresponding alkane. The terminal",
",CR. Alkyne carbon atoms with a polar group directly attached absorb from
about 20-95 ppm.

CH

108

Spectroscopic Data Chemistry

Table 4.8: Alkyne Chemical Shifts (ppm)


Compound
I-Butyne
2-Butyne
I-Hexyne
2-Hexyne
3-Hexyne

C-I
67.0
67.4
1.7
14.4

C-2
84.7
73.6
82.8
73.7
12.0

23.2 894

C-3

C-4

C-5

C-6

17.4
76.9
79.9

29.9
19.6

21.2
21.6

12.9
12.1

280 88.4

HC=C-OCH 2CH 3

CH 3-C=C-OCH3

4.3: Aromatic Compounds


Benzene carbon atoms absorb at 128.5 ppm, neat or as a solution in
CDCI 3 or CCI4 Substituents shift the attached aromatic carbon atom as much
as 35 ppm.
Fused ring absorptions are as follows:
Naphthalene: C-I, 128.1; C-2, 125.9; C-4a, 133.7
Anthracene: C-I, 130.1; C-2, 125.4; C-4a, 132.2; C-9, 132.6
Phenanthrene: C-l, 128.3; C-2, 126.3; C-3, 126.3; C-4, 122.2; C-4a, 131.9*;
C-9, 126.6; C-lOa, 130.1 *.
Incremental shifts from benzene for the aromatic carbon atoms of
representative monosubstituted benzene rings (and shifts from TMS of carbon
containing substituents) are given in Table 5.9.
*Assignment uncertain.
Table 4.9: Incremental shifts ofthe Aromatic Carbon Atoms of Monosubstituted Benzenes (ppm from Benzene at 128.5 ppm, +downrreld, upfield). Carbon Atom of substituents in parts per million from TMS
Substituent

H
CH 3
CHFH3
CH(CH3)2
qCH 3)3
CH=CH 2
C=CH
C6HS
CHzOH

C-l
(Attachment)

C-2

C-3

C-4

0.0
9.3
+15.6
+20.1
+22.2
+9.1
-5.8
+12.1
+13.3

0.0
+0.7
-{).5
-2.0
-3.4
-2.4
+6.9
-1.8
-{).8

0.0
-{).l
0.0
0.0
-0.4
+0.2
+0.1

0.0
-2.9
-2.6
-2.5
-3.1
-{).5
+0.4
-1.6
-{).4

-{).I
-{).6

C 1 of substituents
(ppm from TMS)

21.3
29.2(CH 2), 15.8(CH)
34.4(CH),24.1(CH 3)
34.5(C), 31.4(CH3).
137.1(CH), 113.2(CH2)
84.0(C),77.8(CH)
64.5

109

IJC NMR Spectroscopy

20.7(CH 3),66.I(CH).
170.5 (C=O)

+7.7

-0.0

-0.0

-0.0

OH
OCH 3
OC6HS
0

+26.6
+31.4
+29.0

-12.7
-14.4
-9.4

+1.6
+1.0
+1.6

-7.3
-7.7
-5.3

54.1

OCCH 3
0

+22.4

-7.1

-0.4

-3.2

23.9(CH3 ), 169.7 (C=O)

CH
0

+8.2

+1.2

+0.6

+5.8

192.0

CCH 3
0

+7.8

-0.4

-0.4

+2.8

24.6(CH3), 19S.7 (C=O)

CC6HS
0

+9.1

+I.S

-0.2

+3.8

196.4 (C=O)

CCF3
0

-S.6

+1.8

+0.7

+6.7

COH
0

+2.9

+1.3

+0.4

+4.3

168.0

COCH 3
0

+2.0

+1.2

-0.1

+4.8

SI.0(CH), 166.8 (C=O)

CCI
C=N
NH2
N(CH 3)2
0

+4.6
-16.0
+19.2
+22.4

+2.9
+3.6
-12.4
-IS.7

+0.6
+0.6
+1.3
+0.8

+7.0
+4.3
-9.5
-11.8

NHCCH 3
N0 2
N=C=O

+11.1
+19.6
+S.7
+3S.1
+6.4
-S.4
-32.2
+2.6
+2.3
+10.2

-9.9
-S.3
-3.6
-14.3
+0.2
+3.4
+9.9
-3.1
+0.6
-1.8

+0.2
+0.9
+1.2
+0.9
+1.0
+2.2
+2.6
+0.4
+0.2
+0.4

-S.6
+6.0
-2.8
-4.5
-2.0
-1.0
-7.3
+3.4
-3.3
-3.6

CHPC-CH 3

II

II

II

II
II
II
II

II

II

II

F
CI
Br
1
CF3
SH
SCH3

168.S
119.5
40.3

129.S

15.9

110

Spectroscopic Data Chemistry

+15.3
+13.4

SO~NH2

Si(CH))

-2.9
+4.4

+-0.4
-1.1

+3.3
-1.1

Shifts from benzene for polysubstituted benzene ring carbon atoms can
,be approximated by applying the principle of substituent additivity. For
example, the shift from benzene for C-2. of the disubstituted compound 4-chlorobenzonitrile is calculated by adding the effect for an ortho CN group
(+3.6) to that for a meta CI group (+ 1.3):

CN

CN

II

2
3

is equivalent to

CI
I

rAlr(Y 2

~3

II

CAtom Calculated Observed


I
-18.0
-16.6
2
+4.6
+5.1
+0.8
+1.3
3
4
+10.7
+10.8

CAtom Observed
I
-16.0
2
+3.6
+0,6
3
4
+4.3

CI
III
CAtom Observed
-2.0
4
+ 1.0
3
+0.2
2
+6.4
I

Table 4.10: Shift for Carbon Atoms ofHeteroaromatics (neat, ppm from TMS)
C-3 C-4 C-5
109.6
106.2 110.9 141.2
121.7 112.9 148.5
117.9 II 1.9 146.4

C~

Compound
Furan
2-Methyl furan
Furan-2-Carboxaldehyde
Methyl 2-furoate

C-2
142.7
152.2
1533
144.8

Pyrrole
2-Methyl pyrrole
Pyrrole-2Carboxaldehyde
Thiophene
2-Methylthiophene
Thiophene-2Carboxaldehyde
Thiazole
Imidazole
Pyrazole
I-Methylpyrazole
Pyridine
Pyrimidine

118.4 108.0
127.2 105.9 108.1 116.7

12.4

134.0 123.0 112.0 129.0


124.4 126.2
139.0 124.7 126.4 122.6

14.8

143.3 136.4 128.1 134.6


142.4 118.5
152.2
136.2
122.3 122.3
134.3 105.2
139.2 105.7 128.7
150.2 123.9 135.9
157.4 122.1 157.4
159.5

Substituent
13.4
178.2
159.1 (C=O),
51.8 (CH)

182.8

38.1

I3C NMR Spectroscopy

111

Pyrazine
2-Methylpyrazine
Pyridazine
a Assignment not certain

145.6
154.0 141.8" 143.8" 144.701
152.8 127.6

21.6

4.4: Alcohols
Substitution ofH in an alkane by an OH group causes down field shifts
of35-52 ppm for C-I, 5-12 ppm for C-2, and upfield shift of about O-{) ppm
for C-3. Shifts for several acyclic and alicyclic alcohols are given in Table 4.11.

Table 4.11: Chemical shifts of Alcohols (neat, ppm from TMS)


~.' h

H,C;~ /CI-~"'-

CHpH

CH 2

490

OH

25K

~5

H,C ......... ~CHJ


. ~,~ CH
1

OH

OH

19 1

1\7 ()

29.7

OH

OH

1~.O

39 4

)0.)

H1C'c~CH~~,Cl\
194

72)1

OH

~9

112

Spectroscopic Data Chemistry

]1"1\)

(,1"

Hr"

/01'--.,

OH

iOKCR

CH,
2~j

..JJ "

HiC, ...--c~,
./OH
GI
CH,./
00 ~ -

2HI

CHJ
OH
Ih I

72 0

H,C, / G I "
J51 GI
CHJ
I

I~ 7

CH3

(-2

25.9

24.4

35.5

5.0
.4

73.3
OH

69.5

OH

4.5 Ethers, Acetals, and Epoxides :


Table 4.12 Chemical shifts of Ethers, Acetals. and Epoxidcs (ppm from Tms)

52"

H,C,

]jJ

..,.-/~

Cf~
~q

i3C NMR Spectroscopy

113

406

l}'l

//C~
o
6~~)

I
\

""erG

H2C

2h

(1"

CH ')
/ -

(1

151

o
Y'!h /

H~C--

---

CH2---

CH~

CH

. I'IY"

" 0 --

CH
hO 7

2--..... C'li
r 3

4.6: Halides
Table 4.13: Shift Positions for Alkyl Halides (neat, ppm from TMS)
Compound
C-l
C-2
C-3
CH 4
-2.3
CHl
75.4
CH 3CI
24.9
CH,CI,
54.0
CHCI 377.5
CCll
96.5

114
CH3Br
CH 2 Br2
CHBr)
CBr4
CHJ
>
CH}2
CHI,>
CI 4
CH)CHl
CH)CH 2Cl
CH)CH2Br
CH)CH2I
CH)CH 2CH 2Cl
CH)CH 2CH2 Br
CH)CH 2 CH 21

Spectroscopic Data Chemistry


10.0
21.4
12.1
-28.5
-20.7
-54.0
-139.9
-292.5
79.3
39.9
28.3
-0.2
46.7
35.7
10.0

14.6
18.7
20.3
21.6
26.5
26.8
27.6

11.5
13.2
16.2

4.7: Amines
An NH, group attached to an alkyl chain causes a downfield shift of
about 30 ppm at C-l, a down field shift of about I I ppm at C-2, and an upfield
shift of about 4.0 ppm at C-3. The NH) + group shows a somewhat smaller
effect. N-alkylation increases the downfield effect of the NH2 group at C-I.
Shift positions for selected acyclic and alicyclic amines are given in Table
4.14A.

Table 4.14A: Shift positions of Acyclic and Alicyclic Amines (neat, ppm
from TMS)
Compound
CH)NH2
CH)CH2NH2
CH)CH2CH 2NH 2
CH)CHFH 2CH 2NH 2
(CH))N
CH)CH 2N(CH)2
Cyclohexylamine
N-MethyIcycIohexylamine

C-I
26.9
35.9
44.9
42.3
47.5
58.2
504
58.6

C-2

C-3

C-4

17.7
27.3
36.7

11.2
20.4

14.0

13.8
36.7
33.3

25.7
25. I

25.1
26.3
(N-CH 3 33.5)

4.8: Thiols, Sulfides, and Disulfides


Since the electronegativity of sulfur is considerably less than that of
oxygen, sulfur causes a correspondingly smaller chemical shift. Examples of
thiols, sulfides, and disulfides are given in Table 4. I 4 B

iJC NMR

S~ctroscopy

115

Table 4.148: Shift positions ofThiols, Sulfides, and Disulfides (ppm from TMS)
Compounds
C-l
C-2
C-3
CH)SH
6.5
CH)CH 2SH
19.8
17.3
CH)CH 2CH 2SH
26.4
27.6
12.6
CH)CH 2CH 2CH 2SH
23.7
35.7
21.0
(CHJ)2S
19.3
(CH)CH2)2S
25.5
14.8
(CHFH2CH2)2S
34.3
23.2
13.7
(CH)CHFH2CH2)2S
34.1
31.4
22.0
CH)SSCH)
22.0
(CHFH 2SSCHFH)
32.8
14.5

4.9: Functional Groups Containing Carbon


Carbon- 13 C NMR spectrometry permits direct observation of carbon
containing functional groups. With the exception of CH=O, the presence of
these groups could not be directly ascertained by 'H NMR.
4.9.1. Ketones and Aldehyde:
Table 4.15 presents chemical shifts of the C=O group of some ketones
aldehydes. Because of rather large solvent effects, there are differences of
several parts per million from different literature sources.
Table 4.15: Shift positions of the C=O Group and Other carbon Atoms
of Ketones and Aldehydes (ppm from TMS)
Y9

)SA

/C~
79/,

H~C
.

~2111
'i

.,

.,

CH.,
~

" /

H 2 C, ---CH 2
i

CH 3

"'lox"

- -C - -- --- CH 2
/

~7X

116

Spectroscopic Data Chemistry

o
I'

:I I~H

12K2

12~/C,,'
i'

11.l71

1.12Y~

"CH1

1~.N7

ClIO

263-

o
121\ 9

i2~CS
)
136~ CHO
1142'.~"''''

4.9.2. Carboxylic Acids, Ester, Chlorides Anhydrides, Amides and Nitriles:


The C=O groups of carboxylic acids and derivatives are in the range of
150-185 ppm. Nitriles absorb in the range of 115-125 ppm.

"C NMR Spectroscopy

117

Table 4. t 6: Shift Positions for the C=O group and other carbon atoms of
carboxylic acids, esters, Icatones, chlorides, anhydrides,
amides, carhamates, and nitriles (ppm from TMS)
CH3

12K0

~
206

17RI

)-1 1

CH3---COOH
a

CH~
IR R

IR-IR

CH--- - COOH

~C~

H2~

COOH

1.119

173 2

0
[
1337~13!12
~119-l

R9 1

1680

CCI 3 ----- COOH

1150

1630

F"C---- COOH
-

17~()

;---COOH

12R-I

NH2

IRI 5

CH 3 - - COONa"
b

51.5

CH

./"-

CH 3
17.2 -

172

"-

COOH
1761

118

Spectroscopic Data Chemistry

o
1I15X I
1153

M 7

/C"

CH,

"0/

F,C

~"'"

CH,
IH'

0
t

/~IZ

133.1

II

CH 3 --C--C1

1353

J69.5

CI

1313

12R9

?<

~o

I3C NMR Spectroscopy

119

o
"

o
2

Ii

HCNH}
1~5

I3

CH,CN
117 7

10K

IOn

Cl-l-;/
.

CH

2""

110 ~

CN

IIX 7

~CN

'

1327!~132n
129 I

120

Spectroscopic Data Chemistry

a. In CHCI 3 (~50%)
b. Saturated aqueous solution of CH) COON a
c. Neat or saturated solution
d. In H20
e. In DMSO
f. In dioxane (~50%)

4.9.3 Oximes : The simple oximes absorb in the range of 145-165 ppm. For
example

4.10: Spin Coupling


The \3C_I3C coupling is usually not observed, except in compounds
that have been deliberately enriched with I3C, because of the low probability
of two adjacent I)C 1 atoms in a molecule. One bond I3C-H coupling CJCH )
ranges from about 110 to 320 Hz, increasing with increased s character of the
I3C-H bond, with substitution on the carbon atom of electron withdrawing
groups, and with angular distortion. Appreciable I3C-H coupling also extends
over two or more (n) bonds (nJ CH ). Tabl~ 4.17 gives some representative CJ CH)
values. Table 4.18 gives some representative JCH) values, which range from
about -5 to 60 Hz.

Table 4.17: Some (IJ CH) Values


Compound

J(Hz)

SP)
CHJCH)

124.9

CH)~H2CH)

119.2
114.2

(CH))CH
CH JNH 2
CHpH
CH 3 CI
CH 2CI 2
CHCI)

133.0
141.0
150.0
178.0
209.0

121

UC NMR Spectroscopy

C)-H

o-H
QH
[>-H

123.0

128.0

134.0

161.0

205.0

CH2=CH 2

156.2

CH3-~H=C(CH3)2

148.4

Sp2

CH3~H=O

172.4

NH~H=O

188.3

C6 H6
sp

159.0

CH=CH

249.0

C6 HsC=CH

251.0

HC=N

269.0

Table 4.18: Some eJCH) Values


Compound

J(HZ)

Sp3
C.!:i3~H3
C.!:i3~CI3

-4.5
5.9

122

Spectroscopic Data Chemistry


~H/.'H~'O

26.7

Sp2

~H:=CH2

--2.4

(CtI)~=O

5.5

CH2=~HCH=O

26.9

CoHo
sp

1.0

CH=iJI

49.3

C6HsO~=CH

61.0

Table 4.19: Coupling Constants for 31 p,


IJ(HZ)

Compound

19F,

and D coupled to
2J(HZ)

13c.

3J(HZ)

271

Cl\CF3
CF2H 2

235

CF3CO zH

284

43.7

C 6 Hl

245

21.0

(CH 3CH)l

5.4

10.0

(CHFHz)l+Br-

49

4.3

(C 6 H s)l+CH 3I

88(CH3 52)
143

CH3CHl(OCH2CH3)2

II

0
CDCll

31.5

CDFCD 3

19.5

II

(CD)2S0

22.0
D

D
25.5
D

D
D

10.9
7.1U cop 6.9)

Jccop

6-2

1JC NMR Spectroscopy

123

4.11: The 13C Chemical Shifts, Couplings, and Multiplicities of


Common NMR Solvents
o(ppm) JC-D(HZ) Multiplicity

Structure

Name

CDCl J
CDpD
CD 3SOCD3

Chloroform-d,
Methanol-d 4

77.0
49.0

32
21.5

Triplet
Septet

DMSO-D 6

39.7

21

Septet

DMF-d 7

30.1

21

Septet

35.2

21

Septet

167.7

Triplet

II
DCN(CD3)2

C6D6
D2C-CD2

I I0

92

D2~

Benzene-d6

128.0

30
24

THF-ds

25.2

20.5

67.4

22

Quintet
Quintet

Dioxane-ds

66.5

22

Quintet

Pyridine-ds

123.5 (C-3,5)

25

Triplet

p\

D2C CO2

II

Triplet

D8FD2
0
D

D~(

135.5 (C-4)

24.5

Triplet

149.2 (C-2,6)

27.5

Triplet

29.8(methyl)

20
<1

Septet

II

CD 3CCD J

Acetone-d6

206.5 (carbonyl)
CD3CN
CDJNO:!

Acetonitrile-d3
N itromethan -d J

1.3(methyl)

Septetb

118.2(CN)

32
<I

Septetb

60.5

23.5

Septet

Septet

124

Spectroscopic Data Chemistry

CD 3CDPD
(CD 3CD2 )P

Ethanol-d 6
Ether-d 1o

[(CD3)2N]3 p=o HMPA-d ls


Acetic acid-d 4
CD 3COP
CD 2C1 2

15.8(C2)

19.5

Septet

55.4(C-J)

22

Quintet

13.4 (C-2)

19

Septet

64.3(C--I)

21

Quintet

35.8

21

Septet

20.0(C-2)

20

Septet

178.4(C-I)

<1

Septetb

29

Quintet

53.1
Dichloromethane-d2
(Methylene chloride-d2)

Triplet intensities = 1: 1: 1, quintet = 1:2:3:2: 1, septet = 1:3:6:7:6:3: 1.

Unresolved, long. range coupling.

4.12: The 13C Correlation Table for Chemical Classes


R = H or alkyl substituents
Y = Polar substituents
Types and group

o(ppm)

Acyclic hydrocarbons
-CH J

-CHz

iH
I
i-

8-30
14-55
24-59
30-40

Aticyc\ic hydrocarbons

C3H6

15-19

C4 HS to CIOHzo

21-29

Alkenes
HzC =C-R
HzC=C-Y
C=C-C=C-R

102-121 (HF=)
109-150 (=C-R)
80-170
109-151

125

i3C NMR Spectroscopy


Allenes

70-97(=C)
200-214 (=C=)

C=C=C
Alkynes

63-73 (HC=)
71-89 (=C-R)
20-94

C=C-R
C=C-y
Aromatics
Ar-R
Ar-Y
Heteroaromatics
Alcohols C-OH
Ethers C---O--C
Acetals, Ketals O-C-O

120--150
94-158
100-166
44-86
54--86
8-12

Halides

C-F'_3
C-CI'-4
C-Brl-4
C-I,_4
Amines C-NR2
Nitro C-NO z
Mercaptans, Sulfides C-S-R

72-134
20-98
-28.5-+33
-292.5-+42
20-70
60-78
5.5-46

Sulfoxides, Sulfones
C-SO-R, C-S0 2-R
Aldehydes, Sat. R-CHO
Aldehydes, a,

13- unsat. R-C=C-CH=O

Ketones, Sat. R2C=O


Ketones, a,

36-54
197-220
176-194
195-220

13 unsat.

R-C=C-C=O

182-212

Carboxylic acids, sat.


R-COOH
Salts RCOOCarboxylic acids a, l3-unsat.

166-186
174-194

126

Spectroscopic Data Chemistry


R--C=C-COOH
Esters, sat. R-COOR I
Esters, a, ~- unsat.
R-C=C-COORI

159--174
158-177
153-172
148-174
150-177
108-124
144-166

Anhydrides (RCO)P
Amides RCONH 2
Nitriles RC=N
Oximes RF=NOH
Carbamates
RzNCOOR '
Isocyanates
R-N=C=O
Cyanates R-O-C=N
Isothiocyanates
R-N=C=S
Thiocyanates
R-S-C=N
13C

151-160
111-134
104-120
116-141
98-118

NMR data for several natural products (0)

';(9r- '"

30.8

2" 1

.,,~ ..

~ ......
'011
12. ~

39.7

011

22 ~

2" "

2~.1

2~

17.4

17.~

)06

28.0

'2~3

2D
n,Citral
no/eral, Citral Itl
2\.7

2'.1

222

2ft

21.2

\.1031001

Geraniol

1208

,"

III .'
124 "

1130 ,

131.2\

Myrcene

24.4

!7':

1".8

112.9

248

1ZO.7
Z~

'I

0'
P"'"

30 9
2\ (,

44 (,

~OH

20 $

108 .
Lim.nene

206
a.Trrp,nrne

2" 7
27 1
() Tcrplncol

227
"'Jleaunc

IlC NMR Spectroscopy


127
20.0

19

387

~b

26.1

20.4

lU

)01

21.'

27.0
IO~.9

Norbomanc

/J-I'IOC",

a-Pinene

Camphor

n.5
\

42.4

22.'

121.1
ChoI..urol

lUOll
;. . .

1J.4.9 68 \}

ill.6

.40

0
N

1'" \} N

no

..,. I

1.9.~

CHI

40.3

41.4
CH.-N

:5.'

'1.5

'O,e".

I.)

.WI

H."

OC
110.S
1l1.0

~
HO

11;;0)7.1

6U

(,2.5

OH

HO

6504

~, 8

Nic;Olinc

1716

21

Ill.'

. 11.
OH
OH 97.4

77.'

129 I
.

COCAIM

IOO'9~~H

1.).ol,.~2
N
0

Uril

000

5
Mass Spectrometry

A mass spectrum is a presentation of the masses ofthe positively charged


fragments versus their relative concentrations.
The commonest method of presentation is either a-bar graph or a
percentage table.
Mass spectra are routinely obtained at an electron beam energy of70e V.
The simplest event that occurs is the removal of a single electron from the
molecule in the gas phase by an electron of the electron beam to form the
molecular ion, which is a radical cation (M:). The symbol: indicates that
the molecule has lost an electron, it has unpaired electron and is positively
charged.
70eV
M-----4) M:
+ e
Molecule
Molecular
ion
If some of the molecular (parent) ions remain intact long enough to
reach the detector, we see a molecular ion peak. It is important to recognize
the molecular ion peak because this gives the molecular weight of the compound.
The molecular ion peak is usually the peak of highest mass number except for
the isotope peaks.
The molecular ion in tum produces a series of fragment ions.
The most intense peak in the spectrum called the base peak is assigned

129

Mass Spectrometry

a value of I 00%, and the intensities of the other peaks, including the molecular
ion peak, are reported as percentage of the base peak. Of course, the molecular
ion peak may sometimes be the base peak.
The molecular ion in turn produces a series of fragment ions as shown
for benzamide:

C6HsC=0
mle 105

l-eo

\lI

(0)mle77
Table 5.1: Exact Masses of Isotopes
Mass

Element

Atomic Weight

Nuclide

Hydrogen

1.00794

IH

1.00783

12.01115

DeH)
12C

2.01410
13.00336

14.0067

\3C
14N
ISN

15.0001

160

15.9949

17

0
180

16.9991

19F

18.9984

Carbon
Nitrogen
Oxygen

Fluorine

15.9994

18.9984

12.00000 (std)
14.0031

17.9992

Spectroscopic Data Chemistry

130

Silicon

28Si
29Si
30Si
3!p

28.0855

Phosphorus
Sulfur

30.9738

79.9094

Iodine

126.9045

29.9738
30.9738
31.9721
32.9715
33.9679

35Cl
37Cl
79Br
slBr
1271

35.4527

BroTnitfe

28.9765

32S
33S
34S

32.066

Chlorine

27.9769

34.9689
36.9659
78.9183
80.9163
126.9045

Table 5.2: Relative isotope Abundances of Common Elements


Relative
Relative
Relative
Elements Isotope Abundance Isotope Abundance Isotope Abundance

Carbon
Hydrogen
Nitrogen
Oxygen
Fluorine
Silicon
Phosphorus
Sulfur
Chlorine
Bromine
Iodine

12C

100

IH
14N
160

100

19p

100

2sSi

100

31p
32S
35CI
79Br
1271

100

100

i3C
2H
15N

100

!70

0.38
0.04

ISO

0.20

9Si

5.10

30Si

3.35

33S

0.78

34S

4.40

37CI
slBr

32.5

100
100
100

1.11

0.016

98.0

100

Peaks attributable to isotopes can help identity the compound responsible


for a mass spectrum.
For example
CH3CH2CH2CH2CH3

70 eV )[CH 3(CH 2hCH 3]t +eMolecular ion


mlz= 72

131

Mass Spectrometry

Although the molecular ion of pentane have mlz value of 72, its mass
spectrum shows a very small peak at m/z = 73. This is called an M+ I peak
because the ion responsible for this peak is one unit heavier than the molecular
ion. The M+ 1 peak occurs because there are two naturally occuring isotopes
of carbon : 98.89% of natural carbon 12C' and 1.11% is l3C'. The M+I fragment
results from molecular ions that contain one 13C' instead of a 12C'.
Above table shows that the M+ 1 peak can be used to determine the
number of carbon atoms in a compound because the contributions to the M+ 1
peak by isotopes of H,

and the halogens.are very small.

Presence of an isotopic peak at (M+ + 2) indicates the presence of four


elements 0, S, Br, Cl.
The presence ofa large M+2 peak is evidence ofa compound containing
either chlorine or bromine, because each of these elements has a high percentage
of a naturally occuring isotope two unit heavier than the most abundant isotope.
If the M+2 peak is one-third the height ofthe molecular ion peak, the
compound contains a chlorine atom because the natural abundance of 37CI is
one-third that of the 35Cl.
If the M and M+2 peaks are of about the same height, the compound
contains a bromine atom because the natural abundances of 79Br and slBr are
of about the same.

Recognition of the Molecular ion Peak


Many peaks can be ruled out as possible molecular ions simply on
grounds of reasonable structure requirements. The nitrogen rule is often helpful.
It states that a molecule of even-numbered molecular weight must contain
either no nitrogen or an even number of nitrogen atoms; an odd-numbered

molecular weight requires an odd number of nitrogen atoms. (for the nitrogen
rule to hold, only unit atomic masses i.e., integers are used in calculating the
formula masses)
This rule holds for all compounds containing carbon, hydrogen, oxygen,
nitrogen, sulfur, and the halogens, as well as many ofthe less usual atoms such
as phosphorus, boron, silicon, arsenic, and the alkaline earths.

132

Spectroscopic Data Chemistry


The intensity of the molecular ion peak depends on the stability of the

molecular ion. The most stable molecular ions are those of purely aromatic
systems.
In general the following group ofcompounds will, in order of decreasing
ability, give prominent molecular ion peaks: aromatic compounds> conjugated
alkenes > cyclic compounds > organic sulfides > short, normal alkanes >
mercaptans.
Recognisable molecular ions are usually produced for these compounds
in order of decreasing ability:
ketones> amines > esters> ethers> carboxylic acids - aldehydes amides - halides.
The molecular ion is frequently not detectable in aliphatic alcohols,
nitrites, nitrates, nitro compounds, nitriles and in highly branched compounds.
The presence of an M-15 peak (loss of CH3), or an M-18 peak (loss of
HP), or an M-31 peak (loss ofOCH 3 from methyl esters) and so on, is taken
as confirmation of a molecular ion peak. An M-l peak is common and
occasionally and M-2 peak (loss ofH2 by either fragmentation or thermolysis)
or even a rare M-3 peak (from alcohols) is reasonable. Peaks in the range of
M-3 to M-14, however, indicate that contaminants may be present or that the
presumed molecular ion peak is actually a fragment ion peak.
Losses of fragments of masses 19-25 are also unlikely (except for loss
ofF = 19 ofHF = 20 from fluorinated compounds) loss of 16(0), 17(OH), or
18(HP) are likely only if an oxygen atom is in the molecule.

Summary of Fragmentation Processes


(1) Hydro carbons:
(a) Alkanes:

Straight chain alkanes show low intensity molecular ion peaks. The
intensities of these peaks decrease with increasing chain length.

Since straight chain alkanes rarely eliminate methyl groups (--CH 3)

133

Mass Spectrometry

peaks corresponding to (M-15) are absent, or are of low intensity,


in the spectra of long chain paraffins.

Elimination of -C 2H s' -C 3 H7' from the molecular ion gives peaks


at masses C n H2n+1 (m/e = 29, 43, 57, 71 and 85). These peaks are
most intense in the C 2 to C s range. The peaks at 43 or 57 are usually
the base peaks, due to the remarkable stabilities of the propyl ion
(-C 3H/) and the butyl ion (-C4H9+)'
The intensities of other peaks 14 mass units (-CH 2) apart (71,85,
etc.) decrease with the increasing weight of the fragment. These
peaks 14 units apart appear as clusters because each prominent
peak is accompanied by a smaller peak one unit higher due to 13C
and a few small peaks one and two units lower, due to the loss of
hydrogen atoms.

In branched alkanes, there is a tendency for the bonds to rupture at


the branches resulting in the formation of relatively stable secondary
and tertiary carbonium ions.

Molecular ion peaks are more abundant in cycloparaffins than in


straight chain paraffins containing the same number of carbon atoms,
although the cyclic compounds tend to lose their side chains.

If the ring undergoes fragmentation, it loses two carbon atoms


simultaneously, thus producing an abundance of+C 2H4 (m/e 28), +C2HS (m/e
29), and M-28, M-29 ions in the spectrum. Due to this tendency to lose ethylene
C2H4 and other even-mass number fragments, the percentage of fragments
having even mass number are usually higher in the spectra of cycloparaffins
than in those of acyclic hydrocarbons.
Mechanisms for fragmentations of different types of alkanes are believed
to be as follows:

(i) Straight chain alkanes


CH3CH2CH2CH2CH2CH3
alkane

""

. ..
100l~:tlon) CH 3CH; +CH 2CH 2CH 2CH 3
(Parent ion)

134

Spectroscopic Data Chemistry

<

CH 3CH; + CH] -CH2 -CH] -CH3


(radical)
(ion)

mfe 29

+~

C H2

hemi - heterolysis
followed by

mfe 57

CH 2

heterolysis
-CH

mle 57

(ion)

2 ) CH 2 + C H 2 - CH 2 - CH 2
(m/e 14)
mle 43

CH 2 - CH 3

(ii) Branched chain alkanes


CH 3

CH 3

CH 3 -CH2 -C-CH3

CH 3
alkane

JC\

IOnIsation) CH - CR- + C - CH
at the most
3
2 I
3
polar bond
CH
3
Parent ion

<

hemi - heterolysis

(iii) Cycloalkanes

y
ionisation

alkane

O~
Parent ion
hemi-heterolysis

accompanied by

c.

radical ion

heterolysis of ~ . y bond

135

Mass Spectrometry
(b) Alkenes

Alkenes readily produce molecular ions by losing a 1t-electron.


As in alkanes, so in alkenes, the intensity of the M peak decreases
with increasing molecular weight.

The most intense peak (usually the base peak) in the spectra of
ole fins is due to the stable, charged species produced by allylic
cleavage, that is, by the rupture of the C-C bond

to the double

bond. The fragment carrying the double bond is usually the charged
species.

H 2 C- CH = CH 2 + R
rnIe 41
The natural outcome of allylic cleavage is a series of fragments at
masses 41,55,69, 83, etc., with the general formula CnH 2n _ t (allyl
carbonium ions)

McLafferty rearrangements are also common in these ions. These


rearrangments produce ions of the general formula CnH2n

Cyclic alkenes usually show a distinct molecular ion peak. A unique


mode of cleavage is the retro-Diels-Alder reaction shown by
limonene:

+
(i)

>

[~r
II "

136

Spectroscopic Data Chemistry

CH?

(ii)

II CH 2

(c) Aromatic hydro carbons

An

a~omatic

ring in a molecule stabilises the molecular ion peak,

which is usually sufficiently large that accurate intensity


measurements can be made on the M+I and M+2 peaks.

In alkyl benzenes the most probable cleavage is at the bond

to

the ring. This gives rise to a base peak at mle 91 due to the formation
oftropyllium ion.

mle = 91
However, in compounds containing substituents on the a-carbon atom,
the base peak may have masses higher than 91 by increments of 14, representing
substituted tropyllium ions

mle 105

mle = 105
A strong peak at mle

92 is observed in the case of many compounds

containing a propyl or longer side chain. This peak is due to the +C 7Hg ion
produced by the McLafferty rearrangement.

137

Mass Spectrometry
CH,

II -

CH

R/
mle = 92
Fragmentation ofa tropyllium ion into a cyclopentyl cation, +CsHs' and
a cyclopropenium ion +C3H3' results in significant peaks at mle = 65

mle = 39

mle = 91

mle = 65
Cyclopentylcation

Cyclopropenium ion

A characteristic cluster of ions resulting from an a cleavage and hydrogen


migration in monoallcylbenzenes appears at mle 77 (C 6 H/), 78 (C 6 H/) and
79 (C 6 H7+).

(2) Hydroxy compounds


(a) Alcohols:

In the spectra of alcohols, the molecular ion peak M is usually


either very small or totally absent. It is somewhat more abundant in
the spectra of secondary than in those of primary and tertiary
alcohols.

The odd-electron molecular ion is produced initially by the removal of


an n-electron from oxygen:

R-O-H_-_e_~) R-O-H
The odd-electron molecular ion readily decomposes into stable products.
One such decomposition involves energetically favoured a-cleavage.
This cleavage leads to more stable, even-electron, oxonium ions.

138

Spectroscopic Data Chemistry

Methanol
+

H +H 2 C = O-H

mle = 31
M-l

Ethanol

Although ethanol shows an M-l peak at mle = 45 by a-elimination of a


hydrogen radical, the M-15 peak is more intense because a-elimination of a
larger substituent is always favoured.

In the spectra of primary alcohols, in addition to the M-l peak,


very low intensity M-2 and M-3 peaks are also observed.
H

.;

R-C-O-H

)R-C

=O-H

(M-l)

.
+

) R-C =0

H
(M-2)

l-H"
R-C=O

(M-3)

All primary alcohols (except methanol) and high molecular-weight


secondary and tertiary alcohols display peaks at M-18 due to the
loss of H20 through a cyclic mechanism.

139

Mass Spectrometry

(m-IS)

+Hp

In cyclic alcohols, the principal dehydration process involves loss


of a hydroxyl group together with a hydrogen atom from either C 3
or C4 to produce bicyclo ions.

OH

~H
l

H fromC 3

[0 r

-HP, H fiom C4
when cyclohexanol is
in the boat form

Butanol & longer-chain primary alcohols often suffer double


elimination. That is, they lose one molecule of water and one of
ethylene simultaneously through a six-numbered cyclic mechanism,
thus displaying an M-46 peak

140

Spectroscopic Data Chemistry

"'..;

~'-.CHR
HC
2

H,C,

/C"""

/
C-C

/ \

/\

HHHH

+/HR

-~

m=28

/C"""
H

+ Hp

M-46

The most probable site of cleavage, resulting in a very intense peak,


is the bond 13 to the oxygen atom in alcohols. This cleavage gives a
strong peak at mle = 31 (CHPHt in the spectra of primary alcohols,
while secondary and tertiary alcohols display analogous peaks at

mle = 45 (MeCHOHt and mle = 59 [(CH3)2COHt.

Unsaturated alcohols generally behave like their saturated analogs.


However, the stability of the allyl system decreases the probability
of cleavage adjacent to the double bond.

1:

-He

R-CH = CH4~ 0 H - - - + ) R-CH = CH = 0 H


H

(M-l)
very intense

(abundant)

R-CH=~~H---+R-CH=CH+CH2=OH
I
H

(less abundant)

(b) Phenols and other aromatic alcohols:

As in all aromatic compounds, the molecular-ion peak M in phenol


and aromatic alcohols is strong. In phenols it forms the base peak.

The M-I peak due to the loss of hydrogen is small in phenol, but is
very strong in cresols and benzyl alcohols. The production ofM-l
ions is due to the random abstraction of hydrogen bonded to any of
the carbon atoms to produce a resonance-stabilised.
system such as hydroxy tropyllium ions.

7t

complex

141

Mass Spectrometry

OH

<E-<--

M-I

[p-Cresol] +

[Benzyl alcohol] +

Hydroxytropyllium
ions

The most important fragmentation in phenols and benzyl alcohols


is due to the loss of CO and CHO giving peaks corresponding to
M-28 and M-29, respectively.

OH

~(---~
)

[6~J
mle =94 (M)
100%

[Phenol]"t

l-CO

[6J

_Ho

mle = 66
(M-28)

[Cyclopentyl cation]
mle = 65
(M-29)

_HO

(M-I)

mle = 108

Random
_H o

0' ,

I, + )
.,._....

mle = 107
(M-I)

C=O

CH~C=I H
H

I
I

...
6<
H

(+

\ .....,

OH

Spectroscopic Data Chemistry

142

,0
mle = 79

(M-29)

mle

77

(M-31)

Methyl-substituted phenols (Cresols), other hydroxybenzenes


(catechol, resorcinol, hydroquinone) and methyl-substituted benzyl
alcohols display M-18 peaks due to loss of water.
The dehydration is more pronounced if the substituents are ortho
to each other.

a::J

~L
(M)

(M-18, 100%)

Ethers:
A molecular ion of ether is formed by the removal of one of the
nonbonded electrons on oxygen, and, just as with alcohols, the molecular ions
of ethers are unstable and readily undergo a-cleavage. (cleavage of a bond 13
to oxygen).

-r'\ b(~

CH 3CH 2;

loss of
+
C H -O-CH2CH3 ----,.:---~) C H = O-CH 2CH 3
1
1
C2 Hs
CH 3
CH 3
(m/e = 73)

This type of cleavage usually accounts for the base peak and some strong
peaks at 45, 59, 73 etc.

In ethers, unlike the case of alcohols, cleavage of bonds a to oxygen


can also occur.

Mass Spectrometry

143

R-O-R'

heterolysis) R-O +

R'

In such a cleavage, the alkyl portion carries the charge and accounts for
hydrocarbon peaks at m/e = 29, 43, 57, 71 etc.

Homolytic fission of bonds a to oxygen may often be accompanied


by rearrangement of one hydrogen atom to eliminate an olefin.

H-f~H2
I

CH 3CH 2-C

~;

CH3

'\

H.
I
CH 2

/CH2~CH3CH2-C-OH+

,-

'/}

CH3

II

CH 2

Aromatic ethers display a somewhat stronger M peak, and show a


fragmentation behaviour similar to that of aliphatic ethers.

(i) Cleavage of bonds a to oxygen can be homolytic or heterolytic.

(\ ;)-J-CH2CH3 _-O
_ _C_H-=.2_CH---=-34)

(ii) Cleavage of bond a to oxygen with rearrangement of hydrogen to

eliminate an alkene.

Aldehydes and Ketones:


Organic carbonyl compounds, like other oxygen containing compounds,
undergo the loss of one of the lone-pair electrons of the oxygen atom.

144

Spectroscopic Data Chemistry

The molecular ion thus produced can undergo fragmentation either


through the more favourable a-cleavage or, if a concerted migration of y
hydrogen to oxygen is possible, through ~-cleavage.

R,..., _

,'(c4-0+ __a_c_le_a_v_ag=-e-t) R I -C == +0+ R

R/
I

homolytic

oxonium
ion

When a y hydrogen is available for migration, ~-cleavage results in the


formation of an olefin and a charged enol through the McLafferty
rearrangement.
R2....... .....<1-1' ~
. . . . CH ~ '0
~ _ cleavage R2CH
I~
,-..j I
----!----=-~)"
/CH
~C-R involving a
RICH
RI
CH 2
concerted
electrocyclic
rearrangement

(a) Aldehydes:

Aliphatic as well as aromatic aldehydes display molecular-ion peaks.


The M peak is prominent in aromatic aldehydes, whereas the
intensity ofthe M peak in aliphatic aldehydes decreases rapidly in
compounds containing more than four carbon atoms.

In aldehydes, the M-I peak is usually as intense as the M peak. The


peak results from the loss of hydrogen through homolytic acleavage.
.f'+
+
R-C = O~ R-C == O+H
(M -I)
H

tJ'

In lower aldehydes (C,-C 3), a-clea-vage results in the formation of


+
the stable formyl ion (H - C == 0), which forms the base peak.
o

R-C =

O~

H-C==O+R
mfe =29
basepeak

145

Mass Spectrometry

However, with straight chain aldehydes of higher molecular weight,


this peak is approximately 40% of the base peak which may be displayed at
M-29 due to ions produced through heterolytic cleavage as;

R-C

=O~

R+ + C=O
(M-29)
I
H

The base peak in butyraldehyde and in many higher aliphatic


aldehydes results from

~-cleavage.

In butyraldehyde this peak is at mle = 44, which must be a peak for a


rearranged ion because it has an even mass number. In compounds containing
C, H and 0', peaks resulting from simple cleavage always appear at odd mass
number, but the peaks due to rearranged ion have an even mle ratio.

H",+

o
I

C-H

II

CH 2

[n-butyraldehyde] +

mle =44

(b) Ketones:

The parent-ion peak M in ketones is of significant intensity being


greater for the low-molecular weight (upto eight carbons) than for
the high-molecular weight ketones.

a-cleavage in ketones can produce more stable R-C=O' ions.

mle = 43, 57, 71 etc.

146

Spectroscopic Data Chemistry

<O)-~)'1=H3 _~~~olysis ) <O)~)

m/e = 105

Acetophenone +

heterolysis

,I

+CO

mle = 77

McLafferty rearrangements (l3-cleavage with migration of yhydrogen) are common in ketones containing a chain of three or
more carbon atoms attached to the carbonyl group. However,
complications arise due to the following facts:

(a) The mass of the ion produced by the migration ofa single hydrogen
varies with the number of carbon atoms in the alkyl group (R) which
is not involved in the rearrangement.

H,,,;

o
I

+ C-R

II

CH 2

mle = 58, 72, 86 etc.


(b) Ifboth the alkyl groups in the ketone contain three or more carbons,
double rearrangement produces the enolic catiofl, which can again
undergo l3-cleavage involving the y-hydrogen on the second alkyl
group.

H~

.
c .~
. .1'
Ir--"

HC

Ht

(CH 2

CH

C;/ 2 CH 2
~I
----~ I
+
II
H2 C~CH2 rearrangement CH 3 CH 2
H
mle = 58
'"

"-

sec ond

"'-,--:::

147

Mass Spectrometry

If the y-carbon in either of the alkyl groups is substituted, the order


of migration of the y-hydrogen is found to be tertiary> secondary
> primary, and the rearrangement preferentially involves the larger
alkyl groups.

Carboxylic acids and esters

Aliphatic monocarboxylic acids and their esters generally display


a weak but noticeable molecular-ion peak.
Aromatic monocarboxylic acids and esters, like other aromatic
compounds, display a strong M peak.

Like other oxy compounds, cleavage of the bond [3 to carbonyl ([3cleavage), together with the rearrangement of y-hydrogen
(McLafferty rearrangement) is the most important mode of
fragmentation of carboxylic acids.
In monocarboxylic acids, this fragmentation produces ions (I) which
exhibit a characteristic peak at mle = 60

A corresponding [3-cJeavage peak in methyl esters appears at


mle

= 74 due to (II).

H 2C

+
/OH
C ..............
OCH 3

II

Analogous peaks in ethyl and butyl esters appear at 88 and 116,


respectively.

148

Spectroscopic Data Chemistry

In acids and esters, a similar cleavage of a bond a to carbon)'1 can


produce four kinds of ions.

+
+
~O
-?-O
.
+
R g C'-......
can gIve R or C
............. OR!
OR!
T
,J,
1
mle = 15,29,43, 57
mle = 45, 59, 73, 87 etc.
(M-45, M-59 etc.)
(M-I5, M-29, M-43 etc.)
~

-::;::::-0

R-C.............

can give

OR!

~O

mle= 17,31,45,5getc.
(M-43, M-47 etc.)

R_C'l"

or

OR!

mle = 43,57, 71 etc.


(M-17, M-31, M-45 etc.)

In aromatic acids containing a methyl group ortho to the carboxyl,


elimination ofa stable molecule ofwater produces a peak at M-18.
This elimination is so important that in o-toluic acid the M-18 peak
is the base peak.

ace

"~

~H ~~:~e

CH 2
(M = 136)

C=O

C(H
mle

= 118 (M-18)

149

Mass Spectrometry

Dibasic acids show a peak at M-90 due to the loss of both carboxyls
through a-cleavage.

Amines
In amines, as in oxygen containing compounds such as alcohols, ketones,
aldehydes, etc., the initial ionisation process occurs through the loss of a
non bonded electron on the hetero atom, nitrogen.

The molecular-ion peak M is weak to absent in high-molecular


weight aliphatic open-chain amines, but strong in aromatic and
cyclic amines.

In the case ofmonoamines, if the molecular-ion peak is present, it


appears at an odd mass number in the spectrum. In the case of
other nitrogen compounds also, it appears at odd mass number when
the compound contains an odd number of nitrogen atoms (the
nitrogen rule).

A moderate M-l peak is observed in many aromatic and lowmolecular-weight aliphatic amines due to the loss of a hydrogen
radical.
H

~/H

-H

H-tTN"H

+
) H2C = N H2

M-1

In amines, as in alcohols, the most important fragmentation is that


of the bond

p to

nitrogen. In many amines' this fragmentation is

responsible for the base peak.

I r;/

."

R+-~-N"", ~ R

+/
+/C = N"",

mle = 30, 44, 58,


72,86 etc.

150

Spectroscopic Data Chemistry

In cyclic and aromatic amines, both bonds ~ to nitrogen can rupture.


CH 3
0

/N~
1

"

~.~.r-...~
CH 2

-CH 3

CH 2

I!~
H 2C

6 {oJ

CH 2

mle =42

-HeN

mle = 66

-H

<@
mle = 65

The loss ofHCN and H2CN from aniline is similar to the elimination
of CO and CHO from phenol.

Like other side-chain aromatic compounds, alkyl anilines undergo


~-elimination

of the side chain and show a strong peak at mle =

106 to the aminotropyllium ion

>
mle = 106 (M-I)

If the a-carbon carries substituents, a complicated fragmentation,


involving bonds a and ~ to nitrogen and a migration of~-hydrogen,
can take place in secondary and tertiary amines. For example,

lSI

Mass Spectrometry

CH,

""

C=C

""R

" NI =CH-CH,,
+
+

Amides
The mass spectroscopic behaviour of amides is generally similar to that
of corresponding carboxylic acids.

Amides usually display an easily distinguishable molecular-ion peak


which, if only one amido group is present, manifests itself at odd
mass number in the spectrum.

In amides, as in carboxylic acids, cleavage of a carbon-carbon bond

13 to the carbonyl CI3-c1eavage) is the most important fragmentation


process. In amides which have y-hydrogen available for migration,
the McLafferty rearrangement is equally common. In most primary
amides, the resulting ion usually forms the base peak.

mle = 59

In the case oflong-chain primary amides cleavage of the bond y to


carbonyl can also take place, giving minor peaksat mass 72 (without
rearrangement) and 73 (with rearrangement).

152

Spectroscopic Data Chemistry

Strong peaks are also displayed at m/z

44 by primary amides

(containing upto four carbon atoms), due to rupture of the bond

to nitrogen (or a to carbonyl). This fragmentation is similar to that


observed in amines.

Co
~

'"

~+.

Rt~

~C~+

NH2

NH2

Table 5.3: Masses and Isotopic Abundance Ratios for Various


Combinations of Carbon, Hydrogen, Nitrogen and Oxygen8
FM
16
15.9949

C2H

12.0000

H2N
CH 4

16.0187

26

13.0078

17

13
CH

25

12
C

FM

FM

14
N

14.0031

CH2

14.0157

15

16.0313

25.0078

CN

26.0031

C 2H2

26.0157

HO

17.0027

27

H3 N
18

17.0266

CHN

27.0109

C 2H 3

27.0235

Hp

18.0106

28

24.0000

N2
CO

HN

15.0109

24

CH 3

15.0235

C2

28.0062
27.9949

153

Mass Spectrometry
FM

FM

CH 2N
C2H4

28.0187

38

28.0313

C2N
C3H2

HN2
CHO
CH3N
C2HS

29.0266

39

29.0027
29.0140

C2HN
C3H3

29.0391

40

30

CN 2
29.9980 Cp
30.0218 C2H2N
30.0106 C3H4

29

NO
H2N2
CHP
CH4N
C2H6
31

HNO
H3 N2
CH,0
CHsN
32

2
H2 NO
H4N2
CHP

30.0344
30.0470

CHN2
C2HO
31.0058 C2H3N
31.0297 C3HS
31.0184

42

31.0422

N.>

CNO
31.9898 CH2N2
32.0136 C2 HP
32.0375 C2H4N
32.0262 C3H6

33

H02
H3 NO
34

HP2
36

C3

H2N3
38.0031 CO2
38.0157 CH 2NO
CH4N2
39.0109 C2H4O
39.0235 C2H6N
C3HS
40.0062

HNp
40.0187 H3N3
40.0313 CH02
CH 3NO
41.0140 CHsN2
41.0027 C2HP
41.0266 C2H7N
41.0391

32.9976

HN3
33.0215 CHNO
CH3N2
34.0054 C2H,0
C2HSN
36.0000 C3H7
Np

43.9898
44.0136
44.0375
44.0262
44.0501
44.0626
45.0089
45.0328
44.9976
45.0215
45.0453
45.0340
45.0579

46

N0 2
H2N2O
41.9980 H4N3
42.0218 CHP2
42.0106 CH 4NO
42.0344 CH6N2
42.0470 C2HP
42.0093

45.9929
46.0167
46.0406
46.0054
46.0293
46.0532
46.0419

47

43.0422

HN02
H3 NP
HsN3
CH,02
CHsNO

43.0548

48

44.0011

3
H2N0 2

43.0171
43.0058
43.0297
43.0184

44
37.0078

44.0249

45

39.9949

43

37

C3H

41

FM

47.0007
47.0246
47.0484
47.0133
47.0371
47.9847
48.0085

154

Spectroscopic Data Chemistry


FM

H4Np
CHP2
C4

49
HO,,
H3N0 2
C4H
50
H2 0 3
CN
,
C4H2
51
CHN
,
C4H3
52
C ZN 2

CO
,
C3H2N
C4H4

53
C2HN z
C3HO
C3H3N
C4 H 5
54
CN,,
C2NO
C2H2N2

FM

48.0324
48.0211

C2 HNO
CZH3N2

55.0058

48.0000

C3 HP
C)15N

55.0184

48.9925
49.0164
49.0078
50.0003
50.0031
50.0157
51.0109
51.0235
52.0062
51.9949
52.0187
52.0313
53.0140
53.0027
53.0266
53.0391

C3HP
C3H4N
C4H6

54.0093
53.9980
54.0218
54.0106
54.0344
54.0470

55
CHN,,

55.0171

FM
C]H4NO
C2H6N]

58.0293
58.0419

55.0422

C3H6O
C3HgN

C4H7
56

55.0548

C4H to

58.0783

N4

56.0124

CNP

56.0011

55.0297

59
HN 30
H3N4
CHN02

58.0532
58.0657

59.0120
59.0359
59.0007

CH 2N3

56.0249

CZ0 2

55.9898

CH3NP

59.0246

CzHzNO
CZH4N2
C3H4O

56.0136

CH5N3

59.0484

56.0375

CZH 30 Z

59.0133

56.0262

C2HSNO
C2H7N2

59.0371

C3H6N
C4Hg

56.0501
56.0626

57

C3HP
C3H9N

59.0610
59.0497
59.0736

57.0579

60
N20 2
H2Np
H4N4
C03
CH zN0 2
CH4NP
CH6N3

57.0705

C2H 4OZ

60.0211
60.0449

KO
.'

58.0042

C2H6NO
C2HgN2

H2N4
CN0 2

58.0280

C3HgO
C
5

60.0575

CHzNp

58.0167
58.0406

57.0202

HN4
CHNP

57.0089

~H3N3

57.0328

C2 HO z
CZH3NO
CZH5N2

56.9976

C3HP
C3H7N
C4H9

57.0215
57.0453
57.0340

58

CH 4N 3
C2H20 2

57.9929

58.0054

61
HN 20 2
H3 NP

59.9960
60.0198
60.0437
59.9847
60.0085
60.0324
60.0563

60.0688
60.0000
61.0038
61.0277

155

Mass Spectrometry

H5 N4
CH0 3
CH3N0 2

61.0515

FM

FM

FM

68.0375

64.0187

C3H4N2
C4HP
C4H6N

64.0313

C5Hg

68.0626

64.9874

69
CHN 4

69.0202

C2HNP

69.0089

C2H3N3
C3H02

69.0328

C3H3NO
C3H5N2
C4H5O
C4H7N
C5H9
70

69.0215

64.0062

61.0164

C3N2
C40
C4H2N

CH5NP
CH 7N3

61.0402

C5H4

61.0641

C2HP2
C2H7NO
C5H
62
N0 3

61.0289

65
H0 4
H3N03

61.9878

C3HN2
C4HO
C4H3N

H2NP2

62.0016

C5H5

H4Np
H6N4

62.0355

CHP3

62.0003

65.9953
66.0093

CH4N0 2

62.0242

66
H20 4
C2N3
C3NO

CH6NP
C2H60 2
C4N

62.0480

C3H2N2

66.0218

62.0368

C4HP

62.0031
62.0157

C4H4N
C5H6
67

66.0106
66.0344
66.0470

62.9956

C2HN3
C3HNO
C3H3N2

67.0171

C3HP2

70.0054

67.0058
67.0297

C3H4NO
C3H6N2

70.0293
70.0532

C4 HP
C4 H5N

67.0184

C4 HP
C4HgN

70.0419

C5H7
68
CN 4

67.0548

C5H 1O
71

70.0783

68.0124

CHNP
CH3N4
C2HN0 2
C2H3NP
C2H5N3

71.0120
71.0359
71.0007

C5H2
63
HN03
H3NP2
H5NP
CHP3
CH5N0 2
C4 HN
C5H3
64
4

H2N0 3
H4NP2
CH 4 0 3

60.9925

61.0528
61.0078

62.0594

63.0195
63.0433
63.0082
63.0320
63.0109
63.0235

63.9949

65.0113
65.0140
65.0027
65.0266
65.0391

65.9980

67.0422

63.9796
64.0034

C2NP

C2H2N3

68.0011
68.0249

64.0273

Cpz

67.9598

64.0160

C3H2NO

68.0136

CN.O
,
CH 2N4
C2N02
C2H2NP
C2H4 N3

68.0262
68.0501

68.9976
69.0453
69.0340
69.0579
69.0705
70.0042
70.0280
69.9929
70.0167
70.0406

70.0657

71.0246
71.0484

Spectroscopic Data Chemistry

156
FM

C3HP2
CllsNO
C3H7N2
C4HP
C4H9N

71.0133
71.0371
71.0610
71.0497
71.0736

CsHII
72

71.0861

Np

72.0073
71.9960
72.0198

CNP2
CH2N3O
CH4N4
C20 3
C2H2N0 2
C2H4NP
C2H6N 3

72.0437
71.9847
72.0085
72.0324
72.0563

C3HP2
C3H6NO
C3HgN2
C4HgO
C4H ION

72.0211
72.0449

CSHI2
C6
73
HN 40

72.0939

CHNP2
CH3NP
CHsN4
C2H0 3
C2H3N02
C2HsNp
C2H7N3
C3Hs02

72.0688
72.0575
72.0814

FM

C3H7NO
C3H9N2

73.0528

C4H9O
C4H II N
C6H
74

73.0653

73.0767
73.0892
73.0078
73.9991

FM

C2H9N3
C3HP2
C3H9 NO
CsHN
C6H3
76

75.0798
75.0446
75.0684
75.0109
75.0235
75.9909

74.0355

NP3
H2NP2
H4Np
C04
CH2N0 3

CH6N4

74.0594

CH4NP2

76.0034
76.0273

C2HP3
C2H4N02
C2H6N P
C2HgN 3
C3H60 2

74.0003
74.0242
74.0480
74.0719

CH6NP
CHgN4
C2H40 3
C2H6N0 2
C2HgNp

76.0511
76.0750
76.0160
76.0399
76.0637

C3Hg02
C4N 2

76.0524

Cp

75.9949
76.0187

NP2
H2Np
CN03
CH 2NP2
CH4NP

C3HgNO
C3H ION2
C4H IOO

74.0229
73.9878
74.0116

74.0368
74.0606
74.0845
74.0732

76.0147
76.0386
75.9796

76.0062

74.0031

Cs~N

72.0000

CsN
C6H2
75

74.0157

C6H4
77

76.0313

73.0151
73.0038
73.0277

HNP2
H3 N4O
CHN03

75.0069

76.9987

73.0515

CH 3NP2
CHsNp
CH7N4

HNP3
H3N30 2
HsN40
CH0 4
CH 3N0 3
CH sNP2
CH 7N,G

77.0351

72.9925
73.0164
73.0402
73.0641
73.0289

C2HP3
CzHsN0 2
C2H7NP

75.0308
74.9956
75.0195
75.0433
75.0672
75.0082
75.0320
75.0559

C2Hpj
C2H7N0 2

77.0226
77.0464
76.9874
77.0113
77.0590
77.0238
77.0477

157

Mass Spectrometry

C4HN 2
CsHO
CSH3N
C6HS

CHP4
CH4N0 3
C2H60 3
CH6NP2
C3N3
C4NO
C4H2N2
CsHp
CSH4N
C6H6

79
HN04
H3N20 3

H4NP3
CH 40 4

80.0222
80.0109

CSHgN
C6 H IO

77.0266
77.0391

C2N4

80.0124

83

C3NP
C3H2N 3

80.0011

C2HNP
C2H3N4

83.0120

C3HN0 2
C3H3NP

83.0007

C3 HSN3
C4HP2
C4HsNO

83.0484

83.0610

81.0062

C4H7N2
CsHp
CSH9N

81.0202

C6 HII

83.0861

C2HNP
C3H3N 3
C4 H02
C4H3NO
C4HSN2

81.0089

84
CN 40

84.0073

CsHsO
CSH7N

81.0340

C6Hg

81.0705

77.9827
78.0065
78.0304
78.0542
77.9953
78.0191
78.0317
78.0429
78.0093
77.9980
78.0218
78.0106
78.0344
78.0740

CsHp
CsHsN
C6H7

78.9905
79.0144
79.0382
79.0031
79.0269
79.0171
79.0058
79.0297
79.0184
79.0422
79.0548

80
. H2N04

79.9983

HsNP2
CHP4
CHsN03
C3HN 3
C4HNO
C4 H3N2

82.0657

77.0140
77.0027

78
N04
H2N20 3
H4N30 2
H6NP

FM

FM

FM

CP2
C4H2NO

80.0249
79.9898
80.0136

C4H4N2
CsHp
CSH6N

80.0375

C6Hg

80.0626

81
H3N04
C2HN 4

80.0262
80.0501

81.0328
80.9976
81.0215
81.0453
81.0579

82
C2NP
C2H2N4
C3N0 2

82.0042

C3H2NP
C3H4N3

82.0167

C4HP2
C4 H4NO
C4H6N2
CSH60

82.0054

82.0280
81.9929
82.0406
82.0293
82.0532
82.0419

82.0783

83.0359
83.0246
83.0133
83.0371
83.0497
83.0736

C2NP2
C2H2NP
C2H4N4

83.9960

CP3
C3H2N0 2

83.9847

C3 H4NP
C3 H6N 3
C4H40 2
C4H6NO
C4HgN2

84.0198
84.0437
84.0085
84.0324
84.0563
84.0211
84.0449
84.0688

CSHgO
CsHION

84.0575

C6HI2
C7

84.0939

85
CHN 40

84.0814
84.0000
85.0151

158

Spectroscopic Data Chemistry

FM

FM

FM
C 3H ION 3
C4 Hg02

88.0876

87.0069

C 4 H IONO

88.0763

87.0308

C4H l2N 2

88.1001

86.9956

CSH1P

88.0888

87.0195

C 5N2

88.0662

87.0433

C 60

87.9949

C 2H 7N 4

87.0672

C 6 H2N

88.0187

C 3HP3
C3H5N02

87.0082

C 7H4

88.0313

87.0320

89

C 5HllN

C 3H7NP
C 3H 9N 3

87.0559
87.0798

HNP2

85.0892

CHNP3

89.0100
88.9987

C6 H l3

85.1018

C4 H 70 2

87.0446

CH3NP2

89.0226

C 7H

85.0078

C 4H9NO

87.0684

CH5NP

89.0464

C 4H ll N 2

87.0923

C 2H0 4

88.9874

C 2HNP2
C 2H 3N P

85.0038

C 7H2

85.0277

87

C 2H 5N 4
C 3H0 3

85.0515
84.9925

CHNP2
CH 3N 4O

C 3H 3N0 2

85.0164

C 2HN0 3

C 3H 5N P
C 3H7N 3

85.0402
85.0641

C 2H 3NP2
C 2H 5N P

C 4H 50 2

85.0289

C 4H 7NO

85.0528

C4H9N 2
C 5H 9O

85.0767
85.0653

86

86.0157

88.0524

CNP2
CH 2N 4O

85.9991

C 5H 11 O

87.0810

C 2H 3N0 3

89.0113

86.0229

87.1049

85.9878

C2H 5NP2
C 2H 7N 3O

89.0351

C 2N0 3

C 5Hl3 N
C 6HN

C 2H 2NP2

86.0116

C 7H 3

87.0235

89.0829

C 2 H 4NP

86.0355

88

C 2H9N 4
C 3H 50 3

C 2H 6N 4
C 3H 20 3

86.0594

N 40 2

88.0022

C 3H 7N0 2

89.0477

86.0242

C3H 9N P
C 3HllN3

89.0715

C 3H 4N0 2

CNP3
CH 2N 30 2

87.9909

C 3H6 N P
C 3HgN3

86.0480

CH4N 4 O

88.0386

86.0719

CP4

87.9796

C4 H90 2
C 4H ll NO

89.0841

C 4H 60 2

86.0368

C 2H 2N0 3

88.0034

C SHN2

89.0140

C 4H sNO

86.0606

88.0273

C 6HO

89.0027

C 4 H 1ON z

86.0845

C 2H4NP2
C 2H 6N P

88.0511

86.0732

C 2H gN 4

88.0750

C 6 H 3N
C 7H 5

89.0266

C 5H IOO
C 5Hl2N

86.0970

88.0160

90

C 6Hl4
C 6N

86.1096

C 3HP3
C 3H 6N0 2

88.0399

N 30 3

89.9940

86.0031

C 3HSNP

88.0637

H 2N 40 2

90.0178

86.0003

87.0109

88.0147

89.0590
89.0238

89.0954
89.0603

89.0391

159

Mass Spectrometry

CN04

89.9827

C4HN 3

91.0171

C~NP3

90.0065

CH4NP2
CH6NP

90.0304

CsHNO
CSH3N2

91.0058
91.0297
91.0184

C2HP4
C2H4N0 3

89.9953

C6HP
C6HSN
C7H7
92
NP4
H2N30 3
H4N40 2
CH2N04

91.9858
92.0096

90.0542
90.0191

C2H6NP2
C2HgNp
C2H 1ON4

90.0429

C3H60 3
C3HgN02
C3H ION P
C4H I00 2
C4N 3
C5NO

90.0317

C5~N2

C6HP
C6H4N
C7H6
91
HN30 3
H3NP2
CHN0 4
CH 3NP3
CH5NP2
CH7N4O

90.0668
90.0907
90.0555
90.0794
90.0681
90.0093
89.9980
90.0218
90.0106
90.0344
90.0470
91.0018
91.0257
90.9905
91.0144
91.0382
91.0621

C2HP4
C2H5N0 3

91.0031

C2H7NP2
C2H9NP

01.0508
91.0746

C3HP3
C3H9N0 2

91.0395
91.0634

91.0269

FM

FM

FM

CH4NP3
CH6N 30 2
CHgN40
C2HP4
C2H6N03
C2HgN20 2
C3Hg03
C3N4
C4NP
C4H2N3
C50 2
C5H2NO
C5H4N2
C6HP
C6H6N
C7 HS
93
HNP4
H3 N P3
H5N40 2
CH 3N04

91.0422
91.0548

92.0335
91.9983
92.0222
92.0460
92.0699
92.0109
92.0348
92.0586
92.0473
92.0124
92.0011
92.0249
91.9898
92.0136
92.0375
92.0262
92.0501
92.0626
92.9936
93.0175
93.0413
93.0062

CH sNP3
CH 7NP2
C2Hs0 4
ClI7N0 3
C3 HN4
C4HNP
C4H3N3
CSH02
CSH3NO
C5H5N2
C6H5O
C6H7N
C7H9
94
H2N20 4
H4N30 3
H6N40 2
CH 4N0 4
CH6NP3
CZH60 4
C3N3O
C3H2N4
C4N0 2
C4H2NP
C4H4N3
CSHP2
C5H4NO
C5H6N2
C6 HP
C6HSN
C7H 1O
95
H3N2 0 4

93.0300
93.0539
93.0187
93.0426
93.0202
93.0089
93.0328
92.9976
93.0215
93.0453
93.0340
93.0579
93.0705
94.0014
94.0253
94.0491
94.0140
94.0379
94.0266
94.0042
94.0280
93.9929
94.0167
94.0406
94.0054
94.0293
94.0532
94.0419
94.0657
94.0783
95.0093

160

Spectroscopic Data Chemistry


FM

HsN30 3
CHsN04
C3HNP
C3H3N4
C4HN0 2
C4H3NP
C4HSN3
CSHP2

95.0331
95.0218
95.0120
95.0359
95.0007
95.0246
95.0484

C~HsNO

95.0133
95.0371

CSH7N2
C6HP
C6 H9N

95.0610
95.0497
95.0736

C7H ll
96
H4N20 4

95.0861
96.0171
96.0073

C2NP
C 3NP2
C3H1N3O

95.9960

C3H4N4
C40 3
C4H2N01

96.0437
95.9847
96.0085

C4H4NP
C4H6N3

96.0324

CSHPl
CSH6NO
CsHsN2
C6HsO

96.0198

96.0563
96.0211
96.0449
96.0688
96.0575
96.0814

C6HION
C7H 1Z
Cs
97

96.0939
96.0000

CzHNp

97.0151

FM

FM

C3HNP2
C3H3NP
C3HSN4
C4H0 3
C4H3N0 2

97.0038
97.0277
97.0515
96.9925
97.0164

CgH2
99

98.0157

C2HNP2
Cif 3NP
ClIN0 3
C3H3NP2

99.0069

C4HsNp
C4H7N3

97.0402

CSHP2
CSH7NO
CSH9N2

97.0289
97.0528
97.0767

C6HP
C6HllN
C7H 13

97.0653
97.0892

C4H7NP
C4H9N3

97.1018

CgH
98

97.0078

C2NP2
C2H2NP
C3N0 3
C3H2N20 2

97.9991

CSHP2
CSH9NO
CSHllN2
C6 H ll O
C6H 13 N
C7H 1S
C7HN
CgH3

C3H4NP
C3H6N4

97.0641

98.0229
97.9878
98.0116
98.0355
98.0594

C3HSNP
C3H7N4
C4HP3
C4HsN02

99.0308
98.9956
99.0195
99.0433
99.0672
99.0082
99.0320
99.0559
99.0798
99.0446
99.0684
99.0923
99.0810
99.1049
99.1174
99.0109
99.0235

100

C4HP3
C4H4N02
C4H6NP
C4HgN 3

98.0003

CNP2

100.0022

98.0242

C1NP3
C2H2NPl
C2H4NP

100.0147
100.0386

CSH602
CsHsNO

98.0368

CP4
C3H2N03

100.0034

CSHIONl
C6H 1OO

98.0845

C6HI1N
C7H l4
C7N

98.0480
98.0719
98.0606
98.0732
98.0970
98.1096
98.0031

C3H4NPz
C3H6NP
C3HgN4
C4H40 3
C4 H6N02

99.9909

99.9796
100.0273
100.0511
100.0750
100.0160
100.0399

161

Mass Spectrometry

FM
C4HgNp
C4H1ON3

100.0637

CSHg02
CsHIONO

100.0524

CSHI2N2
C6 H1P
C6 HI4N
C6N2
C7H l6
C70

100.0876
100.0763
100.1001
100.0888
100.1127
100.0062
100.1253
99.9949

C7~N

100.0187

CgH4
101
CHN 40 2

100.0313

C2HNP3
C2H3NP2
C2HsN4O
C3H04
C3H3N03
C3HSNP2

101.0100
100.9987
101.0226
101.0464
100.9874
101.0113
101.0351

C3H7NP
C3H9 N4

101.0590

C4Hs03
C4H7N0 2
C4H9NP
C4H II N3
CSH902

101.0238

CsHllNO
CSHI3N2
C6 H 1P
C6 HISN
C6 HN2

101.0841

101.0829
101.0477
101.0715
101.0954
101.0603
101.1080
101.0967
101.1205
101.0140

FM

FM
C7HO
C7H3N

101.0027

C2HN0 4

102.9905

101.0266

103.0144

CgHs
102

101.0391

C2H3NP3
C2HsNP2
C2H7NP

CNP3
CH2N40 2
C2N04
C2H2NP3
C2H4NP2
C2H6N4O
C3HP4
C3H4N0 3
C3H6NP2
C3HgNp
C3H ION4
C4HP3
C4HgN0 2
C4H IONP
C4H I2N3
CSH 1OO2
CSHI2NO
CSHI4N2
CSN3
C6 H1P
C6NO
C6 H2N2
C7HP
C7H4N
CgH6
103
CHNP3
CH 3NP2

101.9940

103.0382
103.0621

C3HP4
C3HsN0 3

103.0031

C3H7NP2
C3H9NP

103.0508

C3HlIN4
C4HP3

103.0985

102.0542
101.9953

C4~N02

103.0634

102.0191

C4H lI NP
C4 H13 N3
CSH lI02
CSHI3 NO
CSHN 3
C6 HNO
C6 H3N2

103.0872

102.0178
101.9827
102.0065
102.0304

102.0429
102.0668
102.0907
102.0317
102.0555
102.0794
102.1032
102.0681
102.0919
102.1158
102.0093

C7HP
C7HsN
CgH7
104

103.0269
103.0746
103.0395

103.1111
103.0759
103.0998
103.0171
103.0058
103.0297
103.0184
103.0422
103.0548

CNP4
CH2NP3

103.9858

CH4 NP2
C2H2N04

104.0335
104.0222

103.0018

C2H4NP3
C2H6N30 2
C2HgNp
C3H40 4
C3H6N0 3

103.0257

C3HgNP1

102.1045
101.9980
102.0218
102.0106
102.0344
102.0470

104.0096
103.9983
104.0460
104.0699
104.0109
104.0348
104.0586

162

Spectroscopic Data Chemistry


FM

FM

C3HIONP

104.0825

C6 H0 2

104.9976

C3HI2N4
C4Hg03
C4H ION0 2

104.1063
104.0473

Cil 3NO
C6HSNl

C4H I2N2O

104.0950

CifsO
C7H7N

C4N4

104.0124

CSH I2 02
CsNp
C5H2N 3

104.0837

C60 2
C6H2NO

103.9898

C6H4N2
C7H4O

104.0375

C7H6N
CgHg
105

104.0501

CHNP4
CH 3NP3
CHsN40 2

104.9936

C2H3N04
C2HsN20 3
C2H7NP2
C2H9N4O

104.0712

107.0218

105.0453

C2H7NP3

107.0457

105.0340

C2H9NP2
C3HP4
C3H9N0 3

107.0695

105.0579

104.0011

CH 2NP4

106.0014

104.0249

CH4NP3
CH6N40 2

106.0253

C2H4N0 4
C2H6NP3
C2HgNP2
C2H 1ON4O
C3H60 4

106.0140

104.0626

105.0175
105.0413
105.0062
105.0300
105.0539
105.0777

C3HP4
C3H7N0 3
C3H9NP2
C3H 11 N 3O

105.0187

C4H90 3

105.0552

C4H 11 NO z
C4HN 4

105.0790

CsHNp
C SH3 N3

105.0215

105.0705

104.0262

105.0426
105.0664
105.0903

105.0202
105.0089
105.0328

C3HgN0 3
C3H ION20 2
C::4H IOO3
C4NP
C4H2N4
CSN0 2
CSH2Np
CSH4N3
C6 HP2
C6 H4NO
C6 H6N2

107.0570

CH 7NP2
C2HsN04

CgH9
106

104.0136

FM

107.0344
107.0583

C4HNP
C4H3N4
CSHN0 2

107.0120

CSH3NP
C5HSN3

107.0246

C6HP2
C6H5NO

107.0133

C6H7N2
C7HP
C7H9N

107.0610

CgH Ii
108

107.0861
108.0171

105.9929

CH4NP4
CH6NP3
CHgN40 2

108.0648

106.0167

C2H6N04

108.0297

106.0406

C2Hg NP3
C3HP4
C3N4O

108.0422

106.0491
106.0379
106.0617
106.0856
106.0266
106.0504
106.0743
106.0630
106.0042
106.0280

106.0054
106.0293
106.0532

C7H6O
C7Hg N

106.0419

CgH 10
107

106.0783

CH3NP4
CH sN30 3

107.0093

106.0657

107.0331

107.0359
107.0007
107.0484
107.0371
107.0497
107.0736

108.0410

108.0535
108.0073

C4NP2
C4H2NP
C4H4N 4

107.9960

CP3
CSH2NO z
CSH4Np
CS H6N3

107.9847

108.0198
108.0437
108.0085
108.0324
108.0563

163

Mass Spectrometry

C6 H40 2
C6H6NO
C6HgN2
C7HgO

108.0211

C9H3
112

111.0235
112.0022

110.0480

C2NP2
C3NP3
C3H2N30 2

CSHgN3
C6 H60 2

110.0719

C3H4N4O

112.0386

110.0368

C6 HgNO

110.0606

C40 4
C4H2N0 3

112.0034

C6HJON 2
C7 H JOO

110.0845

110.0355

108.0449

C4H4NP
C4H6N4

110.0594

108.0688

CSHP3

110.0003

108.0575

CSH4N 02
CSH6N P

110.0242

C7H JON
CgH J2

108.0814

C9
109

108.0000

CHsNP4
CHgNP3
C2H7N0 4

109.0249

C 3HNP

C7H J2N
C gH J4

110.0970

109.0151

C4HN ZOZ

109.0038

CgN

110.0031

C4H3NP
C4HsN4
CSH0 3

109.0277

C9 H2
111

110.0157
111.0069

CSH3N02
CsHsNp
CSH7N3

109,0164

C3HNP2
C3H3NP
C4HN03

C6HsOz

109.0289

108.0939

109.0488
109.0375

109.0515
108.9925
109.0402
109.0641

C6~NO

109.0528

C6H9Nz
C7H9O

109.0767

C7HJlN

109.0892

CgHJ3
C9H
110
CH6NP4
C3NP2
C3 H2N4O
C4N0 3
C4H2NP2

109.0653

FM

FM

FM

110.0732
110.1096

111.0308
110.9956

C4H3NPz
C4HsNp
C4H7N4

111.0195

C SHP3
CsH sN0 2

111.0082

CSH7Np
CSH9N 3
C6H70 2

111.0559

111.0433
111.0672
111.0320

111.9909
112.0147
111.9796

C4H4NP2
C4H6N P
C4HgN4
CSH403

112.0273

CSH6N 02
CSHgNp
CSH JON 3

112.0399

C6 Hg02
C6 HJONO
C6 H J2N Z
C7H J2 O
C7H J4N
C7N 2
CgH J6

112.0524

CgO
CgH2N

112.0511
112.0750
112.0160
112.0637
112.0876
112.0763
112.1001
112.0888
112.1127
112.0062
112.1253
111.9949
112.0187
112.0313

111.0446

C9 H4
113

111.0684

C2 HNPz

113.0100

111.0923

110.0229

C7HJ3N

111.1049

109.9878

CgHJS
CgHN

111.0109

C3HNP3
C3H3NP2
C3HSNP
C4H0 4
C4 H3N0 3

112.9987

109.9991

C6H9NO
C6H JJ N2
C7H JJ O

109.1018
109.0078
110.0328

110.0116

111.0798

111.0810
111.1174

113.0226
113.0464
112.9874
113.0113

Spectroscopic Data Chemistry

164

FM

114.1032

C6HI4N2
C6N3

114.1158

115.0171

115.0058

114.0093

C7HNO
C7H3N2

C7H 1P
C7H I6N
C7NO
C7H2N2
CgH lg

114.1045

CgHp

115.0184

114.1284

115.0422

113.9980

CgHSN
C9H7

114.0218

116

114.1409

C2NP4

115.9858

114.0106
114.0470

C2H2N30 3
C2H4N40 2
C3H2N04

116.0096

113.0140

CgHp
CgH4N
C9H6

113.1331

115

C3H 4NP3
C3H6N P2

116.0222

C3HgN4O
C4HP4
C4H6N03

116.0699

113.0351

C4H 7NP

113.0590

C4H9N4
CSHP3
CSH7N02

113.0829
113.0238

C SH 9N P

113.0715

CSHII N3
C6H90 2
C6H II NO
C6H 13 N2
C7H I3 O
C7H 1SN
C7HN 2
CgH I7

113.0954

113.0477

113.0603
113.0841
113.1080
113.0967
113.1205

114.0681
114.0919

114.0344

113.0027

C2HNP3

115.0018

113.0266

C2H3N40 2
C3HN04
C3H3N20 3
C3HSN302
C3H7N4O

115.0257

113.0391

114
C2NP3

113.9940

C2H2N40 2
C3N0 4

114.0178
113.9827

C3H2NP3
C3H4NP2

114.0065

C3H6NP
C4 H20 4
C4H4N0 3

114.0191

C4 H 6NP2

C4 HgNp
C4H ION4
CSH60 3
CSHgN0 2
CsHIONP

CSHI2 N3
C6H 1OO2
C6H I2NO

C6HN 3
C7H 1P
C7H17N

C4H sNP2

CgHO
CgH3N
C9 HS

FM

FM

114.9905
115.0144
115.0382
115.0621

115.1123
115.1362
115.0297

115.0548

116.0335
115.9983
116.0460
116.0109
116.0348

C4HgNP2
C4H ION3O
C4H I2N4

116.0586

116.0473

116.0825
116.1063

C4HP4
C4H sN0 3

115.0031
115.0508

114.0542

C4H 7NP2
C4 H9N P

CSHg03
CSH 1ON0 2

115.0746

CSH I2Np

116.0950

113.9953

C4H II N4

115.0985

CSHI4N3

116.1189

CSN4

116.0124

114.0429

CSHP3
CSH 9N 02

115.0395
115.0634

C6H 1P2

116.0837

114.0668

CsHIINp

115.0872

114.0907

CSH 13N 3
C6H 11 0 2
C6H 13NO

115.llll

C6H I4NO
C6HI6N2

116.1315

115.0759

C6NP

115.0998

C6 H,sN 2

115.1236

C6H2N3
C7H I6O

114.0304

114.0317
114.0555
114.0794

115.0269

116.0712

116.1076
116.0011
116.0249
116.1202

165

Mass Spectrometry

116.0136

CgH7N
C9H9

116.0375

118

CgHp
CgH6N

116.0262

CZH2NP4

118.0014

116.0501

C9 Hg

C2H4NP3
CZH6N4OZ
C3H4N0 4

118.0253

116.0626

C3H6N20 3
C3HgNP2
C3H 1ON4O
C4H60 4
C4HgN0 3
C4HION202
C4H I2N3O
C4H I4N4
CSH 1OO3
CSH 11N0 2
CSH I4N2O

118.0379

Cpz
C7HzNO
C7H4N2

115.9898

117

C2HN 20 4
C2H3NP3
C2HsN 40 2
C3H3N0 4
C3HSNP3
C3H7N32

116.9936
117.0175
117.0413
117.0062
117.0300
117.0539

C3H9NP
C4Hs04
C4H7N0 3

117.0777

C4H9NP2
C4HII N3O
C4H I3N4

117.0664

117.0187
117.0426
117.0903
117.1142

CSH90 3
CSH II N0 2
CSH 13 N2O

117.0552

CSHISN3
CSHN4
C6 H I3 0 2

117.1267

117.0790
117.1029
117.0202
117.0916

C6 H 1SNO

117.1154

C6 HNP
C6H3N3

117.0089

C7HOz
C7H3NO
C7HSN2

116.9976
117.0215
117.0453

CgHp

117.0340

117.0328

FM

FM

FM

CsNp
CSH2N4
C6H I40 2
C6N0 2

117.0579
117.0705

118.0491
118.0140
118.0617
118.0856
118.0266
118.0504
118.0743
118.0981
118.1220
118.0630
118.0868
118.1107
118.0042
118.0280
118.0994
117.9929
118.0167

CzHsNP3
CZH7NP2
C3HSN04

119.0331

C3H7NP3
C3H9N30 2

119.0457

C3HIINP
C4HP4
C4H9N03

119.0934

C4H II NP2
C4H I3 NP
CSH II 0 3
CSH I3N0 2
CsHNp
CSH3N4
C6HN01
C6H3NP
C6HSN3
C7HP2
C7HsNO
C7H7N2
CgHp
CgH9N

119.0570
119.0218
119.0695
119.0344
119.0583
119.0821
119.1060
119.0708
119.0947
119.0120
119.0359
119.0007
119.0246
119.0484
119.0133

i 19.0371
119.0610
119.0497
119.0736
119.0861

118.0406

C9 HII
120

C7HP2
C7H4NO
C7H6N z
CgH6 0

118.0054

C 2H4NP4

120.0171

118.0293

CZH6NP3
C1HgN4OZ
C3H6N04

120.0648

CgHgN
C9H 1O

118.0657

C6 H2NP
C6H4N3

118.0532
118.0419
118.0783

119

CZH3N 20 4

119.0093

120.0410
120.0297
120.0535

C3 HgNP3
C3HION 3OZ
C3H I2N4 O

120.0774

C4Hg04

120.0422

120.1012

166

Spectroscopic Data Chemistry


FM

FM

FM

C4H lON0 3
C4Hl2N202
C4N4O

120.0661

C6H3N0 2

121.0164

120.0899

C6 H 5N P

121.0402

120.0073

C6H7N3

121.0641

120.0786

C5NP2
C5 H zNp

119.9960

C7HP2
C7H7NO

121.0289

ClOH2
123

122.0157

C5H l2 0 3

121.0528

C 2H7NP4

123.0406

120.0198

Cll 14
C9N

122.1096
122.0031

C7H 9N z

121.0767

CZH 9NP3

123.0644

C5H4N4
C6 0 3

120.0437

CSH90

121.0653

C3H9N0 4

123.0532

119.9847

121.0892

CiINPz

123.0069

C6 H zN0 2

120.0085

CSHIIN
C9H 13

121.1018

123.0308

C6 H4NP

120.0324

121.0078

122.9956

C6H6N 3
C7H40 2

120.0563

CIOH
122

C4H3N4O
C5HN0 3
C5 H 3N Z02

123.0195

120.0211

CZH 6N z0 4

122.0328

123.0433

C7H6 NO

120.0449

122.0566

C7HsNz

120.0688

C2HsNP3
C2H lON4OZ

C5H5N30
C5H7N4

CsHsO

120.0575

CSHION

120.0814

C3HSN04
C3H lONz0 3

C9Hl2
C IO

120.0939

123.0672
123.0082

122.0453

C6 HP3
C6 H 5N OZ

122.0692

C6 H7NP

123.0559

C4H lOO4

122.0579

123.0798

120.0000

C4N 3OZ

121.9991
122.0229

C2H5N20 4

121.0249

C4H2NP
C5N0 3

C6H9N3
C7H70 2
C7H9NO

121.9878

C7H 11 N2

123.0923

C ZH 7N 30 3

121.0488

C 5H 2NPz

122.0116

123.0810

C2H9NP2
C3H7N04

121.0726

C5 H4NP

122.0355

CSHIIO
CSHl3 N

121.0375
121.0614

C3H ll N3OZ
C4HP4
C4 H 11 N0 3

121.0852

C5H6N 4
C6HP3
C6H4N02

122.0594

C3 H 9N P3

122.0242

C9H l5
C9HN
C 1oH3

121.0501

C 6 H 6N P

122.0480

124

121.0739

122.0719

124.0484

C4HN 4 O

121.0151

CzHsN20 4
C3NP2
C4N20 3
C4 H2N3OZ
C4 H4NP
C50 4

124.0386

121

122.0805

122.0003

C5HNP2

121.0038

C 5 H 3N P

121.0277

C6HSN3
C7H60Z
C7HsNO
C7H lONz

C5H5N 4
C6 H0 3

121.0515

CSHIOO

122.0732

120.9925

CSHl2N

122.0970

122.0368
122.0606
122.0845

123.0320

123.0446
123.0684

123.1049
123.1174
123.0109
123.0235

124.0022
123.9909
124.0147
123.9796

167

Mass Spectrometry

FM

FM

FM

CSH2N0 3

124.0034

C7H90 2

125.0603

CgNO

125.9980

CSH4Nz02
CSH6NP

124.0273

C7H II NO

125.0841

CgH2N2

126.0218

124.0511

C7H l3 N2

125.1080

C9H 1g

126.1409

124.0750

CgH I3 0

125.0967

C9HzO

126.0106

CgH1SN
CgHN 2

125.1205

126.0344

125.0140

C9H4N
ClO H6

125.1331

127

125.0027
125.0391

C3HNP3
C3H3N40 2
C4HN04

127.0018

124.0524

C9Hl7
C9 HO
C9 H3N

C4H3Nz03
C4HsN 30 2

127.0144

125.9940

C4H7NP
C5H30 4

127.0621

CSHgN4
C6H40 3

124.0160

C6H6N0 2

124.0399

C6 HgNzO

124.0637

C6HION3
C7Hg02
C7H lONO

124.0876
124.0763

CIOHS

C7Hl2Nz

124.1001

126

CgHlzO
CgH l4N

124.0888

CgN2
C9 H l6

124.0062

C90

123.9949

C9 H2N
C 1o H4

124.0187

124.1127
124.1253

124.0313

C3NP3
C3 H2N40 2
C4N04
C4H2N20 3

125.0266

126.0178
125.9827
126.0065

C4H4N,D2
C4H6NP

126.0304
125.9953

126.0542

C3HN 40 2

125.0100

C4 HN z0 3
C4H3N3 0 2
C4HsN4O

124.9987

CSHz04
CSH4N03
CSH6Nz02
CSHgN,D

125.0226
125.0464

C SHION4
C6H60 3

126.0907
126.0317

CSH04
CSH3N0 3

124.9874

126.0555

CsHsNz02
CSH7Np
CSH9N4
C6 HP3
C6 H7NOZ
C6 H9NzO
C6 H JI N3

125.0351

C6HgN02
C6H lON 2O
C 6Hl2N3

125

125.0113
125.0590

126.0191
126.0429
126.0668

126.0794
126.1032
126.0681

125.0829

C7H lOO2
C7H l2NO

125.0238

C7Hl4N 2

126.1158

125.0477

C7N3
CgH l4 0
CgH J6N

126.0093

125.0715
125.0954

126.0919

126.1045
126.1284

CsHsN0 3
C SH7N z02
CSH9NP

126.0470

127.0257
126.9905
127.0382
127.0031
127.0269
127.0508
127.0746

CSHIIN4
C6HP3
C6H9N0 2

127.0985

C6H II NzO
C6Hl3N3
C7H l1 0 2
C7H l3 NO
C 7H 1SN2

127.0872

C7HN 3
CgH1SO
CgH l7N

127.0171

CgHNO
CgH3N 2

127.0058

C9 H3O
C9HSN

127.0395
127.0634
127.1111
127.0759
127.0998
127.1236
127.1123
127.1362
127.0297
127.0184
127.0422

168

Spectroscopic Data Chemistry


FM

FM

C9H'9
CIO H7
128
C3NP4
C3H2NP3
C3H4N40 2
C4H2N04
C4H4N20 3
C4H6N30 2
C4HgN4O

127.1488
127.0548
127.9858
128.0096
128.0335
127.9983
128.0222
128.0460
128.0699

CSH404
CSH6N0 3

128.0109

CS HgN20 2

128.0586

128.0348

C9H6N
C,oH9
129
C3HNP4
C3H3N P3
C3HSN402

128.0501
128.0626
128.9936
129.0175

FM

CIO H9
130

129.0705

C3H2NP4

130.0014

C3H4NP3
C3H6NP2

130.0491

130.0253

C4H3N04
C4HsNP3
C4H7NP2
C4H9N4O

129.0062

CSHP4
CSH7N0 3

129.0187
129.0426

C4H4N04
C4H6NP3
C4HgNP2
C4H ION4O
CSH604
CSHgN0 3
CSH ION 202

CSH9N 202
CsHIlNp
CSH 13 N 4
C6H90 3

129.0664

CSH'2NP

130.0981

129.0903

130.1220

129.0790

CSH'4N4
C6H,003
C6H,2N02
C6H'4NP

129.0413
129.0300
129.0539
129.0777

130.0140
130.0379
130.0617
130.0856
130.0266
130.0504
130.0743

CsHIONP

128.0825

CSHI2N4
C6Hg0 3
C6H ION02

128.1063

C6H'2 NP
C6H'4N3
C6N4

128.0950

C7H'202
C7H,4NO
C7H'6N2

128.0837

C6H II NO l
C6H'3NP
C6HISN3
C6HN4
C7H I3 0 2

128.1076

C7 H 1SNO

129.1154

128.1315

C7H'7N2
C7HNP
C7H3N3

129.1393

C7H'402
C7H I6NO
C7N0 2

129.0089

C7H,gN 2

130.1471

CgH1P
CgH02
CgH'9N
CgH3NO
CsHsN2

129.1280

C7H2NP
C7H4N 3

130.0167

128.9976

CSH,gO

130.1358

129.1519

130.0054

C9HP
C9H7N

129.0340

CgHP2
CSH4NO
CSH6N 2
C9H6O
C9HSN

128.0473
128.0712
128.1189
128.0124

128.0011

C7NP
C7H2N3

128.0249

CgH'60

128.1202

CP2
CgH,gN
CgH2NO
C gH4N 2
Cq H20
C9H4O

127.9898
128.1440
128.0136
128.0375
128.1566
128.0262

129.1142
129.0552
129.1029
J29.1267
129.0202
129.0916

129.0328

129.0215
129.0453
129.0579

C6H'6N3
C6NP
C6H2N4

130.0603
130.0868
130.1107
130.1346
130.0042
130.0280
130.0994
130.1233
129.9929

130.0406

130.0293
130.0532
130.0419
130.0657

169

Mass Spectrometry

C,oH to

130.0783

131

FM

FM

FM

C3H7NP3
C3H9N40 2

133.0488

C4H7N0 4
C4H9NP3
C4HI\N 30 2

133.0375

133.1091

132.0422

C4H\3N 4O
CSH904

C3H6N30 3

132.0410

C3HgN40 2

132.0648

133.0726

C3H3N20 4
C3HSNP3
C3H7N40 2
C4HsN0 4
C4H7NZ03

131.0093

C4H6N04

132.0297

131.0331

C4HgNP3
C4H toN 30 2

132.0535
132.1012

C4H9NP2

131.0695

132.0661

CSH Il N0 3

133.0739

C4H"NP
CSHP4
CSH9N0 3

131.0934

C4H'2N40
CSHg04
CSH toN0 3

CSH\3N 20 2

133.0978

132.1138

CsH,sNP
CSHN40

133.1216

CsH"N 2OZ
CSH'3 N30

132.0786

C6 H\303
C6 H,sN0 2

133.0865

13l.l060

CSH'2N 202
C SH'4N30
CSH'6N4
CSN40

132.0899

131.0344

C6HNP2
C6H3NP

133.0038

C6HSN4
C7H0 3

133.0515

C7H3N0 2
C7HsNp
C7H7N 3

133.0164

CgHS02
CgH7NO
CgH9N 2

133.0289

C9H9O
C9H I\N

133.0653
133.1018

131.0570
131.0218
131.0457

131.0583
131.0821

132.0774

132.1377
132.0073

CsH,sN4
C6HI\03
C6H13 N0 2

13l.l298
131.0947

C6H'203
C6 H,4N 02
C6H'6NP

C6H,sNP
C6H'7N3
C6HN 3O
C6H3N4

13l.l185

C6NP2

131.9960

13l.l424

C6H2NP

132.0198

C6H4N4
C7H'602
C70 3
C7H2N02

132.0437

C7H4NP
C7H6N3

132.0324
132.02"11
132.0449

131.0708

131.0120
131.0359

132.1025
132.1264

132.1151
131.9847

C7H,s02
C7H,7NO
C7HN0 2
C7H3NP
C7HSN3

13l.l072
13 1.13 II

CgHP2
CgHSNO
CgH7N2

131.0133

CgH402
CgH6NO

131.0371

CgHgN2

132.0688

131.0610

C9 HgO

132.0575

C'OH\3
CI\H

C9HP
C9H9N

131.0497

134

131.0736

C9H,oN
Cto H '2

132.0814
132.0939

C,oH II

131.0861

CII

132.0000

C3H6NP4
C3 HgN30 3
C3 H toN40 2
C4HgN0 4

131.0007
131.0246
131.0484

132

C3H4NP4

132.0085
132.0563

133

132.0171

C3HSN 204

133.0249

133.0614
133.0852
133.0501

133.0151
133.1103
133.0277
132.9925
133.0402
133.0641
133.0528
133.0767
133.0892
133.0078
134.0328
134.0566
134.0805
134.0453

Spectroscopic Data Chemistry

170
FM

FM

FM

CSHII04
CSHI3 N0 3

135.0657

C6 H2 N0 3

136.0034

135.0896

C6 H 2N zOz

136.0273

CsHNP2
CSH3N 4O

135.0069

136.0511

134.0817

ClIN0 3

134.9956

C6H6N P
C6HgN4
C7H40 3

CSHI4NPz

134.1056

135.0195

CSN 30 Z

133.9991

C6 H3NPz
C6HSNP

CSH2Np
C6 H I4 0 3

134.0229

C6 H7N4
C7H30 3

135.0672

134.0943

C6N0 3

133.9878

C7 H sNO z

135.0320

C6 HzNPz

134.0116

C6H4NP
C6H6N 4

134.0355

C7H7N P
C7H9N3

C 7HZO}

134.0003

C4 HJON z0 3

134.0692

C~HI2NPz

134.0930

C 4H I4 N4O

134.1169

Cll JO O4
CSHIZ N0 3

134.0579

134.0594

135.0308

135.0433

ClIgNO Z
C7HgN2O

136.0750
136.0160
136.0399
136.0637

C7H IO N3
CgHgOZ
CgHIO NO

136.0876

135.0559

CgHIZN Z

136.1001

135.0798

C9 H 1ZO

136.0888

CgH70Z
CgH9NO

135.0446

C9 Hl4N

136.1127

135.0684

CgHllN Z
C9 H 1I O

C9N2
C lo H I6

136.0062

135.092.1
135.0810

CIOO

135.9949

135.1049

136.0187

135.1174

CIOHzN
C I1 H4

135.0109

137

135.0235

C3H9N Z04

137.0563
137.0881

135.0082

136.0524
136.0763

136.1253

C7 H 4NO z

134.0242

C7H6 NP
C7HgN3
C g H60 Z

134.0480
134.0368

CgHgNO

134.0606

C9 HI3 N
CIOH IS
CIO HN

CgHION Z
C9 H IOO

134.0845

C 11 H3

134.0732

136

C9 HIZN
C lo H I4

134.0970

C3 HgN Z0 4

136.0484

C3HIIN303
C4H II N04

134.1096

C3H ION30 3

136.0723

C4HN 4O Z

137.0100

CioN

134.0031

136.0961

CSHN Z0 3

136.9987

136.0610

CSH 3N 30Z

137.0226

CsHsNp
C6H0 4

137.0464

134.0719

CllH z
135

134.0157

C3HIZN40Z
C4H ION0 4

136.0848

C3 H7N Z04
C3H9N P3

135.0406

C4HI2Nz03
C4N 4O Z

135.0644

CSHIZ04

136.0735

C}HIIN 4 Oz
C 4H9N0 4

135.0883

CSN Z0 3

135.9909

135.0532

C sH zN 30 Z

136.0147

C4HIINz03

135.0770

CSH4Np

C4HI3N30Z

135.1009

C60~

136.0022

C6H3N0 3
C6HsN zOz

136.0313

137.0688

136.9874
137.0113
137.0351
137.0590

136.0386

C6 H7NP
C6 H 9 N 4

135.9796

ClI s0 3

137.0238

137.0829

171

Mass Spectrometry

C7H7N0 2
C7H9N P
C7HJl N3
CgH90 2

137.0477 . CgH I4N 2


137.0715 CgN 3

138.1158

C9 HNO

139.0058

138.0093

C9 H3N 2
C 1o H l9

139.0297
139.0184

137.9980

C10HP
C 1oH5N

139.0422

138.0218

C 11 H7

139.0548

138.1409

140

138.0106
138.0470

C4NP4
C4HzNP3
C4H4N40Z
C5HzN04

137.0954

C9 H I4 O

138.1045

137.0603

C9H'6N
C9NO

138.1284

CgHJlNO
CgH 13 N Z

137.0841

C9H 13 O
C9 Hl5N
C9 HN Z

137.0967
137.0140

C9HzN z
C10H Ig
ClOHzO
C 1oH4N

C 1oH l7

137.1331

C lI H6

ClOHO
ClO H3N
C 11 H5

137.0027

139

137.0266

C4HNP3
C4H3NPz
C5HN0 4

139.0018

C5H3NP3
C5H5NPz

139.0144

137.1080
137.1205

137.0391

138

138.0641

138.0344

139.0257
138.9905

C3H1ONz04
C4NP3
C4HzN4OZ

138.0178

C5N04

137.9827

C5H7NP
C6H30 4

139.0621

C5HzNP3
CSH4N30Z
CSH6N4O

138.0065

C6HsN0 3

139.0269

138.0304

C6 H7N ZOZ
C6H9N P

139.0508

C6Hz04
C6H4N0 3

137.9940

138.0542
137.9953
138.0191

C6 H6NPz
C6HgNp
C6H lON4

138.0429

C7HP3
C7HgNO Z
C7H 1ON zO

138.0317

C7H1ZN 3
CgH100 Z
CgH l2NO

138.1032
138.0681

138.0668
138.0907
138.0555
138.0794

138.0919

FM

FM

FM

139.0382
139.0031

139.1488

139.9858
140.0096
140.0335
139.9983

C5H4NZ03
C5H6N 30Z

140.0222

C5HgNp
C6H40 4
C6H6N0 3

140.0699

C6 HgNPz
C6 H lON30

140.0586
140.1063

140.0460
140.0109
140.0348
140.0825

C6 HlIN4

139.0746
139.0985

C7HP3
C7H9N OZ

139.0395

C6HIZN4
C7Hg03
C7H lONO z
C7H1ZN zO
C7H'4N 3

139.0634

C7N4

140.0124

C7H'IN zO
C7Hl3 N3

139.0872

CgH l2 0 Z
CgH l4NO

140.0837

CgH110 Z
CgH l3 NO
CgH 1S N2

139.0759

140.1315

139.1236

CgH l6N Z
CgNp
CgHZN3

CgHN 3
C9H l5 O
C9 H'7N

139.0171
139.1123

C9 H l6 O

C90 Z

140.1202
139.9898

139.1362

C9 HlgN

140.1440

139.1111
139.0998

140.0473
140.0712
140.0950
140.1189

140.1076
140.0011
140.0249

Spectroscopic Data Chemistry

172

FM

FM

142.0054

14 l.l 644

C9HP2
C9H20N
C9 H4NO

141.0340

C9H6Nz

142.0532

141.0579

C 1oH22

142.1722

141.0705

CIOHP
CIOHgN

142.0419

C4H2NP4
C4H4N30 3

142.0014
142.0253

CllH IO
143

142.0783

C4H6NP2
CSH4N04

142.0491

C4H3NP4
C4HsNP3

143.0093

CSH6NP3
CSHgN30 2

142.0379

C4H7NP2
CsHsN04

143.0570

CSH ION4O
C6 H60 4

142.0856

C6HsN0 3
C6H lON20 2
C6H l2N3O

142.0504

C6Hl4N4
C7H lOO3

142.1220

CSH7NP3
CSH9NP2
CSH Il N40
C6H70 4
C6H9N0 3
C6H Il N20 2

143.0457

142.0868

14 l.l 029

C7H l2N0 2
C7H l4NZO

141.1267

C9 H2NO

140.0136

C9H4N2
C lO H20

140.0375

C lO H4 O

140.0262

ClO H6N

140.0501

C9 H3NO
C9 HsNz
ClOH21
CIOHP
C 1oH7N

C11HS
141

140.0626

C ll H9

C4HNP4
C4H3N30 3

140.9936
141.0175

C4HsN40 2
CSH3N04
CsHsNP3
CSH7N302

141.0413

140.1566

141.0062
141.0300
141.0539
141.0777

C6 HP4

141.0187

C6H7N0 3
C6H9N20 2
C6H ll N3O
C6Hl3N 4
C7H90 3
C7H lI N0 2

141.0426

C7HN 4
C 7H l3 O Z
CgH1SNO
CgHl7N 2
CgHNp
CSH3N3

141.0215
141.0453

142

CSH9N4O

C7H l3 N ZO
C 7H1SN 3

FM

141.0664
141.0903
141.1142
141.0552
141.0790

141.0202
141.0916

142.0140
142.0617
142.0266
142.0743
142.0981

142.0293

142.0657

143.0331
143.0218
143.0695
143.0934
143.0344
143.0583
143.0821
143.1060
143.1298

142.1107

C6Hl3 NP
C6HlSN4
C7H Il O3

C7H l6N3

142.1346

C7H 13NO Z

143.0947

C7NP
C7H2N 4

142.0042

C7H 1SNP
C7H l7N 3

143.1185

142.0630

142.0280

142.0406

CgHN0 2
CSHl9N2

143.0007

142.1358

CgH3Np

143.0246

142.1233

141.0089

CgN02

141.9929

141.0328

142.1471

C9H 1P

141.1280

C9 HOz

140.9976

C9 Hl9N

141.1519

C9H 1SO

143.1424
143.0120

141.1393

Cgl-llgN2
CgH2Np
CgH4N3

143.0708

C7HNP
C7H3N 4
CgH 1S0 2
CgH l7NO

142.0994

CSH l40Z
CgH l6NO

141.1154

142.1597

142.0167

143.0359
143.1072
143.1311
143.1549

173

Mass Spectrometry

CgH5N 3
C9 HlP
C9H30 2

143.0484

C9H2lN
C9H5NO

143.1675

C9H7N2

143.0610

CloHP
CIOH9N

143.0497

143.1436
143.0133
143.0371

143.0736

CllH ll
144

143.0861

C4H4NP4
C4H6NP3
C4HgN40 2
C5H6N04

144.0171

C5HgNP3
C5H ION30 2

144.0535

C5Hl2NP
C6Hg04
C6HION0 3

144.1012

144.0410
144.0648
144.0297
144.0774

FM

FM

FM

C7H3NP
C7H5N4

145.0277
145.1229

144.0324

CgHl7 0 2
CgH03

144.0563

CgH l9NO

145.1467

C9H20O
C9H4 0 2

144.1515

145.0164

144.0211

CgH3N02
CgH5Np

C9H6NO
C9HgN2
CIOHgO

144.0449

CgH7N3

145.0641

144.0688

C9 HPz
C9 H7NO

145.0289

CIOHION
C ll H l2

144.0814

C9H9N2
C IOH9O
CIOHll N

145.0767
145.0653

C ll H13

145.1018

ClzH
146

145.0078

C4H6NP4
C4HgN30 3

146.0328

CgHlgNO
CgH2N0 2

144.1389

CgH20N2
CgH4Np
CgH6N3

144.1628

C lZ
145
C4H5NP4
C4H7NP3
C4H9N40 2

144.0085

144.0575
144.0939
144.0000
145.0249
145.0488
145.0726

145.0515
144.9925

145.0402

145.0528

145.0892

145.0375

144.0661

C5H7N04
CSH9NP3

C6HI2N202
C6HI4NP
C6HI6N4

144.0899

CSH ll N30 2

145.0852

C4H lON40 2
CSHgN04

146.0453

144.1138

CSHI3N40

145.1091

CSH ION z0 3

146.0692

144.1377

146.0930

C6NP
C7H l2 0 3

C6 HP4
C6H ll N0 3

145.0501 ' CSH l2NPz

144.0073

146.1169

144.0786

145.0978

C7H l4N02

144.1025

C6HI3NzOz
C6H I5N3O

CSH l4N40
C6H lOO4
C6H I2N0 3

C7 H I6N2O

144.1264

C 7NPz

143.9960

C7H lgN 3

144.1502

C6HI7N4
C6HNP
C7H I3 0 3

145.1455

C7HzNp
C7H4N4
CgH l6 0 2

144.0198

Cg0 3

143.9847

144.0422

145.0614

145.0739
145.1216

146.0566
146.0805

146.0579
146.0817
146.1056

145.0151

C6HI4N202
C6HI6N P

145.0865

C6 NPz

145.9991

C6HlgN4
C6H2N4O

146.1533

C7H l4 0 3
C7H l6 NO z

146.0943

C7H lS NO z

145.1103

144.0437

C7Hl7NP

145.1342

144.1151

C7HNP2
C7H l9N3

145.0038
145.1580

146.1295

146.0229
146.1182

Spectroscopic Data Chemistry

174
FM

FM

C7N0 3

145.9878

C7H 1S 0 3

147.1021

C7H 1g N2 O

146.1420

C7H I7N0 2

147.1260

C7H 2NP2

146.0116

C7HN0 3

146.9956

C7H 4NP

146.0355

C7H6N4
CgH lg02

146.0594

C7H3NP2
C7 H sNp

C7H7N4
CgHP3
CgHSN0 2

CgHP3
CgH4N 02

146.1307
146.0003

FM

C6H4N4O
C7H I6 0 3

148.0386
147.9796

147.0195

CP4
C7H2N0 3

147.0433

C7H4N20 2

148.0273

147.0672

C7 H6N P
C7HgN4

148.0511

147.0082

148.1100
148,0034

148.0750

147.0320

CgH40 3

148.0160

147.0559

CgH6N 02
CgHgN 20

148.0399

146.0719

CgH7Np
CgH9N3

C9 H60 2

146.0368

C9 H70 2

147.0446

148.0876

C9 HgNO
C9H ION 2

146.0606

147.0684

148.0524

146.0845

C9 H9NO
C9 HlIN2

CgH ION 3
C9 Hg02
C9 H 1ONO

CIOHIOO
CIOH I2N

CIOH1P
C 1OH 13N

147.0810

146.0970

147.1049

C9 HI2N2
C IOH I2O

148.0888

C lI H I4

146.1096

CIIH 1S

147.1174

CIO H I4N

148.1127

C11N
C I2 H2

146.0031

C11HN
C I2 H3

147.0109

148.0062

147.0235

ClON2
C II H 16

147.9949

146.0242

CgHgNp
CgHgN3

146.0480

146.0732

146.0157

147.0798

147.0923

148

147
C4H7NP4
C4H9N30 3

147.0406

C4HgNP4

148.0484

C1P
C II H2N

147.0644

C4HION303

148.0723

C I2 H4

C4H II N40 2

147.0883

CSH9N 04
CSHIIN203
CS H 13N 302

147.0532

C4HI2N402
CS H ION 04

148.0961
148.0610

147.0770

CSHI2N203

148.0848

149
C4H9N 20 4
C4H II N 30 3

147.1009

148.1087

CSH 1SN 4O
C6 H II 0 4

147.1247

CSHI4N302
CSHI6N 40

C6H I3 N0 3
C6HISNz02
C6 HI7N3O

147.0896

CSNP2
C6H I2 0 4

C6HNPz
C6H3NP

147.0657

147.0069

C6H I4N0 3
C6HI6N202
C6N 20 3

147.0308

C6 H2N 3OZ

147.1134
147.1373

148.0637

148.0763
148.1001

148.1253
148.0187
148.Q313
149.0563
149.0801
149.1040

148.1325

C4HI3N402
CSH 11 N04

148.0022

C5HI3N203

149.0927

148.0735
148.0974

CSHISN302
CS HN 40 Z
C6 H I3 0 4

149.1165

148.1213
147.9909
148,0147

C6H I5N0 3
C6 HN 20 3

149.0688

149.0100
149.0814
149.1052
148.9987

175

Mass Spectrometry

C6H3N P2
C6H5N 4O
C7H04

149.0226

C 7H3N0 3

149.0113

C7H5NPz
C7H7NP
C7H9N 4

149.0351

149.0464
148.9874

149.0590
149.0829

CgHP3
CgH7N 02

149.0238

CgH9Np

149.0715

CgHI\N 3
C9 H90 2

149.0954

C9HI\NO
C9 HI3 N 2

149.0841

C IO H l3 O

149.0967

CIO H l5N
CIO HN 2
CI\H I7
CI\HO
CI\ H3N

149.0477

FM

FM

FM
C6H4NP2
C6H6N P

150.0304

C6 H7N4O

151.0621

150.0542

C7HP4
C7H5N0 3

151.0269

C7HP4
C7H4N0 3

149.9953

C7H6NP2
C7HgNp
C7H 1ON4

150.0429

C gH60 3
CgHgN0 2

150.0317

CgH'ONp
CgH I2N 3

150.0794

150.0191
150.0668
150.0907
150.0555

151.0031

C7H7NP2
Cll 9NP
C7H 11 N 4

151.0508

CgH70 3
CgH9N02

151.0395

CgH,1Np
CgH\3N 3

151.0872

151.0746
151.0985
151.0634
151.1111

C9HI\02
C9H I3NO
C9 HI5N2

151.0759

C9HN 3
C IOH l5 O
C 1o H l7 N

151.0171

151.0058

149.9980

CIOHNO
C 1oH3N 2

150.0218

C 11 H l9

151.1488

C 11 H I8

150.1409

C 11 H 3O

151.0184

150.0106

C 11 H5N
C I2 H7
152

151.0422

150.0641

CI\Hp
C 11 H4N
C l2 H6

150.0879

151

152.0797

150.1118

C4HIIN204
C4H\3NP3
C5H I3 N0 4

C4Hl2N204
CSN20 4
CSH 2N 30 3

152.0335

151.0018

C5H4N40 2
C6 HzN04

151.0257

C6H4N 20 3

152.0222

150.9905

152.0460

151.0144

C6 H6N 30 2
C6 HSN 4O

151.0382

C7H40 4

152.0109

150.1032

C9H 1OO2
C9 H I2NO

150.0681
150.1158
150.0093

149.1205

C9HI4N2
C9N 3
C IO H I4 O

149.0140

C 1OH l6N

150.1284

149.1331
149.0027

CloNO
CIO H2N2

149.0266

C l2 H5
150
C4H ION 20 4

149.0391

C4Hl2N303
C4HI4N402
C SH l2N0 4

150.0766

C5HI4Nz03

150.1005

C5NP3
C5H2NP2
C6H I4 0 4
C6N0 4

149.9940

C5HNP3

150.0178

C5H3N40 2

150.0892

C6H2NP3

150.0065

C6HN0 4
C6 H3N20 3
C6H5N 30 2

149.0603
149.1080

149.9827

150.0919

150.1045

150.0344
150.0470
151.0719
151.0958
151.0845

151.0998
151.1236
151.1123
151.1362
151.0297

151.0548

151.9858
152.0096
151.9983

152.0699

176

Spectroscopic Data Chemistry


FM

FM

FM

C7H6 N03

152.0348

C 7 H7N0 3

153.0426

C7HgN0 3

154.0504

C7HgNPz
C7H IO N3 O

152.0586

C7H9NPz

153.0664

154.0743

152.0825

153.0903

C7H 1ZN 4

152.1063
152.0473

153.0552

C7H I4N4
C gH IO O3

154.1220

CgHg0 3

C7H Il N3O
C7H I3 N4
CgH90 3

C7H lO NzOz
C7H 1ZNP

CgH1ONO Z

152.0712

153.0790

CgH I2NO Z

154.0868

CgH1ZNp
C gH I4N 3
CgN 4

152.0950

153.1029

152.1189

CgHIlNO Z
C9HI3 NP
CgH I5 N3

153.1267

CgH I4Np
CgH I6N3

154.1346

152.0124

CgHN4

C9H 1Z OZ

152.0837

C9H I3 OZ

153.0202
153J)916

CgNp
CgHZN4

154.0042
154.0280

C9H I4 NO

152.1076

C9H I5 NO

153.1154

154.0994

C9H I6N z

152.1315

C9H I7N z

153.1393

C9 HI4 0 2
C9 H I6NO

C9N zO

152.0011

C9HNP

153.0089

C9NOz

154.1233
153.9929

C9HzN 3

152.0249

153.0328

C9HIgN2

154.1471

C IO H I6 O
C IO O2
CIO H lg N

152.1202

C9H3N3
C IOH I7 O

153.1280

C9H2NP

154.0167

CloHO z
C 1OH I9N
CIOH3NO
C IOH5N z
C II H21

152.9976

C9H4N3
C1OHIgO

154.0406

C 1oH2O Z

154.0054
154.1597

152.0501

CIIHP
C II H7N

153.0340

CIO H20N
C 1OH4NO
C 1oH6N2

153.0579

C 11 Hz2

154.1722

152.0626

C 1z H9

153.0705

C II H60

154.0419
154.0657

CIOHzNO
CIOH4N2
C II H20

151.9898
152.1440
152.0136
152.0375
152.1566

153.1142

153.1519
>,

153.0215
153.0453
153.1644

CIIHP
C II H6N
C I2 Hg
153

152.0262

C5HN Z0 4

152.9936

C5H2NP4

154.0014

C5H3NP3

153.0175

154.0253

C5H5N 4OZ

153.0413

C6H3N04

153.0062

C6H5N P3
C6H 7NPz

153.0300

C5H4NP3
C5H6 N40 2
C6H4N0 4
C6H6N20 3
C6HgN3OZ

C6H9NP
C7H50 4

153.0777

154

153.0539
153.0187

C6HIONP
C7H60 4

C11HgN

154.0981
154.0630
154.1107

154.1358

154.0293
154.0532

C1zH 1O
155

154.0783

C5H 3N P4
C5H 5N P3

155.0093

154.0140
154.0379

C5H 7NPz

155.0570

154.0617

C6H5N04
C6 H7N20 3

155.0218

154.0856
154.0266

C6 H9N30Z

155.0695

154.0491

155.0331

155.0457

177

Mass Spectrometry
FM
C6 HlINP
C7H70 4

155.0934

Cll9N0 3

155.0583

C7H lI NP2
C7H l3NP
C7H 1S N4

155.0821

CgH 11 0 3
CgH l3N02

155.0708

CgH1SNp
CgH17N3
CgHNp
CgH3N4
C9H1S0 2
C9HI 7NO
C9HN02
C9Hl9N2
C9H3N2O
C9HSN3
C 1oH I9O
C IO H30 2
C 1O H21 N

155.0344

155.1060
155.1298
155.0947
155.1185

156.0535

C l3

156.0774

157

C6H l2N4O
C7Hg04
C7H lON0 3

156.1012

157.0249

156.0661

CsHsNP4
CSH7NP3
CSH9N402

156.0899

C6H7N04

157.0375

156.1138

C6H9NP3
C6HIIN302
C6 H l3 N4O
C7H90 4
C7H lI N0 3
C7H 13N 20 2

157.0614

C7H 1S N3 O
C7H l7N4
C7HN 4O

157.1216

C7Hl2N202
C7H l4NP
C7Hl6N4

156.0422

156.1377
156.0073
156.0786

155.0120
155.0359

CgH l6Np

156.1264

155.1072

CgNP2
CgH 1gN3
CgH2Np
CgH4N4
C9H l6 0 2

155.9960

155.1311
155.0007
155.1549
155.0246
155.0484
155.1436
155.0133
155.1675
155.0371

ClIHP
C lI H9N
C I2 H 11

155.0497

155.0610
155.1801
155.0736
155.0861

156

156.0171
156.0410
156.0648
156.0297

FM

C6HgNP3
C6 H lON30 2

C7NP
CgH l2 0 3
CgH l4N0 2

155.1424

C1oHsNO
CIO H7N2
C II H23

CSH4NP4
CSH6N P3
CSHgN40 2
C6 H6N0 4

FM

CP3
C9H 1gNO
C9H2N0 2
C9H20N2
C9H4NP
C9H6N 3
C IO H20O
C IO H40 2
CIO H22N
C 1O H6NO
CIO HgN2
C 11 H24
CIIHgO
ClIHION
C 1z H I2

156.1025

156.1502
156.0198
156.0437
156.1151
155.9847
156.1389
156.0085
156.1628
156.0324
156.0563
156.1515
156.0211
156.1753
156.0449
156.0688
156.1879
156.0575
156.0814
156.0939

156.0000

157.0488
157.0726

157.0852
157.1091
157.0501
157.0739
157.0978
157.1455
157.0151

CgH 1P3
CgH1S N0 2
CgHl7Np

157.0865

CgHNP2
CgH19N3

157.0038

CgH3N~O
CgHSN4
C9H I70 2
C9H03

C9 H I9NO
C9H3N0 2

157.1103
157.1342
157.1580
157.0277
157.0515
157.1229
156.9925
157.1467
157.0164

C9H21N2
C9 HSNP
C9H7N3
C IO H21 O

157.1706

CIOHsOz
CIO H23 N

157.0289

157.0402
157.0641
157.1593
157.1832

178

Spectroscopic Data Chemistry

FM

FM

FM

C IO H7NO

157.0528

C9H4N0 2

158.0242

C 1O H9Nz

157.0767

C9 H 2ZN z

158.1784

C11HP

157.0653

158.0480

CIIH11N
C 1z H I3 _

157.0892

158.0719

157.1018

C9H6N P
C9HgN3
C lO Hz2 O

Cl"~3NP2
CgHZ1 N3
CgHSNp
CgH7N 4

158.1671

C9H I90 2

159.1385

C I3 H

157.0078

C lO H6OZ

158.0368
158.0606

C9HP3
C9Hz1 NO

159.0082

158.0328

ClOHgNO
ClO H lON2

158.0845

C9H sNO z

159.0320

158.0732

C9H7NP
C9H9N3

159.0559

ClOHPz
ClO H9 NO

159.0446
159.0684

158
CSH6N204
CSHgN30 3
CSH lON 4OZ

158.0566
158.0805

159.0195
159.1737
159.0433
159.0672

159.1624

C6HgN04
C6H lONz0 3

158.0453

CIIHlOO
C II H l2 N
C 1z H l4

158.0692

C l2N

158.0031

C6HJ2N302
C6H l4N4O
C7H 1OO4

158.0930

C13 H2

158.0157

ClOHIIN z

159.0923

158.1169

159

159.0810

158.0579

159.0406

C7H JZ N03
C 7H J4NP2
C7Hl6N3O

158.0817

CSH7NP4
CSH9N30 3

CIIHIIO
C 11 H13 N

159.0644

C I2 H 1S

159.1174
159.0109

158.1056

158.0970
158.1096

159.0883

158.1295

CSH lI N 402
C6H9N0 4 .

159.0532

C1ZHN
C13 H3

C7N 30 2

157.9991

C6HIINz03

159.0770

160

C7H 1gN4

158.1533

C7HzN 4O

158.0229

C6Hl3N302
C6H 1SN 4O

159.1009
159.1247

CSHgNP4
CSHION303

CgH l4 0 3

158.0943

C7H lI 0 4

159.0657

CgHJ6N 02
CgN0 3

158.1182

C7H l3 N0 3

159.0896

157.9878

159.1134
159.1373

159.0798

159.1049

158.0235
160.0484
160.0723
160.0961

CgH,gNp
CgH2N2OZ

158.1420

C7HJSN202
C7HJ7N P

158.0116

C7HN 30 2

159.0069

CSHJZN40Z
C6H lON04
C6HJ2N203
C6Hl4NP2
C6H J6NP

CgH20N3

158.1659

C7H I9N4

159.1611

C6N 4OZ

160.0022

CgH4Np
ClI6 N4

158.0355

C 7H3NP
CgH 1S 0 3

159.0308

C7H 1Z0 4

160.0735

158.0594

159.1021

C7H I4 N0 3

160.0974

CiIJgOz

158.1307

CgH I7N0 2

159.1260

C 9HP3

158.0003
158.1546

CgHN03

158.9956

C7HJ6 NP2
C7N 20 3

160.1213

CgH I9N ZO

159.1498

C7H 1gN 3 O

160.1451

C9H20NO

160.0610
160.0848
160.1087
160.1325

159.9909

179

Mass Spectrometry

160.0147

159.9796

C6H,sNPl
C6H'7N40
C6HN 4OZ
C7H 13 0 4
C7H,sN0 3

160.1338

C7H'7N ZOZ

160.0034

C7HNP3
C7H'9NP

C7H2NP2
C7H20N4

160.1690

C7H4NP

160.0386

CgH'603
Cg0 4
CgH,gNO Z
CgHZN03

160.1100

CgHZONp
CgH4NP2
CgH6Np
CgHgN4

160.1577

C9H 20O Z

160.1464

C9H40 3
C9H6NOZ
C9HgNp
C9H lON3

160.0160

160.0273
160.0511
160.0750

160.0399
160.0637
160.0876

CIOHgOz
CIOHIONO
C lOH l2Nz

160.0524

CllH1ZO

160.0888

C ll H l4N
C ll N2

160.0062

C 1zH l6

160.1253

C,p
C l2 HzN
C'3 H4

159.9949

160.0763
160.1001
160.1127

160.0187
160.0313

161

C7H3NPz
C7H5N4O
CgH l7 0 3
CgH04
CgH l9NOZ
CgH3N0 3
CgHSNPz
CgH7Np
CgH9N4
C9H50 3
C9 H7NOZ
C9 H9NP
C9 HllN3
C 1oH9OZ

CIOHllNO
C IO H'3N Z
CllH1P
CllH,sN
CllHN Z

CSH9NP4
C5Hll N30 3

161.0563

C5Hl3N402
C6 H lI N04
C6 H'3 N 203

161.1 040

C'ZH I7
C1zHO
C,zH3N
C l3 H5

161.0688

162

161.0927

C5H,oN 20 4

161.0801

FM

FM

FM

161.1165
161.1404
161.0100
161.0814
161.1052
161.1291
160.9987
161.1529
161.0226
161.0464
161.1178
160.9874
161.1416
161.0113
161.0351
161.0590
161.0829
161.0238
161.0477
161.0715
161.0954
161.0603
161.0841
161.1080
161.0967
161.1205
161.0140
161.1331
161.0027
161.0266
161.0391
162.0641

CsH,zN 30 3
CSH'4N40Z

162.0879

C6 H,zN04

162.0766

C6 H'4N 203

162.1005

C6H'6N 30Z

162.1244

C6NP3
C6H,gN4O

161.9940

C6H 1NPz

162.0178

C7H'404
C7 H,6 N03
C7N04

162.0892

C7H,gN 2OZ

162.1369

C7H zN z0 3

162.0065

C7H4NPz

162.0304

C7H6N P
CgH,g03

162.0542

CgHP4
Cg H4N0 3

161.9953

CgH6NPz
CgHgNp
CgH lON4
C9 H60 3
C9 HgNO Z

162.0429

C9 H,oNP
C9 H'2 N3

162.0794

CIOHIOO Z
C IO H,2NO
C II H l4 0
C ll H'6N

162.0681

CIINO
C II H2N2
C'2 H ,g

162.1118

162.1482

162.1131
161.9827

162.1256
162.0191
162.0668
162.0907
162.0317
162.0555
162.1032
162.0919
162.1045
162.1284
161.9980
1620218
162 1409

Spectroscopic Data Chemistry

180

FM
C I2 HP
C I2 H4N
C13 H6

FM

FM

162.0106

C 11 H I7N

163.1362

C IOH I4NO

164.1076

162.0344

C11HNO
C 11 H3N z
C I2 H I9
C1zHP

163.0058

C IOH'6N2
CIONP
C IO HzN 3

164.1315

162.0470

163
CSHIIN z0 4
CSH'3 N 303

163.0719

CsH,sN 4OZ
C6H I3 N04

163.1196

163.0958
163.0845

C6 H,sN z0 3
C6 H'7 N 30Z
C6HN30 3

163.1083

C6H3N40 2
C7 H 1S 0 4
C7H I7N03
C7HN04
C7H3N20 3
C7HsN30 2
C7H7NP
CgH30 4
CgHSN0 3

163.0257

163.1322
163.0018
163.0970
163.1209
161.9905
163.0144
163.0382
163.0621
163.0031
163.0269

CgH7NP2
CgH9Np
C gH II N4

163.0508

C9HP3
C9H9N0 2

163.0395

163.0746
163.0985
163.0634

C9H'I N20
C9HI3 N3
C IO H 11 0 2
C 1OH 13 NO

163.0872

CIOH1sN z
CIO HN 3

163.1236

C II H I5 0

163.1123

163.1111
163.0759
163.0998
163.0171

C'zHsN
C'3 H7
164

163.0297
163.1488
163.0184
i63.0422
163.0548

CsH,zN 20 4
CSH'4 N 303
CS H'6N402

164.0797

C6H,4N 04
C6HI6N203
C6NP4
C6 HzN 30 3
C6 H4N 4OZ
C7H I6 0 4
C7H2N04
C7H4N20 3
C7H6N30 2
C7HgNp

164.0923

164.1036
164.1275
164.1162
163.9858
164.0096
164.0335
164.1049
163.9983
164.0222
164.0460
164.0699

Cg HP4
Cg H6N0 3

164.0109

CgHgNPZ
CgH,oNp

164.0586

CgH'2N4
C9Hg0 3
C9 H IONO z

164.1063

C9HI2NP
C9HI4N3
C9N4
C IO H 1Z 0 2

164.0950

164.0348
164.0825
164.0473
164.0712
164.1189
164.0124
164.0837

164.0011
164.0249

C II H I6 0
C II 0 2

164.1202

CIIH,gN
C II H2NO
C II H4N2
C'2 H20
C'2 H40
C'2 H6N
CI3 Hg
165
CSH 13N204

164.1440

CsH,sN30 3
C6 H,sN0 4
C6HNP4
C6H3N30 3
C6 HSN402
C7H3N0 4
C7HsNP3
C7 H7N 30Z
C7H9NP
CgHP4
CgH7N0 3
CgH9N 20 2
CgH II N30
CgH I3N4
C9H90 3
C9HII N02
C9 H I3 N2O

163.9898
164.0136
164.0375
164.1566
164.0262
164.0501
164.0626
165.0876
165.1114
165.1001
164.9936
165.0175
165.0413
165.0062
165.0300
165.0539
165.0777
165.0187
165.0426
165.0664
165.0903
165.1142
165.0552
165.0790
165.1029

181

Mass Spectrometry
FM

FM

C9 HISN3

165.1267

C9 HN4
C IO H 1302

165.0202

CIOHlsNO

165.1154

CloHI7N2
CIOHNP
CIO H3N 3

165.1393

C9H2N4
C IOH I4 0 2

165.0089

C IO H I6NO

165.0328

C ION0 2

C II H I70

165.1280

C 11 H0 2
C II H 19N

164.9976

CIO H 1SN 2
CIOH2NP
CIO H4N3

C II H3NO

165.0215

C II HSN2
C I2 H21

165.0453

165.0916

165.1519

C9 HI4NP
C9HI6N3
C9N 3O

166.1107
166.1346
166.0042
166.0280
166.0994

FM

C9 H1P3
C9HI3 N0 2
C9HISNP
C9HI7N 3

167.0708
167.0947
167.1185
167.1424
167.0120

166.1233

C9HNP
C9H3N4

165.9929

C IO H 1S0 2

167.1072

166.1471

C IO H I7NO

167.1311

166.0167

C IO HN0 2
CIO HI9N2

167.0007
167.0246

166.0406
166.1358

167.0359

167.1549

166.0054

165.1644

CIIH1SO
C II H20 2
C II H20N

CIOH3NP
CIO HSN 3

166.1597

C II H I9 0

167.1436

C I2 HP
C I2 H7N

165.0340

C II H4NO

166.0293

C II H30 2

167.0133

165.0579

166.0532

C II H21 N

167.1675

C I3 H9
166

165.0705

C II H6N 2
C I2 H22
C I2 H6O

166.1722

167.0371

166.0419

CIIHsNO
C II H7N2

CSHI4N204
C6H2N20 4

166.0954

166.0657

C I2 H23

167.1801

166.0783

166.0253

C I2 HP
C I2 H9N

167.0497

C6H4NP3
C6H6N40 2
C7H4N04

C I2 HSN
CI3 H IO
167

166.0491
166.0140

C6 H3N20 4
C6 HSNP3

167.0093
167.0331

CI3 HII
168

167.0861

166.0379

167.0570

C6H4NP4
C6H6NP3
C6HSN 402

168.0171

C7H6N20 3
C7HsNP2
C7H ION4O

166.0014

CSH604
CsHsN0 3

166.0266

C6H7N40 2
C7HsN0 4
C7H7NP3
C7H9N 30 2

166.0504

C7H N4O

CsH. oNP2
CSH. 2NP
CSH.4N4
C9 H I00 3

166.0743
166.1220

C9 H. 2N0 2

166.0617
166.0856

167.0218
167.0451
167.0695

167.0484

167.0610

167.0736

168.0410
168.0648
168.0297

167.0934

C7H6N04
C7HsN 20 3

CSHP4
CSH9N0 3

167.0344

C7H. oN30 2

168.0774

167.0583

C7 H. 2N4O

168.1012

CsH N20 2
CsH I3 N P

167.0821
167.1060

CgHg04
CsH. oN0 3

168.0422

166.0630
166.0868

CSHISN4

167.1298

CSHI2N202

168.0899

166.0981

168.0535

168.0661

-,r

182

Spectroscopic Data Chemistry


FM

168.1138

CSH'4NP
CSH'6N4

168.1377

CsNp

168.0073

C9 H,z03
C9 H,4 N OZ

168.0786

C9 H'6 N ZO
C9N zO z
C9 H,sN 3
C9 HzN 3O
C9H4N4
C IO H'60Z
C lO O3

168.1025
168.1264
167.9960
168.1502
168.0198
168.0437
168.1151
167.9847

ClOH1SNO
CIOHzNO z

168.1389

CIOHzoN z
C lO H4N ZO
ClO H6N3

168.1628

168.0085
168.0324
168.0563

FM

C7H9N Z03
C7H ll N 3O Z

169.0614

C'4 H

169.0852

170

169.1 091

C6H6NP4
C6HsN30 3

170.0328

C6H lO N 4O Z
C7HgN04

170.0805

C7H,oN z0 3
C7H'2 N 30Z
C7H'4N40
CSH IOO4
CsH,zN0 3
CSH'4NZOZ

170.0692

CSH'6N30
CsNPz
C8HlSN4
C8HzN 4O

170.1295

C7H 13N P
CSH904
C8H"N0 3
CgH 13 N Z0 2

169.0978

CsH,sNP

169.1216

CSH'7N4
CSHN40
C9H l3 0 3

169.1455

C 9H,sNO z
C9 H'7 N ZO

169.1103

169.0501
169.0739

169.0151
169.0865
169.1342

C9 HNPz
C9H'9N3
C9 H3NP
C9HSN4

169.0038

C IO H'70Z
C lO H0 3

169.1229

169.1580
169.0277
169.0515

CllHzoO
C ll H40 Z

168.1515

C"HzzN
C ll H6NO

C IOH,9NO
C lO H3NO z

169.1467

168.1753
168.0449

C IO Hz,N2

169.1706

CllHgN Z

168.0688

C,zH Z4
C,zHgO

CIOHSNP
ClOH7N3

169.0402

168.1879
168.0575

CllHzp

C,zHION
C'3 H IZ

168.0814

C'4

168.0000

CllHsOz
C ll Hz3 N
C ll H7NO

169.0767

C6HSNP4
C6H7N 30 3
C6H9N40 2

169.0249

C ll H9N2
C'2 H2S

169.0726

C,zH 9O
C'2 H ll N

169.0653

C7H7N0 4

169.0375

C'3 H 13

168.0211

168.0939

169

169.0488

FM

168.9925
169.0164

169.0078

170.0566
170.0453
170.0930
170.1169
170.0579
170.0817
170.1056
169.9991
170.1533
170.0229

C9 H'403
C9 H,6 N OZ
C9N0 3

170.0943

C9H 1SN2O
C9 H2NPz

170.1420

170. Il82
169.9878
170.0Il6
170.1659
170.0355

169.1593

C9H20N3
C9H4NP
C9 H6N4

169.0289

CIOHlgO Z

170.1307

169.1832

CIOHzO,
CIOHzoNO
C,oH4N0 2

170.0003

170.1784

169.0892

ClOH2ZN2
ClO H6 N2O
ClO H8N3

169.1018

C'I H220

170.1671

169.0641

169.0528
169.1957

170.0594

170.1546
170.0242
170.0480
170.0719

183

Mass Spectrometry
FM

FM

C II H60 2

170.0368

171.0672

FM

172.0147

C 11 H24N

170.1910

C9H7N4
C IO H I9 0 2

171.1385

CgH2NP2
CgH20N4

C11HgNO

170.0606

C IO H30 3

171.0082

C gH4Np

172.0386

CIIHION2
C I2 H26

170.0845

C IOH21 NO

171.1624

C9H I6 0 3

172.1100

170.2036

171.0320

C90 4

171.9796

C1zH1OO
C I2 H I2N
C13 H I4
C I3 N

170.0732

CIO HSN 02
CIO H23N 2

171.1863

C9H 1gN0 2

172.1338

171.0559

C9H2N0 3

172.0034

170.1096

CIO H7NP
CIO H9N 3

171.0798

172.1577

170.0031

C II H23 0

171.1750

C9H20NP
C9H4N 20 2

C I4 H2

170.0157

C II H70 2

171.0446

172.1815

C II H25 N

171.1988

171.0406

C II H9NO

171.0684

C9H22N3
C9H6N P
C9HgN4

170.0970

171

C6H7NP4
C6H9N 30 3

172.1690

172.0273
172.0511
172.0750

171.0644

C II H II N 2

171.0923

C6H II N 40 2
C7H9N0 4

171.0883

C I2 H II 0

171.0810

171.0532

C I2 HI3N

171.1049

C7HIIN203

171.0770

C 13 H I5

171.1174

C7HI3N30Z
C7H I5N 4O
CgH II 0 4

171.1009

CI3 HN

171.0109

171.1247

C I4 H3

171.0235

CIOH24N2
C IO HgN 2O

172.1941

171.0657

172

171.0896

172.0484

CgHISN202
CgH I7N3O

171.1134

C6HgN Z0 4
C6H ION30 3

CIO H ION3
C II H240

172.0876

CgHI3 N0 3

172.0723

C II Hg02

172.0524

C6HI2N402
C7H 1ON04

172.0961

172.0763

172.0610

CIINIONO
C II H I2N2

172.1001

172.0848

C I2 H I2 O

172.0888

C I2 HI4N

172.1127

C I2N 2
C 13 H I6

172.0062

172.0022
172.0735

C I3 0

171.9949
172.0187

171.1373

CloH2002
C 1oH40 3
C IOH22NO
C 1oH6N0 2

CgHNP2
CgHI9N4

171.0069
171.1611

C7HI2Nz03

CgH3Np
C9H I5 0 3

171.0308
171.1021

C7HI4N302
C7HI6NP

C9H I7N0 2

171.1260

C9HN0 3

170.9956

C7NP2
CgH I2 0 4

C9H I9N zO
C9H3N 20 2

171.1498

CgH I4N0 3

172.0974

C13 H2N
C I4 H4

C9HzIN3
C9 H5N,0

171.1737

CgHl6NZOz
CgN10 3

172.1213
171.9909

173

171.0433

CgH\gNp

172.1451

C6H9NZ04

171.0195

"
172.1087
172.1325

172.1464
172.0160
172.1702
172.0399
172.0637
172.1828

172.1253

172.0313
173.0563

184

Spectroscopic Data Chemistry


FM

FM

C6HIIN303

173.0801

C 11 H13 N2

173.1080

C6Hl3N402
C7H ll N04

173.1040

173.0967

173.0688

C 12H'30
C'2 HlSN

C7Hl3N203

173.0927

C l2 HN 2

C7HlSN302
C7Hl7NP

173.1165

C7HNP2
CgH l3 0 4

FM
174.0429

173.1205

C9H6N20 2
C9HgNp
C9H lON4

173.0140

C lO H22 0 2

174.1620

C l3 H l7

173.1331

C 1oH60 3

174.0317

173.1404

C13 HO

173.0027
173.0266

173.0814

C l3 H3N
C l4HS

ClOHgN02
ClOH lON 2O

174.0555

173.0100

174.1032

CgH,sN0 3

173.1052

174

C IOH'2N3
C ll H lOO2

CgHl7NP2
CgHNP3
CgH'9NP

173.1291

C6H lON20 4
C6Hl2N303

174.0641

C6Hl4N402
C7Hl2N04

174.1118

C ll H,2NO
C ll H 14N2
C ll N3

174.0919

172.9987

174.0766

C7HI4N203

174.1005

C 12H'40
C l2 H l6N

174.1045

173.1768
173.0464

C7Hl6N302
C7N30 3
C7H 1gN4O
C7H2N40 2

174.1244

C'2NO
C l2 H2N2
C I3 H,g

173.9980

CgH3NP2
CgH21 N4
CgHSN40
C9H l7 0 3

173.1529
173.0226

173.1178

C9H04
C9H l9N02
C9H3N03

173.1416

C9H21NP

173.1655

C9 HSNP2

172.9874

173.0391

174.0879

173.9940
174.1482
174.0178

174.0668
174.0907

174.0794
174.0681
174.1158
174.0093
174.1284
174.0218
174.1409
174.0106

174.0892
174.1131

C l4 H6

173.0351

C SH l404
CgH I6N..3
CgN04

C l3 HP
C13 H4N

173.9827

175

C9H23N 3

173.1894

CgHlgN202

174.1369

175.0719

C9 H7NP

173.0590

C9H9N4
CloH2102
C 1oHs0 3
C lO H23 NO

173.0829

175.1196

174.0304

C6HlSN402
C7H l3 N04

175.0845

174.1846

C7HlSN203

175.1083

173.1781

CgH2NP3
CSH20Np
CgH4NP2
CgH22N4
CgH6N4O

C6H ll N20 4
C6Hl3N303

174.0542

175.1322

C lO H7N0 2

173.0477

C7Hl7N302
C7HN 30 3

C 1o H9NP
ClOHllN3
C ll H90 2

173.0715

175.1560

CllHllNO

173.0841

C7H l9NP
C7H3N40 2
CgH 1S 0 4
CgH l7N0 3

173.0113

173.1542
173.0238

173.0954
173.0603

C9H 1g0 3
C9HP4
C9H20N0 2
C9H4N0 3
C9H22N2O

174.0065
174.1608

174.1256
173.9953
174.1495
174.0191
174.1733

174.0344
174.0470

175.0958

175.0018
175.0257
175.0970
175.1209

185

Mass Spectrometry
FM

FM

FM

C6HI6N402
C7HI4N0 4

176.1275

C I2 0 2

175.9898

176.0923

C I2 H 1g N

176.1440

175.0144

C7HI6N203

176.1162

C I2 H2NO

176.0136

CgH21 Np

175.1686

C7NP4

175.9858

C I2 H4N 2

176.0375

CgH5NP2
CgH7N40

175.0382

176.1400

C 13 H20

176.1566

175.0621

C7HIgN302
C7H2N30 3

176.0096

C I3 H4O

176.0262

C9H I9 0 3

175.1334

C7H20N 4O

176.1639

C I3 H6N

176.0501

C9HP4
C9H21 N0 2

175.0031

C7H4N40 2

176.0335

C I4 Hg

176.0626

175.1573

CgH I60 4

176.1049

177

C9H5N0 3

175.0269

CgH 1gN0 3

176.1287

C6HI3N204

177.0876

C9H7NP2
C9H9N P

175.0508

CgH2N0 4

175.9983

C6HI5N303

177.1114

175.0746

176.1526

175.0985

176.0222

C6HI7N402
C7H I5N04

177.1353

C9HIIN4
C IO H70 3

175.0395

CSH20N202
CgH2NP3
CSH6N302

176.0460

C7HI7N203

177.1240

C 1o H9N0 2

175.0634

CgHgN40

176.0699

C7HNP4

176.9936

CioHIIN20
CIO H 13 N3

175.0872

C9H200 3

176.1413

177.1478

175.1111

176.0109

C II HII 0 2

175.0759

C9HP4
C9H6N0 3

C7HI9N302
C7H3N30 3

176.0348

C7H5N40 2

177.0413

C II H I3 NO

175.0998

C9HgN 20 2

176.0586

CgH I7 0 4

177.1127

C II HI5N 2

175.1236

C9H ION30

176.0825

177.1365

C 11 HN 3

175.0171

176.1063

C I2 H I5 O

175.1123

C9HI2N4
C IO Hs0 3

CSH I9N0 3
CSH3N 04

C I2 H I7N

175.1362

C IO H ION0 2

176.0712

C I2 HNO

175.0058
175.0297

C IO H I2 N2O
C to Hl4N3

176.0950

C I2 H3N2
C I3 H I9

175.1488

C 1oN4

C I3 H3O

175.0184

C II H I2 0 2

C13 H5N
C I4 H7
176

175.0422
175.0548

CgHN04

174.9905

CgHI9 NP2
CgH3N20 3

175.1447

C6HI2N204
C6HI4 N)03

176.0473

CSH5N 20 3
CSH 7N 302

177.1001

177.0175

177.0062
177.0300
177.0539
177.0187

176.0124

CSH9N 4O
C9HP4
C9H7N0 3

176.0837

C9H 9NPz

177.0664

C 11 N I4 NO

176.1076

C9H 11 N3O

177.0903

C9HI3 N4
C 1o H90 3

177.1142

176.0797

CIIHl6N2
C 11 N2O
C II HzN3

176.1315

176.1036

C I2 H I6 O

176.1202

176.1189

176.0011
176.0249

CioHIIN02
C to HI3 N 2O

177.0777
177.0426

177.0552
177.0790
177.1029

186

Spectroscopic Data Chemistry

FM
ClOH1SN J
C 1O HN 4

177.1267

FM
178.0743

177.0202

C9HION202
C9 H I2N JO

178.0981

C 11 H I3 0 2
C 11 H I5 NO

177.0916

C9HI4N4

178.1220

CIIHI7N2

177.1393

CIOHIOO J
C lO HI2N0 2

178.0630

C11HNP
C 11 H3N J

177.0089

C lO HI4N 2O

178.1107

177.0328

C I2 H I7 O

177.1280

CloHI6N3
CIONJO

178.0042

C I2 H0 2
C I2 H I9N

176.9976

C I2 H3NO
C I2 HSN2
C13 H21

177.1154

178.0868
1781346

FM
CgH7N20J
CgHgNP2
CgH 11 N 4O

179.0457
179.0695
179.0934

C9HP4
C9H9N0 3

179.0344

C9HIIN202
C9HI3 N P

179.0821
179.1298
179.0947

179.0583
179.1060

178.0280

177.1519

ClOH2N4
C II H I4 0 2

178.0994

C9HISN4
C toH II 0 3
C to H 13N0 2

177.0215

C 11 H I6NO

178.1233

C IO H1SN 2O

179.1185

177.0453

C II N0 2

177.9929

179.1424

177.1644

179.0120

179.0708

C II H 1gN 2

178.1471

CI3 HsO
C I3 H7N

177.0340

C II H2N 2O

178.0167

CIO HI7N 3
CIOHNP
C IOHJN 4

177.0579

C 11 H4N 3

178.0406

C II H 1S0 2

179.1072

C I4 H9

177.0705

C I2 H 1g O

178.1358

C II H I7NO

179.1311

C II HN0 2
C II H I9N 2
C II H3N 2O

179.0007

178

179.0359

CI2 H20 2

178.0054

C6HI4N204
C6HI6N303
C6HIgN402
C7HI6N0 4

178.0954
178.1193

CI21120N
C I2 H4NO

178.1587

178.1431

C I2 H6N2
C I3 H22

178.0532
178.1722

C II HSN3
C I2 H I9 O

C7HIgN203
C7H2N 20 4

178.1318

178.0419

C I2 H30 2

179.0133

178.0014

C\3H6O
C I3 H gN

178.0657

C I2 H21 N

179.1675

C7H4N30 3

178.0253

C I4 H lO

178.0783

C I2 HSNO

179.0371

C7H6N 40 2

178.0491

179

C I2 H7N 2

179.0610

CgH 1g04
CgH4N04

178.1205

C6HISN204

179.1032

C 13 H23

179.1801

178.0379

C I3 HP
C I3 H9N

179.0497

CgH6N Z0 3

C6HI7N303
C7HI7N04

179.1271

179.0736

CgHgN30 2

178.0617

179.0861

178.0856

179.0093
179.0331

C I4 H II

CgHIONp
C9H60 4

C 7H3NZ04
C7HsN 30 3

178.0266

C7H7N 40 2

179.0570

C9HgN0 3

178.0504

CgHSN0 4

179.0218

C6HI6N204
C7H4N 20 4

178.1080

178.0140

178.0293

179.1158

179.1549
179.0246
179.0484
179.1436

180
180.1111
180.0171

187

Mass Spectrometry
FM

FM

18l.l593

180.0814

C 12 H2P
C l2 Hs0 2

180.0939

C I2 H23N

18l.l832

180.0000

C I2 H7NO

181.0528
181.0767

C7HsN 20 4

181.0249

C I2 H9N l
C I3 H1S

C 7H7NP3
C7H9N4Oz

181.0488

C7H6NP3

180.0410

C I3 HgO

180.0575

C7HgNP2
CgH6N 04

180.0648

CgHgNP3
CgH ION 30 2

180.0535
180.0774

CI3 H ION
C I4 H I2
CIS
181

CgH I1N4O

180.1012

C9Hg04
C9H ION0 3

180.0422

180.0297

180.0661

FM

181.0289

181.1957
181.0653

181.0726

C I3 HP
C I3 H II N

181.0892

C9HI1N1OZ

180.0899

C I4 H I3

181.1018

180.1138

CgH7N 04
CgH9N Z0 3

181.0375

C9H I4N 3O

181.0614

181.0078

C9HI6N 4
C9N 4O

180.1377

C SH II N 30 Z

181.0852

ClsH
182

180.0073

CSH I3 N 4O

181.1091

182.0328

C IO H IZ 0 3

180.0786

C9H90 4

181.0501

182.0566

C IO H I4NO z

180.1025

C9H II N0 3

181.0739

C7H6N Z04
C7HsNP3
C7H ION 4OZ

C IO HI6N zO

180.1264

181.0978

CgHgN04

182.0453

CION1O Z

179.9960

C9HI3NzOz
C9H IS N3O

181.1216

CgH IONZ0 3

182.0692

CIOH IgN 3

180.1502

181.0151

CIO H4N4
C II H I6 0 Z

180.0437

C IO H I3 0 3

181.0863

180.1151

C II 0 3

179.9847
180.1389

CIOHlsNO z
C IO H I7N zO
C IOHN2OZ
CloHI9N3
CIO H3N30

CgHIZN30Z
CgH I4 N4O
C9H IOO4
C9H I1N0 3

182.0930

180.0198

C9HI7N4
C9HN4O

18l.l455

C IO HzN 3O

CllHlsNO
C II H2NO z

180.0085

C II HzoN 2

180.1628

C II H4NP
C II H6N3

180.0324

181.1103
181.1342

182.0805

182.1169
182.0579
182.0817
182.1056

181.0038

C9HI4NzOz
C9H I6N3O

182.1295

181.1580

C9N 3O Z

181.9991

181.0277

182.1533
182.0229

181.0515

180.0563

CIO HSN 4
C II H I7 0 Z

C9HISN4
C9 HzN4O

181.1229

CloHI403

182.0943

ClzHzoO
C lz H40 Z

180.1515

C II H0 3

180.9925

182.1182

180.0211

C II H I9NO

181.1467

CIOHI6NOz
C loN0 3

C IZ HZ2N

180.1753

C II H3NOz

181.0164

CJONlgNZO

182.1420

C IZ H6NO

180.0449

181.1706
181.0402

182.0116

180.0688

CIIH21Nz
CllHsNzO
C II H7N 3

CIOH2NzOz

CI1HgN Z
C I3 Hz4

C JO HzoN3
C JO H4N3O

182.1659

180.1879

181.0641

181.9878

182.0355

Spectroscopic Data Chemistry

188
FM

C 1oH6N 4
CIIHIg02
C 11 H2OJ

182.0594

C 11 H20NO

182.1546

C 11 H4N0 2
C 11 H22N 2

182.1784

182.1307
182.0003
182.0242

FM

FM

C9HI9N4
C9HJNp

CIOH1SOJ
C lO H I7N0 2

CgH ION04

184.0610

183.0308

CgHI2N20J

184.0848

183.1021

CgHI4NJ02
CgH l6Np

184.1087

183.1611

183.1260
182.9956

184.1325
184.0022

182.0480

CIOHNO J
C lO H l9N 2O
C lO HJN 20 2

182.0719

C IOH21 N J

183.1737

182.1671

CIOHSNJ O

183.0433
183.0672

182.1910

CIOH7N4
C ll H l90 2

182.0606

C 11 H30 3

183.0082

C l2 H ION 2

182.0845

C 11 H21 NO

183.1624

C9H20N4
C9H4N4O

C 13 H26

182.2036

C ll HsN02

183.0320

C IO H l6 0 3

184.1 100

183.1863

C IOO4

183.9796

183.0559

184.1338
184.0034

C 11 H6N P
CllHgN J
C l2 H22 O
C I2 H60 2

182.0368

C l2 Hz4N
C l2 HgNO

C 13 H 1OO

182.0732

C13 H I2N

182.0970

C l4 H I4

182.1096

C I4N
C 1s H2

183.1498
183.0195

183.1385

CgNP2
C9 H l20 4
C9HI4NO J
C9Hl6NP2
C9N 2OJ
C9H,gNP
C9H2N30 2

184.073~

184.0974
184.1213
184.9909
184.1451
184.0147
184.1690
184.0386

183.0798

CIOHIgN02
C IOH2N0 3

182.0031

CIIH23N2
C ll H7N2O
C lI H9N 3
C 12 H23 O

183.1750

CloH20N20

184.1577

182.0157

C I2 H70 2

183.0446

CloH4N202

184.0273

C l2 H2SN

183.1988

184.1815

183

C7H7N 20 4

183.0406

C I2 H9NO

183.0684

CloH22N3
C 1oH6N3O

C 7H9NP3 .

183.0644

C I2 H ll N 2

183.0923

CIOHgN 4

184.0750

C7H ll N 40 2

183.0883

C I3 H27

183.2114

C Il H200 2

184.1464

CgH9N 04

183.0532

183.0810

C Il H40 3

184.0160

183.1049

C ll H22 NO

184.1702

184.0511

CgHIIN203

183.0770

C 13 H 1P
C13 H I3 N

CgHl3NJ02
C gH 1SN 4O

183.1009

C l4 H 1S

183.1174

C 11 H6N0 2

184.0399

183.1247

C l4 HN

183.0109

C ll H24N 2

184.1941

C9 H l1 0 4

183.0657

C 1s H3

183.0235

C ll HgN 20

184.0637

C9H1J NO J

183.0896

184

C 11 H ION 3

184.0876

C9HISNz02
C9H I7N JO

183.1134

C7HgN 20 4

184.0484

C I2 H24 O

184.1828

183.1373

C7 H ION 3OJ

184.0723

C l2 Hg0 2

184.0524

C9 HNP2

183.0069

C7Hl2N40Z

184.0961

C1'2 H26N

184.2067

,.

189

Mass Spectrometry

FM

FM

FM
CJOH0 4
C JO H23 N3

184.9874

C RH2N40 2

186.0178

185.1894

186.0892

CJOH 7Np
C JO H9N 4

185.0590

C)1 J4 04
C9 H J6N0 3

185.0829

C9 N0 4

185.9827

185.1542
185.0238

C9 H JgNP2
C9H2N2OJ

186.1369

184.0062

CIIHzpz
C JJ H50 3

184.1253

C JJ H23 NO

185.1781

C9 HzoNp

186.1608
186.0304

C J2 HJONO

184.0763

CJ2HJ2NZ
C J3 H2g

184.1001

C J3 H JZ O

184.0888

CJ3H J4N
C J3 N Z

184.1127

C J4 H J6

184.2192

186.1131

186.0065

C J4 0

183.9949

C JJ H7NO Z

185.0477

C9H4N30 2

C J4 HZN

184.0187

185.2019

C9 H zz N 4

186.1846

C J5 H4

184.0313

CJJHZ5NZ
C JJ H9N ZO

185.0715

186.0542

185.0563

C JJ HIJN 3
C JZ HZ5 0

185.0954

C 7H 9N Z04

185.1906

C9 H6NP
CJOHJgO J
C JO HZ04

185.9953

C7HllN303
C7H J3 N4 OZ

185.0801

C JZ H90 Z

185.0603

C JO H1ON4

186.0907

185.1040

C 1z H z7N

185.2145

186.1495

CgHIJN04

185.0688

CJZHIJNO

185.0841

CJOHzoNO z
C JO H4N0 3

CgHJ3NZ03

185.0927

CJOH2ZNZO

186.1733

CgHl5N302
CS H J7N40

185.1165

185.0967

CJOH6NZ02

186.0429

185.1404

CJZHJ3NZ
CJ3H J3 O
Ct3 HI5N

185.1080
185.1205

186.1972

CgHNP2
C9H2J N4

185.0100

C l3 HN Z

185.0140

C JOH24NJ
C JO HgN3O

185.1768

C l4 H l7

185.1331

185.1529

C J4 HO

185.0027

185.0464

CJJH2Z0Z
C JJ H60 3
C JJ HZ4 NO

186.1620

185.0391

CJJHgNO Z

186.0555

CJ1HZ6N2

186.2098

185

186.1256

186.0191

186.0668
186.0317

C9 H J9N30
C9 H5N4O
C9H3N 30 2

185.0226

C l4 H3N
C l5 H5

C9 H I3 0 4

185.0814

186

C9H l5 N0 3
C9 H l7NPz

185.1052

C7HJON z0 4

186.0641

CJJHJON20

186.0794

185.1291

C7Hl2N303

186.0879

186.1032

C9 HNP3

184.9987

186.1118

186.1985

CJOHJ9NOZ
C JO H3N0 3

185.1416

C7Hl4N402
CgH JZ N0 4

CJJHJZN3
C JZ H260

186.0766

C J2 H JO O2

186.0681

185.0113

CgHJ4N203

186.1005

CJZHJZNO.

186.0919

CJOHZJNZO

185.1655
185.0351

185.9940

CJ2HJ4NZ
C JZ N 3

186.1158

CJOH5N20Z

186.0093

CJUHJ703

185.1178

CgHl6N30Z
CgNJO J
CgH Jg N40

186.1244
186.1482

C 13 H J4 O

186.1045

185.0266

186.1859

190

Spectroscopic Data Chemistry

FM
CI3 H I6N
C1JNO
C13 H2N2

186.0218

C I4 H 1g

186.1409

C I4 H2O

186.0106

C I4 H4N

186.0344

C l5 H6

186.0470

186.1284

FM

FM
187.2050

C9H I6 0 4

188.1049

187.0746

C9 H1gN0 3

188.1287

187.0985

C9 H2N0 4

187.9983

187.0872

188.1526

187.1111

C9H20NP2
C9H4N 20 3

CIIH2302
C 11 H70 3

187.1699

C9H22N 3O

188.1764

187.0395

C9 H6N 30 2

188.0460

C 11 H25NO

187.1937

C7HIIN204
C7H 13 N3OJ

187.0719

C 11 H9N0 2

187.0634

C9 H24N4
C9HgN 4O

188.2003

187.0958

C7HI5N40Z
CgH 1JN0 4
CgHI5N203

187.1196
187.0845
187.1083

CI2HI102
C I2 H 13NO
Cl2Hl5N2
C 1z HN 3

CgH I7NP2

187.1322

CgHNP3
CgH I9 N4O

187.0018
187.1560

CgH3N40 2
C9 H I5 0 4

185.9980

187

CIO H25 N3
C 1O H9N P
CIO H 11 N 4
CIIHIIN20
CIJH I3 N3

187.0759
187.0998

C1OH200J
CJOH 40 4

188.0222

188.0669
188.1413
188.0109
188.1651

187.0171

CloH22N02
C JO H6NO J

C I3 H I5 O

187.1123

CIOH24NzO

188.1890

C 1J H 17N

187.1362

CIOHgN202

188.0586

187.0058

C1oHJONJO

188.0825

187.0257
187.0970

CJ1HNO
C13 H3N 2

187.0297

CloHI2N4

188.1063

C I4 H I9

187.1488

188.1777

C9H I7N0 3

187.1209

C l4 H3O

187.0184

CIIHz402
CIJHg0 3

C9HN0 4

186.9905

CIJHJON0 2

188.0712

C9H I9NPl
C9H3N Z03

C I4 H5N
CI5 H7

187.0422

187.1447

187.0548

C 1I H I2NP

188.0950

187.0144

188

188.1189

C9H21 N3O

187.1686

C7HllN104

188.0797

CIIHI4N3
C 11 N 4

C9H5N 30 2

187.0382

C7HI4N303

188.1036

C9H23 N4
COH7Np

187.1925

C7HI6N402
CgH I4N0 4

188.1275

C IO H I9 0 3

187.1334

CJOH 30 4

187.0031

CgHI6N203
CgN10 4

CloH21N02
C 1o H5N0 3

187.1573

187.1236

188.0348

188.0473

188.0124

ClzHI20Z
C I2 H I4NO

188.0837
188.1315

188.1162

CI2HI6N2
C 11 N2O

187.9858

C I2 H2N 3

188.0249

C I3 H I6 O

188.1202

187.0269

CgHIgN30Z
CgH2N3 0 3

188.1400
188.0096

C 13 0 2

187.9898

CloH23N20

187.1811

C gH20N2O

188.1639

C I3 H 1g N

188.1440

CJOH 7NP2

187.0508

CgH4N402

188.0335

C I3 H2NO

188.0136

187.0621

188.0923

188.1076
188.0011

191

Mass Spectrometry

C13 H4N2
C 14H20

188.0375

CIIHIINOz

189.0790

188.1566

CIIH13N20

189.1029

C 14H4O

188.0262

189.1267

C 14H6N

188.0501

CIIHlSN3
C ll HN 4

C1SHg

188.0626

C12H1302
C 12H 1S NO

189.0916
189.1393
189.0089

189

189.0202
189.1154

C7H!3N 20 4

189.0876

C7HlSN303

189.1114

C7H17N402
CgH 1S N0 4

189.1353

C12H17N2
C 12 HNP
C 12H3N 3

189.1001

C 13 H 17O

189.1280

CgH17N203

189.1240

C 13 H02

188.9976

CgHNP4

188.9936

189.1519

CgH19N302

189.1478

C!3 H 19N
C 13 H3NO

CgH3NP3
CgH21 N4O

189.0175

C 13 HSN2

189.0453

189.1717

C 14H21

189.1644

CgHSN 40 2

189.0413

C 14 HsO

189.0340

C9H 170 4

189.1127

C 14 H7N

189.0579

C9H 19N0 3

189.1365

C 1s H9

189.0705

C9H3N0 4
C9H21N202
C9 HSNP3
C9H23 N3O

189.0062

190.

189.1604

C7H14N204

190.0954

189.0300
189.1842

C7H16N303
C7HlgN402
CgH 16N0 4

190.1193
190.1431

189.0539

FM

FM

FM

189.0328

189.0215

190.1080

C9 Hz2 NP2
C9 H6N 20 3

190.1682

C9 HgN30 2
C9H 1ON 4O
CloH2203
C 1o H60 4
C 1OHgN0 3

190.0617
190.0856

CloHION202
ClOH12NP
CloH14N4
C ll H 1OO3
CIIHI2N02
C ll H 14NP
C ll H 16N3
C11NP
C 11 H2N4
C12H1402
C 12HI6NO
C 12N0 2
C12HlgN2
C 12 H2NP
C 12 H4N3
C 13 H 1gO
C 13 H20 2

C9H7NP2
C9H9NP

189.0777

CgH 1gNP3

190.1318

C lO H21 0 3

189.1491

190.0014

C lO Hs04
C lO H23N0 2

189.0187
189.1730

CgH2NP4
CgH20N302
CgH4N30 3

C 1oH7N0 3

189.0426

CgH22N4O

190.1795

CloH9N202
C io H II N3O

189.0664

CgH6N 40 2

190.0491

C13 H20N
C 13 H4NO
C13 H6N 2
C I4 H22
C I4 H6 O
C I4 HgN

189.0903

C9H 1g0 4

190.1205

C1sH 1O

CloHI3N4
C 11 H90 3

189.1142

C9H20N3
C9H4N04

190.1444

191

190.0140

C7HISNz04

189.0552

190.1557
190.0253

190.0379

190.1569
190.0266
190.0504
190.0743
190.0981
190.1220
190.0630
190.0868
190.1107
190.1346
190.0042
190.0280
190.0994
190.1233
189.9929
190.1471
190.0167
190.0406
190.1358
190.0054
190.1597
190.0293
190.0532
190.1722
190.0419
190.0657
190.0783
191.1032

Spectroscopic Data Chemistry

192

FM

FM

FM

C7Hl7N303

191.1271

C l3 H3 0 2

191.0133

C ll H lgN3

192.1502

C7Hl9N40Z
CgH l7N0 4

19L1509

191.1675

C ll H2 N3O

192.0198

191.0371

C ll H4N 4

192.0437

CgHl9NZ03

191.l396

C13 HZl N
C l3 HSNO
C l3 H7Nz

191.0610

192.1151

CgH3NP4

191.0093

C l4 Hz3

191.1801

ClzHl60Z
C l2 0 3

191.9847

CgHZlN302

191.1635

C l4 H7O

191.0497

ClZHlgNO

192.1389

CgHSNP3
CgH 7N40Z

191.0331

C l4 H9N

191.0736

ClzHzNO z

192.0085

191.0570

191.0861

191.1284
191.1522

192.1111

ClzHzoNz
C 1ZH4N zO
C lz H6N 3

192.1628

C9H I9 0 4
C9H2l N0 3

ClsH 11
192
C7H l6N Z04

C9HSN04
C9H7NP3
C9H9N 30Z

191.0218

C7HlgN303

192.1349

C 13 HZOO

192.1515

191.0457

C7H20NPz
CgH 1gN0 4

192.1588

C 13 H4OZ

192.0211

192.1236

C l3 Hzz N
C l3 H6NO

192.1753

192.1475
192.0171

C 13 HgN Z

192.0688

191.1158

191.0695

192.0324
192.0563

192.0449

C9 H ll N 4O

191.0934

C lO H70 4

191.0344

CgHZONZ03
CgH4N Z04

C lO H9N0 3

191.0583

CgH6N30 3

192.0410

C I4 Hz4

192.1879

C lO H ll N 2OZ 191.0821

CgHgN40 Z

192.0648

C l4 HgO

192.0575

C lO H l3 N3O

191.1060

C9Hzo 0 4

192.1362

C l4 H lON

192.0814

CIOHlSN4
C II H lI 0 3

19l.l298

C9 H6N04

192.0297

192.0939

191.0708

192.0535

C lI H I3NO z

191.0947

C9 HgNP3
C9 H lON3OZ

ClsH 1Z
C I6

192.0774

193

CllHlSN20

191.1185

C9H lZN4O

192.1012

C7Hl7N204

193.1189

ClIHI7N3
C ll HN 30

19l.l424

C lO Hg04

192.0422

CioHlON03

192.0661

C 11 H3N4

191.0359

ClOHl2Nz02

192.0899

C7HI9N303
CgH l9N04
CgH SN Z0 4

193.1427

191.0120

ClzHISOZ
C I2 H l7NO

19I.1072

CloHl4N30

192.1138

193.0488

191.1311

192.1377

C1zHNO z

191.0007

CloHl6N4
C lON 4O

CgH7NP3
CgH9N40 2

192.0073

C9H 7N0 4

193.0375

Cl2HI9Nz
C 1Z H3N P

191.1549

192.0786

191.0484

192.1264

C9H9N 20 3
C9HIIN302
C9 H 13 N40

193.0614

C 12 HsN3
C 13 H I9 O

CllHl203
CllHl4N02
C ll H l6N zO

191.1436

C ll Nz0 2

191.9960

C9 H7N3O

193.0590

191.0246

192.1025

192.0000

193.1315
193.0249
193.0726

193.0852
193.1091

193

Mass Spectrometry

C 1oH90 4

193.0501

CioHIIN03

193.0739

CIOHI3N202
C IO H 1SN 3O

193.0978
193.1216

FM

FM

FM

194.0606

CgH6NP4
CgHgNP3

194.0328
194.0566

CI3 HgNO
C13 H ION 2

CgHION402
C9HgN04

194.0805

C I4 H26

194.1036

194.0453

C I4 H 1OO

194.0732

C I4 H I2N

194.0970

194.0845

CloHI7N4

193.1455

C9H 1ONP3

194.0692

CIOHNP
C II H I3 0 3

193.0151

C9HI2N302

194.0930

C 1s H I4

194.1096

193.0865

194.1169

193.1103

194.0579

ClsN
C I6 H2

194.0031

CIIHISN02

C9HI4NP
C IOH 1004

CIIHI7NzO

193.1342

C IO H 1ZN0 3

194.0817

195

CIIHNPz

193.0038

194.1056

193.1580

CgH7NP4
CgH9NP3

195.0406

CIIHI9N3
C II H3N P

CIOHI4NzOz
C IO H I6N3O

193.0277

C ION3OZ

193.9991

C II HSN4

193.0515

CIO H1gN 4

194.1533

C9HIIN402
C9H9N04

195.0883

ClzHI70Z
C 1z H0 3

193.1229

C IO HzN4O

194.0229

C9H II N z0 3

195.0770

192.9925

C II H I4 0 3

194.0943

193.1467

C II H I6NO z

194.1182

C 1Z H3NOz

193.0164

C II N0 3

193.9878

ClzHzlNz
C I2 HsNp
C I2 H7N 3

193.1706

CIIH1gNZO

194.1420

C9HI3N30Z
C9H 1SN4O
C IO H 1104
C IOH 13N0 3

195.1009

C 1Z H I9NO

193.0402

194.1659

CIOHISN20Z
C IOH I7N3O

195.1134

193.0641

CIIHzNzO z
C II HzoN3

194.0116

195.1373

C I3 H21 O

193.1593

C II H4N3O

194.0355

C IO HN 30 2

195.0069

C I3 Hs02
C I3 H23 N

193.0289

194.0594

193.0528

194.0003

CIO HI9N4
CIO H3N4 O
C II H 1S 0 3

195.1611

C 13 H7NO

C II H6N 4
CIZHlgOZ
C 1z Hz0 3

195.1021

C I3 H9N 2
C I4 Hzs

193.0767

C 1Z H20NO

194.1546

C II H I7NO z

195.1260

193.1957

C 1Z H4NOz

194.0242

C II HN0 3

194.9956

C I4 H9O

193.0653

194.1784

C II HI9N zO

195.1498

C I4 H 11 N

193.0892

ClzHz2N2
C I2 H6 N 2O
C 1ZHgN3
C 13 H2Z O

194.0480

CIIH3NzOz

195.0195

194.1671

CIIHzIN3
C 11 HsN 3 O

195.1737

C I3 H6OZ

194.0368

C IlH7N4

195.0672

C I3 H24N

194.1910

CI2HI902

195.1385

193.1832

C 1sH I3

193.1018

C I6 H

193.0078

194

C7H 1gNP4

194.1267

194.1295

194.1307

194.0719

194.0157

195.0644
195.0532

195.1247
195.0657
195.0896

195.0308

195.0433

Spectroscopic Data Chemistry

194

C,zH 30 3
C'2 H2I NO

195.0082

C,zH sN0 2
C'2 HZ3 N2

195.0320

C,zH 7N zO
C'2 H9N3

195.0559

C 13 H2P
C'3 H70Z

195.1750

195.1624
195.1863
195.0798
195.0446
195.1988

C'3 Hzs N
C13 H9NO
C'3 H II N2

195.0684
195.0923
195.2114

C'4 HZ7
C'4 H IIO
C'4 H '3N

195.0810

C,sH,s
C,sHN
C'6 H3

195.0109

195.1049
195.1174
195.0235

196

CgHgNZ0 4
CgH ION30 3

196.0484

CgH,zN 40 2
C9H ION04

196.0961

C9 H,zN z0

196.0848

196.0723
196.0610
196.1087

C9HI4N302
C9 H'6N40

196.1325

C9N 4OZ

196.0022

C IO H 1Z 0 4

196.0735

C IO H,4N03
C'OH'6N ZOZ

196.0974

C,oN Z0 3
C IO H,gN 3O

195.9909
196.1451

CIOHzNPz

196.1213

196.0147

FM

FM

FM

CIO HZON 4
C IO H4N4 O
C II H'603
C II 0 4
CIIH,sNO z
C II H1N0 3
CIlI-twNP
C II H4NZ02
C"H zz N 3
C II H6N3O
C II HgN4
C'2 H200Z
C'2 H403
C'ZH22NO
C,zH6NO z
C'2 HZ4 N2
C'2 HgN ZO
C,zH,oN 3
C'3 H240
C'3 HPZ
C13 H26N
C'3 H IONO
C 13 H I2Nz
C'4 H2g
C I4 H,zO
C'4 H I4 N
C'4N 2
C 1s H'6
C,p
C 1s H2N
C'6 H4

196.1690
196.0386
196.1100
195.9796
196.1338
196.0034
196.1577
196.0273
196.1815
196.0511
196.0750
196.1464
196.0160
196.1702
196.0399
196.1941
196.0637
196.0876
196.1828
196.0524
196.2067
196.0763
196.1001
196.2192
196.0888
196.1127
196.0062
196.1253
195.9949
196.0187
196.0313

197

CgH9NP4

197.0563

CgH'I N303
CgH 13 N40 2
CqH Il N0 4
C9H13 NZ0 3

197.080 I

C9H,sN 3OZ
C9H'7N40
C9HN 4OZ

197.1165
197.0100

C IO H 13 0 4

197.0814

C,oH 1SN0 3

197.1052

197.1040
197.0688
197.0927
197.1404

C'OH I7NzOz 197.1291


196.9987
C IO HNP3
C lO H l9 N3O 197.1529
C,oH 3N3OZ

197.0226

C,oH z,N 4
C,oH sN4 O

197.1768
197.0464

C II H'703
C II H0 4

197.1178
196.9874

C II H'9NOZ
C"H 3N03
C lI H2,N2O
ClI HSNz02

197.1416

C II H23 N3

197.1894

C II H7N3O
C II H9N4

197.0590

C,zH 2 Pz
C,zH 50 3

197.1542

C'ZH 23 NO
C,zH 7NO z
C'2 H2SN Z

197.1781

C,zH 9 N1 O
C'2 H II N,

197.0715

C 13 H2S O

197.1906

197.0113
197.1655
197.0351

197.0829
197.0238
197.0477
197.2019
197.0954

195

Mass Spectrometry

CgH13 NP3
CgH,sN 4OZ
C9H,3 N04

199.0958

C9H,sN z0 3
C9H'7N302

199.1083

CIIHgNp
C II H ION4

C9HNP3
C9H'9N40

199.0018

198.0668
198.0907

C9H3NP2

199.0257

C'2H2202
C,zH 60 3
C'2HZ4NO

198.1620

199.0970

C'2HgN02
C'2 HZ6N2
C'2 H ,oN 2O
C'2 H'2N3
C'3 H260

198.0555

C'OH'S04
C'OH'7N 03
C,oHN04
C IOH'9NPZ
C,oH3N20 3
C,oH2,N 3O
C IO HsN3OZ

199.0144

199.1925

C 13 H'OO2
C13 H2gN
C'3 H '2NO
C'3 H'4N 2
C'3N 3
C'4 H30
C'4 H '40
C'4 H'6N
C'4NO
C'4 H2NZ

198.0681

C'OH23N4
C,oH 7NP
C"H'903
C II H30 4

199.1334
199.0031

C II H2,N02
C II HsN0 3
C II H23 N2O

199.0269

C'3 H902
C'3 H27N
C'3 H II NO
C'3 H '3 N2

197.0603

C II H20 4

197.9953

197.2145

198.1495

197.0841

C II H20N02
C II H4N0 3

198.0191

197.1080

C Il HzzN2 0

198.1733

C'4H29
C'4 H '30

197.2270

C"H6N 20 2
C II Hz4N3

198.0429

C'4H ,sN
C'4 HN 2

197.1205

C'SH'7
C,sHO
C,sH3N
C'6 HS

197.1331

197.0967
197.0104
197.0027
197.0266
197.0391

198

CgH lON20 4
CgH'2N 303
CgH'4N402
C9H,2N04
C9 H'4N 203
C9H'6N30Z

198.0641

C9NP3
C9H,gN 4O
C9H2N40 2

197.9940

C'OH'404
C IO H,6N03
C,oN0 4

198.0892

198.0879
198.1118
198.0766
198.1005
198.1244
198.1482
198.0178
198.1131
197.9827

C'OH,gN 20 2 198.1369
C,oH 2N20 3 198.0065
C,oHzoN3 O 198.1608
C,oH 4N3OZ 198.0304
198.1846
C,oH 2ZN4
198.0542
C,oH6N4O
I
198.1256
C It H,g03

FM

FM

FM

198.1972

198.0317
198.1859
198.2098
198.0794
198.1032
198.1985
198.2223
198.0919
198.1158
198.0093
198.2349
198.1045
198.1284
197.9980
198.0218

C'SH,g
C 15 H2O

198.1409

C,sH 4N
C'6 H6

199.0845
199.1322
199.1560

199.1209
198.9905
199.1447
199.1686
199.0382
199.0621

199.1573
199.1811
199.0508
199.2050
199.0746
199.0985
199.1699
199.0395

198.0344

C'2 H703
C'2 H25 NO

198.0470

C,zH 9N0 2

199.0634
1992176

199.0719

C'ZH 27N2
C1ZHIINP

198.0106

199

CgH'I N204

C"H 7NP2
C IIH2SN3
C II H9N3O
C II H II N4
C'2 H230Z

199.1196

199.1937

199.0872

196

Spectroscopic Data Chemistry


FM

Cl2Hl3N3
C 13 H 2P
C'3 H l102
C'3 H29N
C I3 H 13 NO
C13 H lSN2
C l3 HN 3
C'4 H lSO
CI4H'7N
C l4 HNO

199.1111

FM

FM

200.0460

C 1s H4 O

200.0262

200.2003

C,sH 6 N
C l6 H8

200.0501

C'OH6N3O?
ClOH24N4
CIO H8NP
C ll H200 3

200.1413

201

199.0998

C ll H40 4

200.0109

C8H 13 N20 4

201.0876

199.1236

C ll H22 N02

200.1651

20l.l114

199.0171

C"H6N03
CIIH24N20
C Il H8N z0 2

200.0348

C8H,sN 30 3
C8H'7N402

201.1353

200.1890

C9H 1S N0 4

201.I001

200.0586

201.l240

C ll Hz6N 3
C ll H lON3O

200.2129

C9Hl7N203
C9HN Z0 4

200.0825

201.1478

201.0413

199.2063
199.0759
199.2301

199.1123
199.1362
199.0058

200.0699

200.0626

200.9936

C l4 H3Nz
C 1s H l9

199.0297
199.1488

C ll H 1ZN 4

200.1063

C1sHP
C1sHsN
C'6H7

199.0184

200.1777

199.0422

Cl2Hz302
C l2 H80 3

200.0473

C9Hl9N30Z
C9H3N30 3
C9Hz1 N 4O
C9HsN 4O Z

199.0548

C 1z H26NO

200.2015

C lO H l70 4

201.1 127

C,lH IO N0 2

200.0712

201.1365

ClzHz8N2
CIIHIIN20
C'ZH'4 N 3

200.2254

C IO H l9N0 3
C 1oH3N0 4

201.1604

C l2 N4
C'3 H280
C 13 H 1Z0 2
C l3 H l4NO

200.0124

CIOH21N202
C lO HsN 20 3
C IO H23 N3O
C lO H7 N 3OZ

200.1076

C,oH 2S N4
ClO H9 N4O

201.2081

200.1315

C Il H21 0 3

201.1491

200.0011

CIl HS04

201.0187

200.0249

201.1730

200.1202

C'IH13N~z
C"H 7N0 3

200

C8H'2 N204
C8Hl4N303
C8H'6N402
C9H l4N0 4

200.0797

C9Hl6N203
C9N20 4

200.1162

C9Hl8N30Z
C9 HzN 30 3

200.1400

C9Hzo Np
C9H4N40 2

200.1639
200.0335

C13H'6N2
C l3 NP
C l3 HzN 3

C'OH'604
C'OH I8 N03
C 1oH2N0 4

200.1049

C l4 H l6O

200.1287

C l4 0 Z

199.9898

199.9983

C'4 H I8 N

200.1440

C'4 H2NO
C'4 H4 N2
C,sH zo

200.0136

200.1036
200.1275
200.0923
199.9858
200.0096

CIOH20N202 200.1526
C,oH 4N z0 3 200.0222
C,oH 2ZN 3O 200.1764

200.0950
200.1189
200.2141
200.0837

201.0175
201.1717

201.0062
201.0300
20 I.l 842
201.0539
201.0777

201.0426

CllHzsN10
C ll H9 N zO z

201.1968
201.2207

200.0375

CIIH27N3
C ll H Il N30

200.1566

C Il HJ3N 4

201.1142

201.0664
201.0903

197

Mass Spectrometry

FM

FM

FM

CI2H2S02
C I2 H90 3

201.1855

C IOH 1g0 4

202.1205

C I4 H20N

202.1597

201.0552

C IO H20N0 3

202.1444

C l4 H4NO

202.0293

C I2 H27NO

201.2094

C IO H4N0 4

202.0140

202.0532

C l2 H ll N0 2

201.0790

C I2 H I3 NP

201.1029

CloH22N202 202.1682
C IO H6N 20 3 202.0379

C I4 H6N 2
C 1s H22
C 1s H6O

202.0419

CI2HlSN3
C I2 HN4
C 13 H\302
C I3 H 1SNO

201.1267

202.0657

CI3Hl7N2
C l3 HNzD
C I3 H3N3

202.1921

202.1722

202.2160

201.1154

CIO H26N4
C io H ION4O

C1SHgN
C I6 H IO
203

202.0856

CgHlSN204

203.1032

201.1393

C ll H22 0 3

202.1569

CgHI7N303

203.1271

201.0089

C 11 H60 4

202.0266

203.1509

201.0328

C ll H24N02

202.1808

CgHI9N402
C9 H I7N04

C I4 H I7 O
C I4 H0 2

201.1280

C ll HgN03

202.0504

CIIH26N20

202.2046

C I4 H I9N

201.1519

C9HI9N203
C9H3N 20 4
C9H21N302
C9HsN 30 3

203.1396

200.9976

201.0202
201.0916

CloH24N30
C IO HgN 30 2

202.0617

202.0783

203.1158
203.0093

C I4 H3NO

201.0215

CIIHION202 202.0743
C II H I2N3O 202.0981

C I4 HSN2
C 1s H21

201.0453

C II H I4N 4

202.0122

C9H23 N 4O

203.1873

201.1644

CI2H2602
C I2 H IOO 3

202.1934

C9H7N 40 2

203.0570

202.0630

CloHI904

203.1284

202.0868
202.1107

CloH21N03
CIO HSN 04

203.0218

202.1346
202.0042

CIOH23N202 203.1761
CloH7N203 203.0457

202.0280

C to H2SN 3O

203.1999

202.0994

203.0695

ClsHsO
C 1S H7N
C I6 H9

201.0340
201.0579
201.0705

202
CgHI4NP4
CgHI6NP3

202.0954

CgHIgN402
C9H I6N04

202.1431

202.1193

CI2HI2N02
C I2 H I4NP
CI2HI6N3
C I2NP
C I2 H2N 4

203.1635
203.0331

203.1522

C\3H I4 0 2
C I3 H I6NO

202.1233

CloH9N302
C IO H 11 N 4O

C9HIgN203

202.1318

C\3NO Z

201.9929

C II H23 0 J

203.1648

C9H2NP4
C9Hzo NP2

202.0014

CI3HIgN2
C I3 H2N 2O

202.1471

C II H70 4

203.0344

202.0167

CIIH2SN02
C 11 H9N0 3

203.1886

202.1080

202.1557
202.0253

202.0406

C9H4NP3
C9Hz2N 4O

202.1795

C\3H 4N 3
C I4 H 1gO

202.1358

C9H6N P2

202.0491

C I4 HP2

202.0054

203.0934

203.0583

C 11 HI\N 20 2 203.0821
CIIHI3N30 203.1060

198

Spectroscopic Data Chemistry


FM

C lI H,sN 4

203.1298

C,zH lI 0 3
C,zH 13 N0 2
C'2 H ,sN 2O
C'2 H '7N3

203.0708
203.0947
203.1185
203.1424

FM

C9HgN4OZ
C IO Hzo 0 4
C'OH 22N0 3
C lO H6N04

204.0648
204.1362
204.1600
204.0297

C 13 H'502
C 13 H'7NO

203.1072

C 13 HN0 2

203.0007

C'OH 24 N zO z 204.1839
C IO HgN 20 3 204.0535
C IOH ION 30 2 204.0774
C IO H'2 N40 204.1012
204.1726
C lI H24 0 3
204.0422
ClI Hg04

C 13 H'9N 2
C13 H3N2O
C13 HSN 3

203.1549

C 11 H lON0 3

204.0661

203.0246

C II H'2N 20Z
C"H'4N30

204.0899

C'4H '90
C'4 H302
C'4 H2,N

203.1436

204.1377

203.0133

C lI H'6N 4
C lI N40

203.1675

C'2 H '203

204.0786

C I4 HSNO
C I4 H 7N 2

203.0371
203.0610

204.1025
204.1264

C Is Hz3

203.1801

C 12 H,4N 02
C I2 H,gN 2O
C I2N 20 2

C Is H70

203.0497

C,sH9N
C I6 H lI

203.0736

C 12 HN,G
C'2H 3N 4

203.0120
203.0359
203.1311

203.0484

FM

C'4 H6NO
C'4 HgNZ
C,sH Z4
C'5 HgO

204.0449
204.0688
204.1879
204.0575

C,sHION
C'6 H ,Z

204.0814

C'7
205

204.0000

CgHI7N204
CgH'9 N303

205.1159

204.0939

205.1427

CgH2,N 40 2
C9H I9N04

205.1666

C9H2,N20 3
C9H5N 20 4

205.1553
205.1791
205.0726
205.1440

203.9960

C9Hz3N302
C9H7N 30 3
C9H9N40 2
C lOHzI 0 4
C IO Hz3 N03

204.1502

C lO H7N04

205.0375

204.0198

C lO H9N 20 3

205.0614

204.0437

204.1138
204.0073

205.1315
205.0249
205.0488

205.1679

203.0861

CI2HIgN3
C I2 HzN,G
C I2 H4N4

204.1151

CgHI6N204

204.1111

CI3HI602
C I3 0 3

CloHlIN302 205.0852
C lO H I3 N4O 205.1091

203.9847

C lI H90 4

205.0501

CgHIgN303

204.1349

C 13 H 1gNO

204.1389

CIIHIIN03

205.0739

CgH20N40Z
C9 H IgN04

204.1588

C'3 H2N 02
CI3H20N2
C I3 H4N 2O

204.0085

ClIHI3Nz02 205.0978
CIIHISN30 205.1216

204.0563

204.1713

C I3 H6N 3
C I4 Hzo O

204.0410
204.1952

204

C9H20N203
C9 H4 NP4

C9H2ZN302
C9H6N30 3
C9H I4N 4O

204.1236
204.1475
204.0171

204.1628

205.1455

204.1515

CIIHI7N4
C ll HN 40
ClzHI303

C I4 H4OZ

204.0211

CI2HISN02

205.1103

C I4 HzzN

204.1753

CI2HI7N20

205.1342

204.0324

205.0151
205.0865

199

Mass Spectrometry

FM

FM
C I2 HN Z0 2

205.0038

CI2HI9N3
C 1ZH3N P

205.1580

CIOHION203 206.0692
CloHl2N302 206.0930

205.0277

C 1zHsN4

205.0515

CI3HI702
C I3 H0 3

FM
206.0970

C1sH1zN
C I6 H I4

206.1096

CloHI4N40

206.1169

C I6N

206.0031

206.0579

C l7 H2

206.0157

205.1229

CI1H1OO4
C II H 1ZN0 3

206.0817

207

204.9925

CI1HI4NzOz

206.1056

CgHl9NZ04

207.1345

C I3 H I9NO

205.1467

CgH2,NP3
C9H21 N0 4

207.1584

205.0164

CIIHI6N30
C 11 N3OZ

206.1295

C I3 H3NO z
C'3 H2IN Z
C\3HSNp
C'3 H7N 3

205.1706

C ll H 1gN 4

206.1533

207.0406

205.0402

C II H2N 4O

206.0229

C9H7NP4
C9H9N P3

C9H II N 4OZ 207.0883

C I4 Hz1 O

205.1593

206.1182

C 1oH9N04

C I4 HsOz
C I4 Hz3 N

205.0289

C 12 H'403
CI2HI6NOz
C I2N0 3

206.0943
205.9878

205.1832

C,zH1gNZO

206.1420

CIOHIINz03 207.0770
C 1oH'3 N 30Z 207.1009

C I4 H7NO

205.0528

ClzHzNzOz

206.0116

C I4 H9N 2
C 1s H2S

205.0767
205.1957

CI2HzoN3
C 1z H4N3O

206.1659

C 1s H9O

205.0653

C 1zH6N 4

C1sH11N
C'6 H '3

205.0892

C'3 H lgOi
C'3 H203

C I7 H

205.0078

205.0641

205.1018

206
CgH,gN 20 4

206.1267

CgH20N303

206.1506
206.1744

CgHZ2N402
C9H20N04
C9H2ZNP3
C9H6N Z04
C9HgNP3
C9H ION 4OZ
CloH2204
C 1O HgN04

C\3H 20NO
C I3 H4N0 2
C'3 H2ZN 2

205.9991

206.0355
206.0594
206.1307
206.0003
206.1546
206.0242
206.1784

CioHISN40
C II H 11 0 4

207.1471
207.0644
207.0532

207.1247
207.0657

207.0896
CIIHISN202 207.1134
C II H'7N30 207.1373
C II H I3 N0 3

C II HNP2
C II H'9N4

207.0069

C II H3N4O

207.0308
207.1021

C'ZH'S03
C'2 H'7N 02

207.1611

206.0719
206.1671

C I2 HN0 3

206.1393
206.1631

C\3 H6N P
C\3H gN 3
C I4 H2Z O

CI2HI9N20

206.9956
207.1498

C I4 H6OZ

206.0368

ClzH3N20Z

207.0195

206.0328

C I4 H24N

206.1910

C'4HgNO
C l4 H ION2

206.0606

ClzHzIN3
C I2 HsNp

207.1737
207.0433

C 1z H7N4

207.0672
207.1385
207.0082

206.0566
206.0805
206.1518
206.0453

C 1s Hz6
C1sHIoO

206.0480

206.0845
206.2036
206.0732

CI3HI902
C I3 H30 3

207.1260

Spectroscopic Data Chemistry

200
FM

C I3 Hz1 NO

207.1624

C I3 HsNO z

207.0320

CI3Hz3Nz
C I3 H7NP
C I3 H9N3

207.1863

C I4 Hz3 O

207.1750

C I4 H7OZ

FM

CIIHzoN4
C lI H4NP
ClzHI603
C I2 0 4

208.1690
208.0386
208.1100

Cl2HISNOz
C 1zHzN0 3

207.9796
208.1338
208.0034

207.0446

C I2 H20NP

208.1577

207.1988

CI2H4NzOz

C I4 H9NO

207.0684

CI4HIIN2
C 1sH27

207.0923

ClsHIIO
C 1SH 13 N

20'1.0810

ClzH22N3
C 1zH6N3O
C 1zHsN4
C 13 H20 0 2
C 13 H40 3

208.0273
209.1815
208.0511
208.0750

C I6H 1S

207.1174

C I6 HN

207.0109

C I7 H3

207.0235

C I4 H2S N

207.0559
207.0798

207.2114
207.1049

208

208.1424

CsHzoNz04
C9HsN z0 4

208.0484

C9H ION30 3

208.0723

C9HIZN40Z

208.0961

CioHION04

208.0610

CioHIZNz03

208.0848

CloHI4N30Z

208.1087

CloHI6N40
C 1oN 4OZ

208.1325
208.0022

C 13 H zz NO

C 13 H6 NOz
C 13 H Z4 N z

C I3 HsNp
C I3 H ION3
C I4H z4O
C I4 HsOz
C I4 Hz6N
C I4 H IONO
CI4HIZNz
C1sH zs
C1sHIzO
C 1S HI4 N

C1sN z
208.0735
C I6 H I6
CIIHIZ04
208.0974
C I6 0
CIIHI4N03
CIIHI6NzOz 208.1213 C I6 HzN
207.99-09 C I7 H4
C II N20 3
CIIHISN30 208.1451 209
CIIHzN30Z 208.0147 C9H 9N Z04

208.1464
208.0160
208.1702
208.0399
208.1941
208.0637
208.0876
208.1828
208.0524
209.2067
208.0763
208.1001
208.2192
208.0888
208.1127
208.0062

FM

C9H 11 N,03
C9H13 N40 2

209.0801

C IO H II N0 4

209.0688

209.1040

CIOHI3N203 209.0927
CIOHISN30Z 209.1165
CloHI7N40
C IO HN4OZ

209.1404

C II H I3 0 4

209.0814

CIIHISN03

209.1052

209.0100

CIIHI7NzOz 209.1291
C II HN Z0 3 208.9987
C II H I9N3O
CIIH3N30Z
CIIHzIN4
C 11 HsN4O
ClzHI703
C 1z H04

209.1529
209.0226
209.1768
209.0464
209.1178
208.9874

CIZHI9NOz
C 1z H3N03

209.1416

ClzHzlNzO

209.1655

C1zHsNPz
C 12HZ3 N3

209.0351

C 1zH 7N3O
C 1zH9N 4

209.0590

CI3HzIOZ
C I3 Hs0 3
C 13 HZ3 NO

209.1542

208.1253
207.9949 C I3 H7NO z
208.0187 CI3HzsN2
108.0313 C I3 H9NzO
C13 H II N3
209.0563 C l4 Hzs O

209.0113

209.1894
209.0829
209.0238
209.1781
209.0477
209.2019
209.0715
209.0954
209.1906

201

Mass Spectrometry

FM

FM

FM
C I4 H90 2

209.0603

C I2 HP4

209.9953

C9H\3N 30 3

211.0958

C I4 H27N

209.2145

210.1495
210.0191

C9HISN40Z
C IOH\3N0 4

211.0845
211.1083

211.1196

C I4 H II NO

209.0841

CIZH20NOz
C lz H4N0 3

CI4HI3Nz
C Is Hz9

209.1080

ClzHnNp

210.1733

CioHISNz03

209.2270

C I2 H6NPz

210.0429

C 1S H\30

209.0967

210.1972

CISH1SN
C IS HN 2

209.1205

ClzH24N3
C I2 HsN 3O

CIOHI7N302 211.1322
C 1OHN 30 3 211.0018

209.0140

210.0907

C I6H I7

209.1331

C iz H ION 4
C I3 Hzz 02

CloHI9N40 211.1560
C IO H3N 4O Z 211.0257

210.1620

C II H 1S0 4

C I6HO

209.0027

C\3H60 3
C\3H Z4NO
C I3 HsNO z

210.0317

C II HI7N0 3

211.1209

210.1859

C II HN04

210.9905

210.0555

CIIHI9Nz02

211.1447

C\3H Z6N Z

210.2098

CIIH3Nz03

211.0144

C I3 H 1ONP

210.0794

C\3H 1ZN 3
C I4 Hz6O
C I4 H IOOZ

210.1032
210.0681

CIIHzIN30
C II HsN 30 Z
CIIHz3N4
C I1 H7N 4O

C I4 HzsN

210.2223

C I4H 1ZNO

210.0919

CI4HI4Nz
C I4N 3

210.1158

C IO HzN 4O Z 210.0178
210.0892
C II H I40 4

C Is H30

C II H I6N0 3
C II N0 4

209.9827

CIIHISNzOz

210.1369

CIIHzN203
C II Hz3 N 3O

210.0065

C II H4N3OZ

210.0304

CIIHz2N4
C 11 H6N4 O

210.1846

CI2HIS03

C I6 H3N
C I7 HS

209.0266
209.0391

210

C9H ION Z04

216.0641

C9HIZN303

210.0879

C9HI4N40Z
C\(\HI1N04

210.1118
210.0766

210.0668

210.1985

211.0970

211.1686
211.0382
211.1925
211.0621

ClzHI903
C lz H30 4

211.1334
211.1573

210.0093

CIZH21NOz
C 1z HsN0 3

210.2349

CIZHZ3NzO

211.1811

C 1s H I4 O

210.1045

ClzH7NzOl

211.0508

C 1S HI6N

210.1284

ClsNO

209.9980

ClzHzsN3
C lz H9 N3O

211.0746

ClsHzNz
C I6 H 1S

210.0218

CizHIIN4

211.0985

210.1409

211.1699

C I6 HP
C I6 H4N

210.0106

CI3Hz30Z
C I3 H70 3

211.0395

210.0344

C I3 Hz5 NO

211.1937

210.0470

C\3H9NO Z

211.0634

210.0542

C I7 Ho
211
C9H II Nz0 4

211.0719

C\3H Z7N Z
C I3 H II N zO

211.2176

210.1256

CIOHI4Nz03 210.1005
CIOHI6N30Z 210.1244
C lON 30 3

209.9940

C IO H 1SN 4O

210.1482

210.1131

210.1608

211.0031
211.0269

211.2050

211.0872

202

Spectroscopic Data Chemistry


FM

FM

FM

CJI 13 N3
C I4 H27 O

211.1111

C 11 H22NP

212.1764

C 1SH2NO

211.2063

C 1sH4N 2

212.0375

211.0759

C II H6NP2
C II H24 N4

212.0460

C I4 H Il O2

C I4 H29N

211.2301

C 11 HsN4O

212.0699

C l6 H20
C l6 H4O

212.1566

C I4 H 13 NO

211.0998

212.1413

21 I. 1236

212.0109

C l6 H6N
C l7HS

212.0501

CI4HISN2
C I4 HN 3

CI2H2003
C I2 H40 4

211.0171

213

C,sH3,

CI2H22N02
C'2 H6N 03

212.1651

211.2427

212.0348

213.0876

C1sH1SO
C 1s H l7N

211.1123
211.1362

Cl2H24N20

212.1890
212.0586

C9H'3N 204
C9HlSN303

C,sHNO
C 1s H3N2

211.0058

C16H'9
C'6 HP

211.1488

C'6 HSN
C l7 H7

211.0297

ClzHsN202
ClzH26N3
C l2 H lON3O

212.2003

212.0136

212.0262
212.0626

213.1114

C9Hl7N402

213.1353

212.2129

CioHlSN04

213.1001

212.0825

CloHl7N203 213.1240
C lO HN Z0 4 212.9936

211.0422

C12H'2N4
C 13 H240 2
C l3 Hs0 3

212.0473

CloHl9N302 213.1478
ClOH3N P3 213.0175

211.0548

C 13 H26 NO

212.2015

C,oH2,N4O

213.1717

212.2254

C,oHsN40 2
C II H l7 0 4

2130413

C9Hl2N204

C'3 H ION 02
C'3 H2S N2

212.0712

212.0797

C9Hl4N303

212.1036

212.0950

C II H l9N03

213.1365

C9Hl6N402
C lO H l4N04

212.1275

C 13 H'2 N20
C13H'4N 3

212.1189

C ll H3N04

213.0062

212.0923

C l3N 4

212.0124

C l4 H2S O

212.2141

CIIH21N202 213.1604
CIIHsN203 213.0300

C'4 H '20Z
C'4 H30N

212.0837

C Il Hz3 N3O

213.1842

212.2380

C Il H7N30 2

213.0539

C I4 H,4 NO

212.1076

C Il H2SN4

213.2081

CI4HI6N2
C I4N zO

212.1315

C ll H9N4O

213.0777

212.001 I

213.1491

C'4 HZN 3
C 1s H32

212.0249

C'2 HZI03
C'2 HS04

213.1730

C 1s H l6O

212.1202

CI2H23N02
C l2 H7N0 3

C 1S 0 2

211.9898
212.1440

211.0184

212

C IOH'6N 203 212. I 162


211.9858
C,oN Z0 4
C 1o H,sN 3OZ 212.1400
CloH2N303 212.0096
CloHzoN40
C lOH4N 4O Z

212.1639

C II H'604
C II H 1SN0 3

212.1049

C 11 H2N04

212.0335
212.1287

211.9983
212.1526
CllH20N202
CIIH4N203 212.0222

C1sH1SN

212.1063
212.1777

212.2505

213.1127

213.0187

Cl2H2SN20

213.0426
213.1968

CI2H9N202

213.0664

203

Mass Spectrometry
FM

C13 H2N4
C I4H 30O

214.0280

CI4HI402
C I4 H I6NO

214.0994
214.1233

214.1795

C I4N0 2

213.9929
214.1471

CI2H27N3

213.2207

CizHIIN30

213.0903

ClzHI3N4

213.1l42

CI3H2502
C I3 H90 3

213.1855

CloHzoN30Z 214.1557
CloH4N303 214.0253

213.0552

CloH2ZN40

213.2094

CI3 HnNO
C I3 H II NO z
C13 HZ9N 2
C I3 H13 N ZO

FM

FM

CIOHIgN203
C IO HzN 20 4

214.1318
214.0014

214.2298

CloH6N402

214.0491

213.0790

CIIHIg04

214.1205

213.2332

CIIH20N03
C 11 H4N04

214.1444

CI4HIgN2
C I4 H2NP
C I4 H4N3

214.0140

C I5 H 1g O

214.1358

214.1682

C I5 Hz02
C l5 H20N

214.0054

214.0379
214.1921

C l5 H4NO

214.0293

214.0617

214.0532
214.1722

214.0856

C l5 H6N 2
C J6 H22
C J6 H6O

214.1569

C l6 HgN

214.0657

214.0266

C l7 H IO

214.0783

214.1808

215

214.0504

C9HI5N204

215.1032

214.2046

C9Hl7N303

215.1271

C9Hl9N40Z
C IO H17N04

215.1509

213.1029
213.1267

CI3HI5N3
C l3 HN 4
C l4 H29 O

213.2219

C I4 H 13 OZ

213.0916

C l4 H31 N
C l4 HJ5 NO

213.2458

Cl4HI7N2
C l4 HNP
C l4 H3N 3

213.1393
213.0328

C l5 H l7 O

213.1280

213.0202

213.1154
213.0089

CIIH22N202
C II H6N z0 3
CllH24N30
C II HgN 30 Z
C1JH26N4
C II H ION 4O
ClzHz203
C l2 H60 4
Cl2H24N02
C 1Z HgN0 3
ClzH26N20

214.2160

214.0167
214.0406

214.1597

214.0419

C l5 H0 2

212.9976

C l5 H l9N

213.1519

C l5 H3NO

213.0215

Cl2HION202 214.0743
214.2285
Cl2H2gN3

C l5 H5N 2
C l6 H21

213.0453

CJZH12N30

214.0981

CIOH19N203

215.1396

213.1644

Cl2HI4N4

214.1220

CJOH3NZ04

215.0093

C J6 HSO

213.0340
213.0579

214.0630

CIOHzIN302
C IO H5N 3O)

215.1635

C J6 H7N
C J7 H9

Cl3Hz60Z
C J3 H IO O3

214.1934

213.0705

C J3 H2g NO

214.2172

C IO H23 N 4O

215.1873

C'3 H ,zNO z

214.0859

C IO H7N 4OZ 215.0570

214.2411

214

215.1158

215.0331

C9HJ4NZ04
C9H'6N303

214.0954
214.1193

C13 H30N 2
C'3 HI4N ZO

C9HlgN402

214.1431

C'3 H16N 3

214.1345

C II H'904
C 11 Hz,N03
C II HsN04

C IO H,6N 04

214.1080

C'3 N P

214.0042

CIIHz3N202 215.1761

214.1107

215.1284
215.1522
215.0218

204

Spectroscopic Data Chemistry


FM

C"H 7N 20 3
C II H2S N 3O

215.0457

C,sH 7N 2
C I6 H23

215.0610

C II H9N 30 2

215.0695

C II H27N4

215.2238

215.0497

215.0934

C'6 HP
C I6 H9N
C'7 H II

C II H II N 40
CI2Hz303
C I2 H70 4

215.1648

216

215.0344

C9HI6N204
C9H,sN 30 3

215.1999

CI2H2SNOz
C lz H9N03

215.1886

CIZH27NzO

215.2125

215.0583

FM

FM

C9H20N402
C IO H jSN04

215.1801
215.0736

C'2 H '6N 4
C I2NP
C 13 H2S 0 2

216.1377
216.0073
216,2090
216.0786

C 13 H'203
C 13 H I4N0 2

216.1025

C 13 H I6N zO

216.1264
215.9960

216.1588

C'3N Z02
CI3HISN3
C'3 HZN30

216.1236

215.0861
216.1111
216.1349

216.1502
216.0198

C13 H4N4

216.0437

ClzHIIN20Z 215.0821
215.2363
ClzH29N3

CIOHzoNz03 216.1475
CIO H4N Z04 216.0171

CI4HI60Z
C I4 0 3

216.1151
215.9847

C lz H'3 N 30
C'2 H IS N4

215.1060

C I4 H 1SNO

216.1389

215.1298

CIOHz2N30Z 216.1713
CloH6N303 216.0410

C I4 H2N02

216.0085

C 13 HZ7 OZ

215.2012

C IO H24N 4O

216.1952

216.1628

C'3 H IP3
C'3 HZ9NO

215.0708

CIO HSN402
C II Hzo 0 4

216.0648

CI4H20Nz
C I4 H4N 2O

216.0324

C II Hz2N0 3

216.1600

C I4 H6N 3
C 1s H20O

216.0563
216.1515

215.1185

CII H6N04

216.0297

C 1s H40 2

216.0211

215.1424

C I3 HNP
C I3 H3N 4

CIIHZ4NzOz 216.1839
C'I HSN z03 216.0535

C IS H2ZN
C IS H6NO

216.1753

215.0120
215.0359

C II H26N3O

216.0688

CI4HISOZ
C'4 H I7NO

215.1072

C II H wN30 2 216.0774

C Is HsN2
C'6 H24

215.1311

C II Hzs N4

C I4 HNO Z

215.0007

C'I H ,zN4O

C I4 H"N z
C'4 H3N20

215.1541

C I4 HSN3

215.0484

C'SH'90
C Is H30 Z

CI3HI3N02
C I3 H,sN 2O
C 13 H'7N 3

C1sHz1N
C,sHsNO

215.2250
215.0947

216.1362

216.2077

216.0449
216.1879
216.0575

216.2316
216.1012

C I6 HsO
C I6 H ION

C'2 HZ403
C,zHS0 4

216.1726

216.0939

215.1436

ClzH26N02
C I2 H ION03

216.1965

C'7 H 12
CIS
217

216.0661

C9HI7Nz04

217.1189

215.0133

CI2H2SNzO

216.2203

C9HI9N303

217.1427

215.1675

CI2HI2N202 216.0899
CI2HI4N30 216.1138

C9H21N402
C lO H I9N0 4

217.1666

215.0246

215.0371

216.0422

216.0814
216.0000

217.1315

205

Mass Spectrometry
FM

FM

CIOHzINz03 217.1553
CIO H5N Z04 217.0249

FM

C I4 H I9NO

217.1467

CIIHI4N40

218.1169

C I4 H3N0 2

217.0164

ClzH2603

218.1883

CI4HzIN2

217.1706

CI2HIOO4

218.0579

217.0402

CI2HI2N03

218.0817

217.2030

CI4H5NzO
C I4 H7N 3

217.0641

C IO H9N4OZ

217.0726

C I5 H21 O

217.1593

CI2HI4N202 218.1056
C 12H'6N 30 218.1295

C\lH2I 0 4

217.l440

C I5 H50 2

217.0289

C I2N30 2

217.9991

CIIH23N03
C\lH7N04

217.1679
217.0375

C I5 Hz3N

217.1832
217.0528

C'ZH1SN.
C I2HzNp

218.1533

C I5 H9N2
C I6 Hz5

217.0767

C\3H I40 3

217.1957

C I6 HP
C'6 H II N

217.0653

C\3H I6N0 2
C I3N0 3

217.0892

C\3H 1gN ZO

C I7 H I3

217.1018

CI3H2N202

217.0078

CI3H20N3
C'3 H4N P

CloH23N30Z 217.1791
CloH7N303 217.0488
C IOH25 N4O

C\lHZ5N 20 4 217.1917
C\lH9N 20 3 217.0614
C II Hz7N3O 217.2156
CIIHIIN302 217.0852
C"H\3N 4O 217.1091

C I5 H7NO

C II HZgN 4

216.2316

CI2H2503
C I2 H90 4
CIZH27NOz

217.1804

C,sH
218

217.0501

C9HIgN204

218.1267

C9H20N303

218.1506
218.1744

217.2043
CI2HIIN03 217.0739
C 12H'3N 202 217.0978
C 12H'5N 30 217.1216
217.1455
CI2HI7N4
C 12HNP

217.0151
217.0865

CI3HI~03
C\3H I5NO Z 217.1103
C\3H'7N 20 217.1342
C'3 HN 20Z

217.0038

C13 H I9N3
C'3 H3N 30

217.1580
217.0277

C'3 H5N4

217.0515
217.1229

C'4 H'70Z
C'4 H03

216.9925

C9H2ZN40Z

218.1393
218.1631
CIOH22N203
C,oH6N 20 4 218.0328
CloHz4N302 218.1870
CloHzoN04

CIOHgN303

218.0566

CloH26N40 218.2108
C IO H,oN40 2 218.0805
218.1518
C\lH 2Z 0 4

218.1757
218.0453
C'IHgN04
CIIHZ6NzOz 218.1996
C"H,oN20 3 218.0692
C II H'2 N 30Z 218.0930
C"H Z4N03

C I3 H6N4
C'4 H IS02
C I4H20 3

218.0229
218.0943
218.1182
217.9878
218.1420
218.0116
218.1659
218.0355
218.0594

C I4 H20NO

218.1307
218.0003
218.1546

C I4 H4N0 2

218.0242

C'4 H22N 2
C'4 H6N ZO
C I4 HgN3
C I5 Hz2 O

218.1784
218.0480

C'5 H602
C'5 H24N

218.0368
218.1910

C'5 HgNO
C'5 H ,oN 2
C'6 H26

218.0606
218.0845
218.2036
218.0732
218.0970

C'6 H ,OO
C'6 H ,zN

218.0719
218.1671

206

Spectroscopic Data Chemistry

FM
C'7 H '4
C'7N
C'8 H2

218.1096
218.0031
218.0157

219

C9H'9N204
C9H2,N 30 3
C9H23N402
C IO H2,N04

219.1345
219.1584
219.1822

219.1471
C'OH23 N20 3 219.1710
C IO H7N20 4 219.0406
C,oH 2S N30 2 219.1948
C IO H9N30 3 219.0644

FM
CI3 HsN P
C13 H7N4
C'4 H '902
C'4RP3
C'4 H2,NO
C'4 HSN 02
CI4H23N2
C'4 H7N P
C I4 H9N3
C'SH23 O
C,sH70 2

C IOH lI N 40 2 219.0883

C,sH 2SN
C 1S H9NO

219.1597

C is H lI N2

219.1835
219.0532

C'6H27
C I6 H"O
C'6H 13N
C'7 H ,S

C"H 23 0 4
C lI H2SN0 3

C"H9N04
C'I H 'I N 203 219.0770
C,lI'3 N302 219.1009
219.1247
C 1,H,sN4o
C I2 H II 0 4
219.0657
C'2 H'3 N 03 219.0896
C'2 H,sN20 2 219.1134
C'2 H'7N30 219.1373
C I2 HN 30 2
C'2 H9N4
C I2 H3N 4O

219.0069
219.16II
219.0308

C 13 H 1S 0 3

219.1021

C'3 HI7N 02
C I3 HN0 3

219.1260

CI3HI9NzO
C 13 H3N 20 2
C13 H21 N3

218.9956
219.1498
219.0195
219.1737

219.0433

FM

219.0672

C II H'4N30Z 220.1087
C"H'6N40 220.1325

219.1385

C IIN 40 2

220.0022

219.0082

C'2 H '204
C'2 H'4N 03

220.0735'

219.1624
219.0320
219.1863

220.0974

C 12H'6N202 220.1213
C I2N20 3
219.9909

220.1451

219.1750

C'2 H ISN30
CI2H2N302
C'2 H20N4

219.0446
219.1988

C'2 H4N40
C'3 H '603

219.0684

C'304
C'2 H ,sN02
C 13 H2N0 3

220.0386
220.1100
219.9796

219.0559
219.0798

219.0923
219.2114
219.0810
219.1049
219.II74

C'3 H20N20
C'3 H4N P2

220.0147
220.1690

220.1338
220.0034
220.1577
220.0273
220.1815

219.0109
219.0235

C'3 H22N3
C I3 H6NP
C13 HSN4

220.1464

C9H20N204

220.1424

C'4H2002
C I4 H40 3

C9HzzN303

220.1662

C I4 H2ZNO

220.1901
C'OH 22N04 220.1549
CloH24N203 220.1788
CloHsN204 220.0484
CIOHION303 220.0723

C I4 H6N02

220.1702
220.0399 -

C I7HN
C 1s H3
220

C9H24N402

220.0511
220.0750
220.0160

CI4H24N2
C I4 HsNp
CI4HION3
C 1s H24 O

220.1941
220.0637

CIOHI2N402 220.0961
C II H24 0 4
220.1675

C is Hs02
C 1S HZ6N

220.0524

220.0610
CIIHI2N203 220.0848

C1sHIoNO

CIIHION04

CIsHI2Nl

220.0876
220.1828
220.2067
220.0763
220.1001

Mass Spectrometry

207

FM

C'6 H2S
C'6 H '20

220.2192
220.0888

C 13 H2,N 2O
C'3 H5N202

221.1655
221.1894

C II H'6N302 222.1244
221.9940
C 1,N 30 3
C II H,sN 4O 222.1482

221.0590

C II H2N40 2

222.0178

221.0829

C'2 H '404
C'2 H '6N 03

222.0892

C'2N 04
C'2 H,sN20 2
C'2H 2N20 3
C'2 H20N30
C'2 H4N302

221.9827

221.0351

C,p

219.9949

C'3 H23 N3
C'3 H7N 30
C13 H9N4
C'4 H2,02

C'7 H2N
C,sH 4
221

220.0187

C'4 H503

221.0238

220.0313

C'4 H23 NO
C'4 H7N02
C'4 H25N2

221.1781

C'6 H '4N
C'6N 2
C'7 H '6

C9H2,N 20 4
C9H23 NP3
C IO H23 N0 4
C IO H9N20 4

220.1127
220.0062
220.1253

221.1502
22l.l741
22l.l628
221.0563

CIOHII~303
C IO H13'N 40 2 221.1040
C II H II N04 221.0688
C II H13 N20 3 221.0927

221.0801

221.1542

221.0477
221.2019

C'4 H9N20
C'4 H II N3

221.0715

C'5 H250
C'5 H902
C'5 H27N
C'5 H II NO

221.1906

221.0954
221.0603
221.2145
221.0841

CII H'7 N40


C II HN 40 2
C'2 H 1304

221.0100
221.0814

C'5 H '3 N2
C'6 H29
C'6 H13 0
C'6 H '5N
C'6 HN 2

C'2 H '5N03

221.1052

C'7 H '7

221.1331

C'2 H'7N202
C'2HN203
C'2 H '9N30

221.1291

C'7 HO
C'7 H3N

221.0027

C,sH5
222

221.0391

C II H'5N302 221.1165

C'2 H3NP2
C'2 H2,N 4
C'2 H5NP
C'3 H '703
C'3 H04
C'3 H '9N02
C 13 H3N0 3

22l.l404

220.9987
221.1529
221.0226
22 l.l 768

221.1080
221.2270
221.0967
221.1205
221.0140

221.0266

222.0065
222.1608
222.0304
222.1846
222.0542
222.1256

C'3 H204
C 13 H20NO.2
C'3 H4N03

221.9953

C'3 H22N20
C'3 H6N202

222.1733

C'3 H24N3
C'3 HSN30
C'3 H ION4

222.1972

C'4 H2202
C'4 H603
C'4 H24NO
C'4 HSN02

222.1495
222.0191
222.0429
222.0668
222.0907
222.1620
222.0317
222.1859
222.0555

222.0879
222.1118

C 1s H26 O

222.1985

222.0766

C I5 H,002
C'5 H2SN

222.068\

221.0113

C II H I4 N2O;

222.1005

220.9874

222.1369

222.0794

221.1416

221.1178

C'2 H22N4
C'2 H6N40
C'3 H 'S03

222.1131

C'4 H26N2
C'4 H ,oN 2O
C'4 H '2N3

222.1580

C9H22N204
C IO H ION20 4
C IOH'2N303
C IO H'4 N402
C II H,2 N04

221.0464

FM

FM

222.0641

222.2098
222.1032

222.2223

208

Spectroscopic Data Chemistry

FM

FM

FM

C 1S HI2 NO

222.0919

C I3 H30 4

223.003 J

CIOHI4N30J

CIsHI4N2
C 1s N 3

222.1158

223.1573

222.0093

CI3HzIN02
C I3 HSNO J

ClOHI6N402 224.1275
CIIHI4N04 224.0923

C I6 H30

222.2349

CI3H23N20

223.1811

C I6 H I4 O

222.1045

CI3H7Nz02

223.0508

C I6 HI6 N

222.1284

223.2050

C I6 NO

221.9980

CI3H2SN3
C\3H 9N JO

223.0746

CIIHISN302 224.1400
C II H2N30 3 224.0096

C I6 HzN2

222.0218

CI3HIIN4

223.0985

C II H20N 4O

224.1639

C I7 H 1S

222.1409

223.1699

C II H4N40 2

224.0335

C I7 HP
C I7 H4N

222.0106

CI4H2302
C I4 H70 3

223.0395

Cl2Hl604

224.1049

222.0470

C l4 H2S NO
C l4 H9N02

223.1937

C 1sH6

CIZHlSNOJ
C I2 H2N04

223.9983

223

CI4H27N2

223.2176

CIOHIIN204 223.0719
C IO H\3N 30 3 223.0958
CIOHISN402 223.1196

Cl4HIINzO
C I4 H\3N 3
C 1s H27 O

223.0872

Cl2H20N202 224.1526
Cl2H4N203 224.D222

223.1111

CI2H22N30

224.1764

223.2063

Cl2H6N302

224.0460

ClsHIIO Z
C 1s H29N

223.0759

CI2H24N4
C 1zHsN4O
CI3H200J
CJ3H 40 4

CIIHl3N04

222.0344

223.0845

CIIHl5N20J 223.1083
C II H l7NP2 223.1322
223.0018
C 11 HNP3

C1SH1JNO

223.0269

223.0634

223.2301

..

223.0998
223.1236

224.1036

CIIHI6N203 224.1162
223.9858
C 11 N z0 4

224.1287

224.2003
224.0699
224.1413
224.0109

223.0257

Cl5HI5N2
C1sHN J
C I6 H31

223.0970

C I6 H I5 O

223.1123

223.1209

223.1362

222.9905

C l6 HI7N
C l6 HNO

C\3H 22N0 2
C l3 H6N0 3
,CIJH24N20
CJ3H gN 20 2

223.0058

CJ3H26N3

224.2129

CI2Hl9N202 223.1447
CI2H3N203 223.0144

C I6 H3N 2
C l7 H I9

223.0297

CJ3H ION JO

224.0825

223.1488

C\3H I2N4

224.1063

223.0184

CI4H2402
C I4 Hs0 3
C I4 Hz6NO

224.0473

C I4 H ION0 2

224.0712

CI4H2SN2

224.2254

CIIHI9N40
C ll H3N 40 2
CI2Hl504
Cl2Hl7NOJ
C I2 HN0 4

223.1560

CI2HzIN30

223.1686

CI2H5N30Z

223.0382

CIZH2JN4
C 1z H7N 4O

223.1925

C\3H I9 0 3

223.1621
223.1334

C I7 HP
C I7 H5N
C 1s H7
224

223.0171
223.2427

223.0422
223.0548

CIOHIZNz04 224.0797

224.1651
224.0348
224.1890
224.0586

224.1777
224.2015

209

Mass Spectrometry

C14HI2N20

224.0950

C12H1704

225.1127

C14HI4N3
C 14N4

224.1189
224.0124

CI2H19N03
C I2 H3N04

C 1s H2S O

224.2141

ClsHI202
C 1s H30N

224.0837

C12H21N202 225.1604
C12HsN203 225.0300

C 1S HI4NO

224.1076

CIsHI6N2

224.1315

C1sNP
C 1sH 2N 3

224.0249

224.2380

224.0011

C I6 0 2

224.2505
224.1202
223.9898

C I6H 1SN

224.1440

C I6H 2NO

224.0136

C I6 H32
C I6H I6O

C I6 H4N 2
C I7 H20

224.0375

C I7 H4O

224.1566
224.0262

C I7 H6N

224.0501

224.0626
C1sHs
225
C IO H 13N 20 4 225.0876
CIOHISN303 225.1114
CIOHI7N402 225.1353
CI\H 1SN0 4 225.1001
CIIHI7N203 225.1240
C 11 HN 20 4 224.9936

225.1365
225.0062

225.0328
225.2584

C I6 H 1P
C I6 H02

225.1280

C I6 H 19N

225.1519

224.9976

225.1842

C 16H3NO

225.0215

225.0539

225.0453

CI2H2SN4
C 12H9N 4O

225.2081

C I6 HSN2
C I7 H21

225.0340

225.1491

C I7 HP
C I7 H7N

225.0187

C 1s H9

225.0705

226

C I3 H7N0 3

225.1730
225.0426

CI3H2SN20
C 13 H9N 20 2

225.1968
225.0664

C13 H27N 3
C 13 H 11 N 3O

225.2207
225.0903

C I3 H 13 N 4

225.1142

CI4H2S02
C I4 H90 3

225.1855

CI3H2103
C13 H S04
C 13 H23 N02

C I4 H27NO
C14HIIN02

225.0777

225.0552
225.2094
225.0790
225.2332
225.1029

CI4H29N2
C I4H 13N 2O
CI4HISN3
C I4 HN4

225.0202

225.1267

C 1s H29O

225.2219

225.1478

C 1S H I3 0 2

225.0916

CllH3N303

225.0175
225.1717
225.0413
224.9936

C 1s H31 N
C 1s H1SNO

CllHsN402
C 11 HN Z0 4

C 1s H3N3
C 16H33

C I2 H23 N
CI2H7N302

C 11 HI9NP
CllH21N40

FM

FM

FM

ClsHI7N2
C 1S HN2O

225.1644
225.0579

CIOHI4N204 226.0954
CIOHI6N303 226.1193
CloHISN402 226.1431
C 1I H I6N0 4 226.1080
C1IHISN203
C 1I H2N20 4

226.1318
226.0014

Cl1H20N302 226.1557
CIIH4N303 226.0253
C 1I H22N4 O
C 1I H6N 40 2
CI2HIS04
CI2H20N03
C I2 H4N04

226.1795
226.0491
226.1205
226.1444
226.0140

CI2H22N202 226.1682
CI2H6N203 226.0379

225.2458

C12H24N30
C 12 HgNP2

226.1929
226.0617

225.1154
225.1393
225.0089

C12H26N4
C 12 H ION4O

226.2160
226.0856
226.1569

C13H2203

Spectroscopic Data Chemistry

210
FM

C'3 H604
C 13 H24 N02
C'3 HSN03
C 13 H26N 2O

C'4 HzsNO
C'4 H'2 N OZ

FM

226.0419

227.2012

226.1808

C'7 H60
C'7 HSN

Cl4H2702
226.0657. C'4 H I,03

227.0708

226.0504

C,sH IO

226.0783

227

C'4 H29NO
C'4 H I3 N02
C'4 H3,N2
C'4 H,sNzO

227.2250

226.2046

227.1424

226.0266

C 13 H ION20 2 226.0743
C'3 HZS N3
C 13 H,zN 3O
C'3 H '4N4
C'4 HZ602
C'4H IOO3

FM

226.2285

C IOH,sN 20 4 227.1032
C IOH'7 N303 227.1271
227.1509

227.0947
227.2489
227.1185

C IO I-i'9N402
C II H,7N04
C II H'9N203
C II H3Nz0 4

227.1158
227.1396
227.0093

C'4 H '7N3
C l4 HNP
C'4 H3N4
C,sH3,O

226.2172

C II Hz,N30 2

227.1635

C,sH,sOz

227.1072

226.0868

C'SH33N
C'SH'7NO

227.2615

226.0981
226.1220
226.1934
226.0630

227.0120
227.0359
227.2376

C'4 H30N Z
C'4N '4N 20

226.2411
226.1107

C"H sN 30 3 227.0331
C II Hz3N4O 227.1873
C II H7N4OZ 227.0570

226.1346

227.1284

C,sHNO z
C'SH'9NZ

227.0007

C'4H '6N3
C'4N30
C'4 HZN 4

226.0042

227.1522

C,sH3NP

227.0246

227.0218

C,sH30O

226.2298

227.0484
227.1436

C'SH'402
C,sH 32N
C'SH'6 NO

226.0994

C'ZH 23N 20 2
C'2 H;NP3 227.0457
C'2 H2S N30 227.1999
C'2 H9N302 227.0695

C,sHsN3
C'6 H '90
C'6 H30Z
C'6H2,N
C'6 HSNO

227.0133

C,sN02

225.9929

227.2238

226.1471

C,sH 2NP
C,sH 4N 3
C'6 H34

226.0167

C'6H7N2
C'7 H23
C'7 HP

227.0610

C,sH,sN2

C'2 H27N4
C'2 H II N40
C'3 H2303
C'3 H704
C 13 H2S N02

227.0344

227.0736

227.1886

C'7 H9N
C,sH II

C'6 H ,SO
C'6 H202
C'6H 20N
C'6 H4NO
C'6 H6N2

226.1358

227.0583

228

227.2125

226.1597
226.0293

C'3 H9N03
C'3 H27N20
C 13 H II N20 2
C'3 H29N3

226.0532

C13 H 13 N30

227.1060

C lOH'6N 204 228.11 II


C IO H,sN 30 3 228.1349
CIOH20N40Z 228.1588
C II H,sN04 228.1236

C'7 HZ2

226.1722

C 13 H,sN4

227.1298

CI,H20N203 228.1475

226.0280

226.2536
226.1233

226.0406
226.2662
226.0054

C'ZH'904
C 11 Hz,N03
C'2 HSN 04

227.1761

227.0934
227.1648

227.0821
227.2363

227.131 I
227.1549

227.1675
227.0371
227. I 801
227.0497
227.0861

211

Mass Spectrometry
FM

C Il H4N20 4

228.0171

C Il H22NP2 228.1713
C Il H6N 30 3 228.0410
C Il H24N 4O

228.1952

CIl HSN402

228.0648

CI2H2004

228.1362

FM

C I4 H2N3O

228.0198

C I4 H4N 4

228.0437

C Is H320

228.2454

CIsHI602
C IS 0 3

227.9847

228.1151

FM

CI2H23N03
C I2 H7N0 4

229.1679
229.0375

C lz H2S NP2 229.1917


CI2H9N203 229.0614

228.0085

CI2H27N30 229.2156
C I2 H Il NP2 229.0852
229.2394
ClzH29N4

CIsH20N2
C IS H4NP
C Is H6N 3

228.1628
228.0324

CI2HI3N40
C I3 H25 0 3

229.1091

228.0563

C I3 H90 4

229.0501

228.2077

C I6H20O

228.1515

C 13 H27N0 2

229.2043

CI2HION302 228.0774
228.2316
CI2H2SN4
CI2HI2N40 228.1012

C I6 H40 2

228.0211

CI3HIIN03

C I6 H22N

228.1753
228.0449

229.0739
229.2281

CI3H29NzO
C 13 H13 N 2OZ 229.0978
229.2520
CI3H31N3
C 13 H ISN3O 229.1216

CI2HzzN03 228.1600
C I2 H6N04 228.0297
ClzH24Nz02 228.1839
CI2HsN203 228.0535
C I2 Hz6NP

C 13 H24 0 3

228.1726

C13 HS04
C 13 H26N0 2

228.0422

ClsHlsNO
C Is HzN0 2

C I6 H6NO

228.1389

229.1804

C I6 HSN2
C I7 H24

228.0688

C I7 HsO

CI3H2SN20

228.1965
228.0661
228.2203

C Is H I2

228.0575
228.0314
228.0939

CI3HI2N202
C13 H30N 3

228.0899
228.2442

C I9

228.0000

229

CI4H2902
C I4 H I3 0 3
C I4 H31 NO

229.0865
229.2407

C 13 HI4N 3O

228.1138

C IO H17N 20 4 229.1189

CI4HISNOz

229.1103

C13 HI6N4
C I3 HP

228.1377
228.0073

CloHI9N303

229.1427

CI4HI7N20

CI4H2S02

229.1666
229.1315

C I4 HNPz

228.2090

CIOH21N40Z
C Il H I9N04

229.1342
229.0038

CI4HI203
C I4 H30NO

228.0786
228.2329

CIlH21N203
C Il HsN 20 4

229.1553
229.0249

CI4HI4N02

228.1025
228.2567

CIIH23N302 229.1791
C Il H7N30 3 229.0488

228.1264
227.9960

CIIHzsN40
C Il H9N 4OZ
ClzH2104

C 13 H ION0 3

CI4H3ZN2
CI4HI6N20
C I4N 20 2
CI4HISN3

228.1502

C I7 H ION

228.1879

C13 HI7N4
C I3 HN 4O

Cl4HI9N3
C I4 H3N3O
C I4 HSN4

229.1455
229.0151
229.2168

229.1580
229.0277
229.0515
229.1229

229.2030
229.0726

CIsHI702
C Is H0 3
C IS H I9 NO
C 1s H3N0 2

228.9925
229.1467

229.1440

CISH21Nz

229.1706

229.0164

212

Spectroscopic Data Chemistry

FM

FM
230.1883

ClsHsNzO
C ls H7N3

229.0402
229.0641

Cl3Hz603
C 13 H lOO4

C l6Hzl O

229.1593

C I6 Hs02
C l6 Hz3 N

229.0289

C 13 HZSNO Z 230.2121
C 13 H1Z N0 3 230.0817

229.1832

C l6 H7NO

229.0528

C l6 H9Nz

229.0767

C13 H30NZO 230.2360


C l3 H l4NPz 230.1056
Cl3Hl6N30 230.1295

C I7Hzs
C l7 H ll N

229.1957

C 13 N3OZ

229.9991

229.0892

CI3HlSN4
C 13 HZN4O

230.1533

Cl4H300Z
Cl4Hl403
CI4HI6NOz
C I4N0 3

230.2247
230.0943

C I7 H9O
C lS H I3
C l9H
230

229.0653
229.1018
229.0078

ClOHlSNz04 230.1267
ClOHzoN303 230.1506
CIOHzzN40Z 230.1744
CIIHzoN04 230.1393
CIlHzzNz03 230.1631
C II H6Nz0 4

230.0328

CIIHz4N30Z 230.1870
C II HsN 30 3 230.0566
C II Hz6N4O

230.2108

CIIHION40Z 230.0805
230.1518
ClzHzz04
ClzHz4N03 230.1757
C lz HsN0 4 230.0453
CIZHZ6NzOz 230.1996
ClzHlONz03 230.0692
ClzHzsN30

230.2234

ClzHI2N30Z
C lz H 30N 4

230.0930
230.2473
230.1169

ClzHI4N40

CI4HlSNzO
CI4HzNzOz
CI4HzoN3
C l4 H4N3O
C I4 H6N4

230.0579

230.0229

230.1182
229.9878
230.1420
230.0116
230.1659
230.0355
230.0594

ClsHlsOz
C ls Hz0 3

230.1307
230.0003

C1sHzoNO
C 1SH4NO z

230.1546

ClsHzzNz
C 1S H6NzO
C 1sHsN3
C l6 Hzz O

230.1784
230.0480

230.0242

FM
230.0732

C l7 H lOO
C l7 HlZN

230.0970

C ls H l4

230.1096

ClsN
C I9 Hz

230.0031
230.0157

231

CloHl9Nz04 231.l345
CloHzlN303 231.l584
CloHz3N4OZ 231.1822
C ll Hzl N04 231.l471
CllHz3Nz03 231.17lO
C ll H7NZ04
CllHzsN30Z
C Il H9N30 3
C ll Hz7N4O

231.0406
231.l948
231.0644
231.2187

C Il H Il N40 Z 231.0883
231.1597
ClzHz304
ClzHzsN03
C lz H9N04

231.1835
231.0532

CIZHZ7NzOz 231.2074
C,zH II N z0 3 231.0770
ClzHz9N30 231.2312
ClZH13N30Z 231.l009
CizHISN40 231.1247

230.0719
230.1671

C I3 H270 3
C I3 H II 0 4
C I3 H29NO z

231.l961
231.0657
231.2199

C I6 H6OZ

230.0368

C I3 H 13 N03

231.0896

C I6 H24N
C I6 HSNO

230.1910
230.0606

231.l134

C I6H lONz
C I7 Hz6

230.0845
230.2036

CI3HISN202
CI3HI7N30
C I3 HNPz
C13 H I9N4

231.1373
231.0069
231.1611

Mass Spectrometry

213

FM

FM

FM

C ll H24NP3 232.1788
C ll HgNZ0 4 232.0484

ClsH2002
C ls H4 0 3

232.1464

C ls H2ZNO

232.1702

230.9956

CllHz6N30Z 232.2026
C ll H lON30 3 232.0723

C ls H6 N0 2

232.0399

C l4 H l9NP

231.I498

CllHzsNp

232.2265

C l4 H3NP2
Cl4H2lN3
C l4 HsNp

231.1737

CllHl2N40Z 232.0961
232.1675
Cl2Hz404

ClsH24N2
C ls H,N 2O
C is H lON 3

232.1941

231.0195

232.1914

C l6 H24O

232.1828

C I4H7N.

231.0672

232.0610

ClsHl90Z
C ls H30 3

231.1385

C l6 Hs02
C l6H 26N

232.2067

C l6 H lONO

232.0768

C l3 H3N4O

231.0308

C14HlS03

231.1021

Cl4Hl7NOz
C l4 HN0 3

231.1260

231.0433

231.0082

ClzH2SNzOz 232.2152
ClzHl2Nz03 232.0848

232.0637
232.0876
232.0524

C l2 Hl4NPz
C lz HI(jN4O

232.1087
232.1325

Cl6Hl2Nz
C 17 H28

232.1001

231.0320
231.1863

C lzN 40 Z

232.0022

C l7 H lZ O

232.0888

231.0559

C 13 HZS 0 3

232.2039

C l7 Hl4N

232.1127

231.0798

C 13 H I2 0 4

232.0735

C l7N z

232.0062

291.1750

C I3 H14N03

232.0974

ClsH 11i

232.1253

C l6 H7O Z

231.0446

CISO

231.9949

C l6 Hzs N
C l6H 9NO

231.1988

C I3 H"N zOz 232.1213


C 13 N20 3
231.9909

ClsHzN
C l9 H4

232.0187

ClsHzlNO
ClsHsNO z
ClsHz3Nz
C ls H 7NP
C ls H9N3
C l6 Hz3 O

231.1624-

ClzHz6N03
C lz H lON04

232.0160

231.0684

C I6 H ll Nz
C 17HZ7
C I7 H ll O

231.0923

C I7 H 13N

231.1049

CIsH 1S

231.1174

C1sHN
C'9H 3

231.0235

231.2114
231.0810

231.0109

232
CIO H20N Z04 232.1424
CIOHz2N303 232.1662
ClOH24N402 232.1901
, C II H22N04 232.1549

Cl3HlSN30
CI3HzN30Z
C13 HZON4
C 13 H4N4O
CI4HI603
C I4 0 4
CI4HIXN02
C I4 HzN0 3
C'4 HZON 20
C'4 H4N20Z
CI4H2ZN3
C I4 H6N 3O
C I4 HSN4

232.1451
232.0147
232.1690
232.0386
232.1100
231.9796
232.1338
232.0034
232.1577
232.0273
232.1815
232.0511
232.0750

232.2192

232.0313

233
CloHzINz04 233.1502
ClOHz3N303 233.1741
CloHzsN40Z 233.1979
C ll Hz3 N0 4 233.1628
CllHzsNz03
C Il H9N z0 4

233..1866
233.0563

CllH27N30Z 233.2105
CIlHIIN303 233.0801
C ll H 13N 40 2 233.1040
233.1753
CI2H2S04
Cl2H27N03 233.1992

214

Spectroscopic Data Chemistry


FM

C iz H Il N04

233.0688

FM

FM

C I6 H 11 NO

233.0841

C 13 H4N3 OZ 234.0304

ClzHI3Nz03 233.0927
C1zH1sNPz 233.1165

CI6HI3Nz
C I7Hz9

233.1080

CI3HzzN4
C I3 H6NP

234.1846

ClzHI7N40
C 1ZHN 4OZ

233.1404

C I7 H I3 O

233.0967

234.1256

233.0100

C I7 H 1S N

233.1205

CI4HIS03
C I4 Hz04

C I3 H I3 0 4

233.0814

C I7HNZ

233.0140

234.1495

C 13 H1S N03

233.1052

C 1sH I7

233.1331

CI4HzoNOz
C I4H4N0 3

234.0191

ClsHO
C 1S H3N
C I9 HS

233.0027

C I4 Hzz Np

234.1733

233.0266
233.0391

CI4H6N20Z

234.0429
234.1972

CI3HI7Nz02 233.1291
C 13 HNZ0 3 232.9987
CI3HI9N30 233.1529

233.2270

CI3H3N30Z

233.0226

234

CI3HzIN4
C I3 HsNp

233.1768

CIOHzzNz04 234.1580
CIOHz4N303 234.1819

CI4HI703
C I4 H04

233.1178

233.0464
232.9874

CIOH26N40Z 234.2057
C II Hz4N04 234.1706

Cl4HI9NOz
C I4 H3N03

233.1416
233.0113

CIIHz6Nz03 234.1945
C II H ION z0 4 234.0641

CI4H21N20
CI4HsN202

233.1655
233.0351

CIIHI2N303 234.0879
CIIHI4N40Z 234.1118

CI4Hz3N3
C I4 H7N3O

233.1894

CI2Hz604

234.1832

233.0590

CizHIZN04

C I4 H9N4

233.0829

C1sHzpz
C is Hs0 3

233.1542
233.0238

CI4H24N3
C I4 HsNp
C I4H ION 4

234.0542
233.9953

234.0668
234.0907
234.1620

C1sHzzOz
C 1s H60 3
C 1S HZ4NO

234.1859

C1sHsNO z

234.0555

CIsH26N2
C1SHIONzO

234.2098

234.0317

234.0794
234.1032

234.0766

CisHIZN3
C I6 Hz6 O
C I6H IOOZ

234.0681

ClzHI4Nz03

234.1005

C I6 HzsN

234.2223

ClzHI6N30Z
C I2N30 3

234.1244

C I6 H 1Z NO

234.0919

233.9940

CI6HI4Nz
C I6N3

234.0093

234.1985

234.1158

C 1S HZ3 NO

233.1781

CilHISN40

234.1482

C 1S H7NO z

233.0477

ClzH1N40Z

234.0178

C I7H30

234.2349

ClsHzsNz
C 1SH 9N P

233.2019

CI3HI404

234.0892

C I7 H I4O

234.1045

233.0715

233.9827

C I7 H I6N
C I7NO

234.1284

233.0954

CI3HI6N03
C I3 N0 4

234.1131

C is H II N3
C I6 Hzs O

233.1906

C I6 H9OZ
C I6 Hz7N

C I7 HzN z

233.0603

CI3HISNZOl 234.1369
C 13 H1N Z0 3 234.0065

233.9980
234.0218

C1sH 1S

234.1409

233.2145

C 13 HZON 3O

C1sHP

234.0106

234.1608

215

Mass Spectrometry

FM

FM

FM

C 1s H4N

234.0344

Cl4HIIN4

235.0985

Cl2H2N303

236.0096

C l9 H6

234.0470

ClsH2302
C 1s H70 3

235.1699

Cl2H20N40

236.1639

235.0395

236.0335

ClOH23N204 235.1659
C 1oH2SNP3 235.1897
C ll H2SN0 4 235.1784

C 1s H2SNO

235.1937

Cl2H4N402
C 13 H I6 0 4

C 1s H9N0 2

235.0634

ClsH27N2

235.2176

C ll H ll N 20 4 235.0719

CisHIIN20

235.0872

235

CIIH13N303

235.0958

CllHlSN402
C I2 H I3 N0 4

235.1196

ClsHl3N3
C l6H 27 O

235.2063

235.0845

C l6H l1 0 2

235.0759

C l6 H29N

235.2301

C l6H l3NO

235.0998
235.1236

Cl2HlSN203 235.1083
Cl2Hl7N302 235.1322

235.1111

Cl3HlSN03
C 13 H2N04

236.1049
236.1287
235.9983

CI3H20N202 236.1526
Cl3H4N203 236.0222
Cl3H22N30
C 13 H6N30 2

236.1764

Cl3H24N4
C13 HSN 40

236.2003

Cl4H2003
C l4 H40 4

236.1413

236.0460
236.0699

C l2 HN 30 3

235.0018

Cl2Hl9N40

235.1560

Cl6HlSN2
C l6HN 3

Cl2H3N402
C 13 H 1S0 4

235.0257

C l7 H31

235.2427

C l7 H 1SO

235.1123

Cl4H22N02
C l4 H6N0 3

236.1651

235.0970

Cl3Hl7N03
C 13 HN04

235.1209

C l7 Hl7N

235.1362

Cl4H24N20

236.1890

234.9905

C l7 HNO

235.0058

Cl4HsN202

236.0586

235.1447

C l7H 3N 2
C 1sH l9

235.0297

Cl4H26N3

236.2129

235.1488

Cl4HION30

236.0825

Cl4Hl2N4

236.1063

235.0422

235.1925

C1sHP
C1sHsN
Cl9 H7

235.0184

236.1777
236.0473

C I3 H7N 4O

235.0621

236

ClsH2402
C is Hs0 3
C 1s H26NO

236.2015

Cl4Hl903
C l4 H30 4

235.1334

CloH24N204 236.1737
CIIHl2N204 236.0797

C is H lON0 2

236.0712

235.0031

ClsH2SN2

236.2254

CllHl4N303 236.1036
CllHl6N402 236.1275

ClsHl2N20

236.0950

ClsHl4N3
C 1s N4

236.1189
236.0124

C l6 H2S O

236.2141

Cl6Hl202
C l6 H30N

236.0837

Cl3Hl9N202
C 13 H3N 20 3
C13 H21NP
Cl3HsN302
C13 H23 N4

Cl4H21N02
C l4 HsN03

235.0144
235.1686
235.0382

235.1573
235.0269

Cl4H23N202 235.1811
Cl4H7N202 235.0508
Cl4H2SN3
CI4H9N~O

Cl2Hl4N04

235.0171

235.0548

236.0923

235.2050

ClzHl6N203 236.1162
C 12N 20 4
235.9858

235.0746

ClzHlSN302 236.1400

236.0109
236.0348

236.2380

Spectroscopic Data Chemistry

216

FM
C I6 H I4 NO

236.1076

CI6HI6Nz
C I6NP
C I6 HzN 3

236.1315
236.0249

C I7 H3Z

236.2505

C I7 H I6O

236.0011

FM

FM

CI3HzsN4
C13 H9N4O

237.2081

C1sH z1

237.1644

237.0777

CI4HzI03
C I4 Hs04

ClsHsO
C 1SH7N

237.0340

237.1491
237.0187

C I9 H9

237.0705

237.0579

237.1730

238

236.1202

CI4Hz3NOz
C I4 H7N0 3

237.0426

C1Pz
C I7 H1SN

235.9898

CI4HzsNzO

237.1968

C 11 H I4NP4 238.0954
C II H I6N 3O, 238.1193

236. t440

CI4H9NzOz

237.0664

C I7 HzNO
C I7H4N z

236.0136
236.0375

Cl4H27N3
C I4 H II N3O

237.2207
237.09Q3

C11H1SNPz 238.1431
ClzHI6N04 238.1080
ClzHlSNz03 238.1318

C1gH ZO
C 1g H4O

236.1566

CI4HI3N4

237.1142

ClzHzNz04

236.0262

237.1855

C 1g H6N
C I9 Hg

236.0501

ClsHzsOz
C 1s H90 3

236.0626

C 1S HZ7NO

237.2094

ClzHzoN30Z 238.1557
CI2H4N303 238.0253
ClzH2ZN40 238.1795

237

C1SHIINO z

237.0790

CIIHI3Nz04 237.0876
CIIHISN303 237.1114

CISHZ9Nz
C 1S H 13 NZO

237.2332

CisHISN3
C 1S HN 4

237.1267
23.].0202

CIIHI7N40Z 237.1353
CizHISN04 237.1001

237.1029

C I6 Hz9O

237.2219

CI6HI30Z
C I6 H31 N
C I6H 1S NO

237.0916

CI6HI7Nz
C I6 HNP
C I6 H3N3

237.1393

C I7 H33
C I7 H I7 O

237.2584

CI3HzINzOz 237.1604
CI3HsNz03 237.0300

C I7 HO z

236.9976

C I7 H I9N

C 13 HZ3 N 3O

237.1842

C I7H 3NO

237.1519
237.0215

C 13 H7N,oz

237.0539

C l7 HsN z

237.0453

ClzHI7Nz03
C 1Z HNP4

237.1240

237.0552

236.9936

ClzHI9N30Z 237.1478
ClzH3N303 237.oI75
ClzHzIN40

237.1717

ClzHsN40Z
C 13 H I7 0 4

237.0413

CI3HI9N03
C I3 H3N04

237.1127
237.1365
237.0062

237.2458
237.1154
237.0089
237.0328
237.1280

238.0014

238.0491

Cl2H6N40Z
C 13 H 1S0 4

238.1205

C 13 HZON03
C I3 H4N04

238.1444
238.0140 .

CI3H2ZNzOz 238.1682
Cl3H6Nz03 238.0379
C13 HZ4N,o 238.1921
CI3HgN30Z 238.0617
CI3Hz6N4
C 13 H 1ON 4O
CI4H2Z03
C I4 H60 4
CI4Hz4N02
C I4 HgN0 3
C I4 Hz6NP
CI4HIONzOz
CI4HZgN3
C I4 H1Z N,o

238.2160
238.0856
238.1569
238.0266
238.1808
238.0504
238.2046
238.0743
238.2285
238.0981

217

Mass Spectrometry
FM

FM
CI4HI4N4

238.1220

CI5H2602
C'5 H JOO3

238.1934

C 1S H2SNO

238.2172

CI5HI2N02
C J5 H30N 2

238.0868

C I5 HI4NP

238.2411

CI2H5N303
C 12H23N 4O

238.1107
238.1346

C I6 H30 O

238.2298

CI6HI402
C I6 H32N

238.0994

CI6HISN2
C I6 H2NP
C I6 H4N3

238.0280

239.1072

239.0331
239.1873

C J6HJ7NO

239.1311

C 12 H,N40 2

239.0570

C I6 HN02

239.0007

CJ3H I90 4

239.1284

CI3H21N03
C I3 H5N04

C J6 H'9N 2
C I6 H3N P

239.1549

239.1522

C I6 H5N3
C I7 H35

239.0484

C I7H I9O

239.1436

239.1999
239.0695

C I7 H30 2

239.0133

C 17 H2I N

239.2238

239.1675
239.0371

239.0218

CJ3H23 N20 2 239.1761


CJ3H7N 20 3 239.0457

239.2615

239.0246
239.2740

239.0934

C I7H5NO
C I7 H7N 2

239.0610

239.1648

C 1s H23

239.1801

C1sH,o
C 1gH9N

239.0497

CI4H25N02
C I4 H9N0 3

239.0344
239.1886
239.0583

C I9 H II

239.2125

240

238.0167

C 17H20 2

238.0054
238.1597

CJgHgN
C J9 H JO

239.2376

C'6 H3JO
CI6HI502
C J6 H33N

239.1635

CI3H27N4
C 13 H II N4O
CI4H2303
C I4 H70 4

238.1358

C Jg H60

239.0359

237.9929
238.1471

C I7 H 1gO

C I7 H6N 2
C 1s H22

239.0120

C 13 H25N3O

238.0406
238.2662

C I7 H4NO

C I5 HNP
C'5 H3N 4

238.2536
238.1233

C I7 H34

C J7 H20N

239.1396
239.0093

238.0042

C I6N0 2

239.1158

C'2 H3N P4
CJ2H21N302

238.0630

CI5HI6N3
C I5NP
C I5 H2N 4

C I6 H I6NO

CI2HI7N04
C'2 H19N 203

FM

238.0293
238.0532
238.1722
238.0419
238.0657
238.0783

C13~N302

CI4H27N20

CJ4HIIN202 239.0821
239.2363
CI4H29N3
C I4 H 13N3O
CI4HI5N4
CJ5H2702
C J5 HI\03
C J5 H29NO

239.1060
239.1298

239.0736
239.0861

C'I H 16N 204 240.1111


CI\H 1gN30 3 240.1349
CI\H 20N 40 2 240.1588

239.0708

CJ2HJgN04 240.1236
C J2 H20NP3 240.1475
CJ2H4N204 240.0171

239.2012

239

C J5 H13 N02

239.2250
239.0947

CJ2H22N302 240.1713
CJ2H6N303 240.0410

CJIHI5N204 239.1032
C\lH I7N 30 3 239.1271
CJIHI9N402 239.1509

C J5 H3J N 2
C J5 H'5N 20

239.2489
239.1185

CJ2H24N40
CI2HgN402

C J5 HI7 N3

239.1424

CJ3H2004

240.1952
240.0648
240.1362

218

Spectroscopic Data Chemistry


FM

FM

FM

C 13 HZZ N0 3

240.1600

C l6 H 1gNO

240,1389

C l3 H6N04

240.0297

C I6HzNOz

240.0085

CI3Hz4NzOz 240.1839
CI3HgN203 240.0535

CI6H20N2
C I6 H4NP

240.1628

C l3 Hz7NP 241.2156
Ci3 H II NPz 241.0852
241.2394
CI3Hz9N4

240.0324

C I3 H 13 N4O

241.1091

CI3Hz6N30 240.2077
C 13 H IONPz 240.0774
240.2316
CI3H2gN4

C I6 H6N3
C l7H36

240.0563

CI4Hzs03
C I4 H90 4

241.1804

240.2819

C l7 Hzo O

240.1515

C 13 H 1ZN 4O

240.1012

C I7 H4OZ

240.0211

CI4Hz403
C I4 Hg04

240.l726

C I7HzzN

240.1753

240.0422

C l7 H6NO

240.0449

CI4Hz6NOz

240.1965

CI4HION03
Cl4HZgNZO

240.0661

C I7H gN 2
C 1g HZ4

240.0688
240.1879

C1gHgO
C1gHION

240.0575

C I9 H 1Z

240.2203

CI4HIZNzOz 240.0899
240.2442
C I4 H30N 3

CI4Hz7NOz
C I4 H II N0 3
CI4Hz9NzO

241.0501
241.2043
241.0739
241.2281

CI4H13NZOZ 241.0978
241.2520
CI4H31N3
CI4H1SN30

241.1216
241.1455

240.0814

CI4HI7N4
C l4 HN4O

240.0939

CIsHz90Z

241.2168

240.0000

CIsHI303
C 1s H31 NO

241.0865

CisH1SNOz

241.1103

ClsH33Nz
ClsHl7NzO
C1SHNZO Z

241.2646

ClsHl9N3
C 1s H3N 3O

241.1580

C 1s HsN4

241.0515

C l6 H33 O

241.2533
241.1229

CI4HI4N30

240.1138

C zo

CI4Hl6N4
C l4N 4O

240.1377

241

240.0073

C II H I7N/?4

241.1189

C1SHZgOZ

240.2090

CllHl9N303

241.1427

ClsH1Z03
C 1sH30NO
C1sH1,jNOz

240.0786

CllHzlN40Z

241.1666

240.2329

ClzHl9N04

241.1315

240.1015

241.1553

ClsH3ZNz

240.2567

ClzHzlNz03
ClzHsNz04

241.0249

241.0151

241.2407

241.1342
241.0038
241.0277

ClsHl6NzO

240.1264

C1sNzO z

239.9960

ClzHz3N30Z 241.1791
ClzH7N303 241.0488

C1SHlgN3
C 1s H2NP
C 1s H4N 4

240.1502

ClzHzsN40

241.2030

240.0198

ClzH9N402
C 13 HZ1 0 4

241.0726

Cl6Hl70Z
C l6 H0 3

241.1440

C l6 H3SN

241.2771

C l6 H3Z O

240.2454

241.1679

C l6 H l9NO

241.1467

Cl6Hl60Z
C l60 3
C I6 H34N

240.1151

Cl3Hz3N03
C 13 H7N04

241.0375

C l6 H3NO z

241.0164

C13HZSNZOz 241.1917
C 13 H9N 20 3 241.0614

Cl6HzlNz
C I6 HsNzO

24 l.l 706

240.0437

239.9847
240.2693

240.9925

241.0402

219

Mass Spectrometry

FM

FM

FM

C I6 H7N3

241.0641

CI4HIOO4

242.0579

C I7 HSNO

242.0606

C l7H21 O

241.1593

CI4H2SN02

242.2121

242.0845

C I7 HP2
C I7H23 N

241.0289

CI4HI2N03

242.0817

CI7HION2
C 1s H26

241.1832

CI4H30N20

242.2360

241.0528

CI4HI4N202

242.1056

C l7 H9N2
C 1sH2S

241.0767

CI4H32N3

242.2598

ClsHIOO
C 1S HI2N
C l9 H I4

242.0732

C I7 H7NO

241.1957

242.1295

C I9N

242.0031

C 1sH9O

241.0653

Cl4Hl6N30
C I4N30 2

241.9991

C 2oH2

242.0157

C lg H lI N

241.0892

243

C l9 H l3

241.1018

242.0229

ClIHI9N204

243.1345

C20 H

241.0078

CI4HISN4
C I4H2N4O
CIsH3002

242.1533
242.2247

ClIH21N303

243.1584

242.0943

ClIH23N402 243.1822
Cl2H21N04 243.1471

242
ClIHISN204 242.1267
ClIH20N303 242.1506

CIsHI403
C 1S H32NO

242.2485
242.1182

242.2036
242.0970
242.1096

CI2H23N203 243.1710
CI2H7N204 243.0406

ClsHI6N02
C 1sN0 3

241.9878

CIsH34N2

242.2724

C1sH1sNP

242.1420

Cl2H2SN302 243.1948
Cl2H9N303 243.0644

ClsH2N202

242.0116

CI2H27N40

CIsH20N3
C 1S H4NP
C 1s H6N4
C l6H34O

242.1659
242.0355

CI2HIIN402 243.0883
243.1597
CI3H2304

242.0594

C l3 HzsN03

242.2611

242.1757

Cl6H1S02
C l6 H20 3

242.1307
242.0003

C\3H9N04 243.0532
C\3H 27N 20 2 243.2074
C\3HI\N 20 3 243.0770

242.0453

C I6H20NO

242.1546

C\3H 29N 3O

Cl3H26N202 242.1996
CI3HION203 242.0692

C I6 H4N02

242.0242

CI6H22N2
C I6 H6N P

242.1784

C13H13N302 243.1009
243.2551
C\3H31 N 4
CI3HISN40 243.1247

CIIH22N402 242.1744
Cl2H20N04 242.1393
CI2H22N203 242.1631
Cl2H6Nz04 242.0328
Cl2H24N302 242.1870
Cl2HgN303 242.0566
Cl2H26N40

242.2108

CI2HION402 242.0805
242.1518
Cl3H2204
Cl3H24N03
C13 HgN 04

C I3 H2SNP

242.2234

242.0480

Cl3HI2N30Z 242.0930
242.2473
C I3 H30N4

C I6 HSN3
C I7 Hz2 O

242.0719

CI3HI4N40

242.1169

C I7 H6 0 2

242.0368

CI4H2603

242.1883

C I7 H24N

242.1910

242.1671

CI4H2703
C I4 H 1P4
CI4H29N02
C I4 H13N0 3

243.2187

243.1835

243.2312

243.1961
243.0657
243.2199
243.0896

220

Spectroscopic Data Chemistry

FM

FM

FM

CI4H31N20

243.2438

C I9 H I5

243.1174

CI4H2N302

244.0147

CI4HI5N202
C I4 H33N 3

243.1134

C I9 HN
C2oH3

243.0109

243.2677

243.0235

244.0386

CI4HI7N30
C I4 HN 30 2

243.1373

244

CI4H20N4
C I4 H4N 4O
CI5H3202

243.0069

CI4HI9N4
C I4 H3NP

CIIH20N204 244.1424
CIIH22N303 244.1662

CI5HI603
C I5 0 4

243.0308

CI5H3102

243.2325

CI5HI503
C I5 H33NO

243.2564

243.1611

243.1021

244.1690
244.2403
244.1100
243.9796
244.1338

CIIH24N402 244.1901
CI2H22N04 244.1549

CI5HISN02
C I5 H2N0 3

244.0034

CI2H24N203 244.1788
C I2 HSNz04 244.0484

CI5H20N20

244.1577

CI5H4N202

244.0273

CI5H22N3
C I5 H6N P

244.1815

CI5HI7N02
C I5 HN0 3

243.1260
242.9956

CI2H26N302 244.2026
CI2HION303 244.0723

CI5HI9N20

243.1498

CI2H2SN40

244.2265

C I5 HSN4

244.0750

CI5H3N202

243.0195

CI2HI2N402

244.0961

244.1464

CI5H21N3
C I5 H5N P

243.1737

CI3H2404

244.1675

CI6H2002
C I6 H40 3

244.0160

243.0433

C I6 H22NO

244.1702

243.0672

CI3H26N03
C 13 H ION04

244.1914

C I5 H7N 4

244.0610

C I6 H6N02

244.0399

CI6HI902
C I6 H30 3

243.1385

CI6H24N2
C I6 HsNzO

244.1941

243.0082

C13H2SN202 244.2152
C13HI2N203 244.0848

C I6 H21 NO

243.1624

CI3H30N30

244.2391

C I6H5N02

243.0320

244.1087

CI6H23N2
C I6 H7NzO
C I6 H9N 3

243.1863

C13HI4N302
C13 H32N4

243.0559

C 13 H I6N4O

244.1325

C I7Hs02
C I7 H26N

244.2067

243.0798

C 13N 40 2

244.0022

C I7 H IONO

244.0763

C 17 H23 O

243.1750

CI4H2S03

244.2039

244.1001

C I7 H70 2

243.0446

C14HI204

244.0735

CI7H12N2
C 1sH2S

C I7 H25 N

243.1988

CI4H30N02

244.2278

C 1s H 12 O

244.0888

C 17 H9NO

243.0684

C14HI4N03

244.0974

C 1SHI4N

244.1127

C I7 H IIN 2

243.0923

CI4H32N20

244.2516

C 1s H27
C1sH11O
C 1SH I3 N

243.0810

CI4HI6N202 244.1213
C I4 N20 3
243.9909

C1sN z
C I9 H I6
C I9 0

244.0062

243.2114
243.1049

CI4HISN30

C I9 H2N

244.0187

244.2629

244.1451

CI6HION3
C I7 H24O

244.0511

244.0637
244.0876
244.1828
244.0524

244.2192

244.1253
243.9949

221

Mass Spectrometry

FM

FM

FM
C 1s H04

244.9874

CI2H24N04

C\lH 2I N 20 4 245.1502
C\lH23 N30 3 245.1741

CIsHI9N02
C 1s H3N0 3
C 1S H21 NP

245.1416

CI2H26N203 246.1945
CI2HtoN204 246.0641

C\lH2SN 40 2 245.1979
CI2H23N04 245.1628

CIsHsN202
C 1s Hz3 N 3

245.0351

CI2H2SN302 246.2183
/
C I2 H I2N:P3 246.0879

245.1894

CI2H30N40

246.2422

CI2H2SN203 245.1866
CI2~NP4 245.0653

C 1s H7N3O

245.0590

246.1118

C 1s H9N4

245.0829

CI2HI4N402
C\3H260 4

246.1832

C12H27N302 245.2105
C I2 H\lN30 3 245.0801
CI2H29N40 245.2343

CI6H2102
C I6 Hs0 3

245.1542

CI3H2SN03

246.2070

245.0238

CI3HI2N04

246.0766

C I6 H23NO

245.1781

C I2 H\3N 40 2 245.1040
245.1753
C\3HzP4

C I6H7N0 2

245.0477

CI6H2SN2
C I6H9N P

245.2019

CI3H30N202 246.2309
C\3H I4N 20 3 246.1005
CI3HI6N302 246.1244

245.0715

C 13 N30 3

245.9940

C I6H\lN 3
C I7 H2S O

245.0954

CI3HISN40

246.1482

245.1906

CI3H2N402

246.0178

CI4H3003

246.2196

C I7H27N

245.0603
245.2145

CI4HI404

C I7 H 11 NO

245.0841

CI7HI3N2
C 1s H29
CisNIP
C1SH1SN
C 1SHN2

245.1080
245.2270
245.0967
245.1205

CI4HI6N03
C I4N04

246.0892
246.1131

245.1331
245.0027

C 2o H4

244.0313

245

CI3H27N03
C I3 H\lN0 4

245.1992
245.0688

CI3H29N202 245.2230
C I3 H\3N 20 3 245.0927
CI3H31N30 245.2469
C\3H 1SN30 2 245.1165
CI3HI7N40 245.1404
C I3 HN 40 2

C I7 H90 2

CI4H2903
C 14H\304

245.0100
245.2117
245.0814

CI4H31N02

245.2356

CI4HISN03

245.1052
245.1291

C I9H I7

244.9987

C I9H3N
C 20HS

CI4HI7N202
C I4HN 20 3
CI4HI9N30
CI4H3N302
CI4H21N4
C I4HsN 4O
CIsHI703

245.1529
245.0226
245.1768
245.0464
245.1178

C I9HO

245.0113
245.1655

245.0140

245.0266
245.0391

246

C\lH 22N 20 4 246.1580


C\lH24N30 3 246.1819
C\lH26N40 2 246.2057

246.1706

245.9827
CI4HISN202 246.1369
CI4H2N203 246.0065
CI4H20N30 246.1608
CI4H4N302 246.0304
246.1846
CI4H22N4
C I4 H6N 4O
246.0542
CIsHIS03
C 1s H20 4

246.1256

CIsH20N02
C 1s H4N03

246.1495
246.0191
246.1733
246.0429

CIsH22N20
CIsH6N202

245.9953

Spectroscopic Data Chemistry

222

Cl5Hz4N3
C l5 HgNp
C'5 H ION4

246.1972

C'6 HZZ02
C'6 H603
C'6 HZ4NO
C'6 HgNOZ

246.1620

246.0668
246.0907
246.0317
246.1859

FM

FM

FM

ClzHz9N30Z
C 1zH'3 N303
C'ZH'5 N40Z
C I3 H27 0 4
C I3 H29N0 3
C'3 H '3N04
C 13 H'5 N203
C'3 H'7N302
C l3 HN30 3

247.2261

C l6 H9NOz

247.0634

247.0958

C'6 HZ7N2
C'6 H ll N ZO
C'6 H I3 N,

247.2176

247.\196
247.1910
247.2148
247.0845

C'7H270
C'7H llOZ

247.0872
247.llll
247.2063
247.0759
247.2301

247.2427
247.1123

247.1560

246.1985

Cl3H19N40
C'3 H3N402

C'7H29N
C I7H 13 NO
C'7 H'5N2
C l7 HN3

247.0257

C 1gH31

C'7H IOO2
C'7 H28N

246.0681
246.2223

Cl4Hl504
C'4H I7N03

247.0970
247.1209

C 1gH l5 O
C I8 H'7N

247.1362

C l7 H l2NO

246.0919
246.1158

C l4 HN04

246.9905
C 14H'9N202 247.1447
C'4 H3N203 247.0144
Cl4H21N30 247.1686
Cl4H5N302 247.0382
247.1925
Cl4H23N4

C l8 HNO
C l8 H3N2

247.0058
247.0297

C l9 H l9

247.1488
247.0184
247.0422
247.0548

Cl6H26N2
C l6H lON2O
C16Hl2N3
C'7 H260

246.0555
246.2098
246.0794
246.1032

Cl7Hl4N2
C l7N3
C l8 H30
C l8 H l4O
C l8 H l6N
C l8NO

246.0093
246.2349
246.1045
246.1284

C l8 H2N2

246.0218

C l9 H l8

246.1409
246.0106

C l9 HP
C l9H4N
C2oH6
247

245.9980

246.0344
246.0470

247.1083
247.1322
247.0018

C l9 H3O
C l9 H5N
C2oH7

247.0998
247.1236
247.0171

C'4 H7N40
Cl5Hl903
C l5 H30 4
C'5 H21 N02

247.0621

248

247.1334
247.0031
247.1573

CllH24N204 248.1737
CllH26N303 248.1976
Cl,H28N402 248.2214

C'5 HSN 03
C'5 H23N P

247.0269

Cl2H26N04

247.1811

Cl5H7N202

247.0508
247.2050

247.1699

Cl2H28N203 248.2101
C 12H'2N 204 248.0797
C 12H'4N303 248.1036
ClzHI6N40Z 248.1275
248.1988
Cl3H2804
C'3 H I4N04 248.0923

247.0395
247.1937

C'3 H'6N203
C l3Nz0 4

CllHz3N204 247.1659
CllH25N303 247.1897
C ll H27N4OZ 247.2136
ClzH25N04 247.1784

Cl5Hz5N3
C l5 H9N3O
C'5 H II N4
C'6 H2302

C,zH Z7N z0 3 247.2023


Cl2HllNz04 247.0719

C l6HP3
C l6Hz5NO

247.0746
247.0985

248.1863

248.1162
247.9858

223

Mass Spectrometry

C I3 H,sN 3OZ 248.1400


C I3 H2N30 3 248.0096
C 13 H20N4O 248.1639

C'7 H30N
C'7 H'4NO
C'7 H'6N2

248.2380

C 13 H4N40 2
C'4 H1604

248.0335

248.0011

C I4 H,sN03
C I4 H2N04
C'4 H20N20Z
C'4H4N203
C'4 H2ZN30

248.1287

CI4H6N302
Cl4Hz4N4
C'4 HSNP

248.0460

C'7NP
C'7 H2N3
C 1sH32
C 1sH'60
C,sOz
C,sH,sN
C,sHzNO
C,gH4N2
C I9Hzo

CIsH2003
C,sH40 4

248.1413

CISH22NOz
C,sH6N0 3
C,sH Z4NzO
C,sHsNzOz

248.0586

CIsH26N3
C,sH ION3O

248.2129

C,sH,zN4
CI6Hz40Z
C'6Hg03
C'6 HZ6NO
C I6 H ION02
C'6 H2SN Z
C'6 H '2N ZO
C'6H '4N3
C'6N4
C'7 HZSO
C'7 H '202

248.1063

248.1049
247.9983
248.1526
248.0222
248.1764
248.2003

248.1076
248.1315
248.0249
248.2505
248.1202
247.9898
248.1440
248.0136
248.0375
248.1566

C I9HP
C'9 H6N

248.0262

248.0109

CZOHg

248.0626

248.1651

249-

248.0348

CIIHzsNz04 249.1815
CIIHz7N303 249.2054
C,zH Z7N04 249.1941

248.0699

248.1890

248.0825
248.1777
248.0473
248.2015
248.0712
248.2254
248.0950
248.1189
248.0124
248.2141
248.0837

FM

FM

FM

C'ZH\3N Z0 4
C'2 H ,sN 30 3
C'ZH I7N4OZ
C\3H1SN04
C'3 H'7N Z03

248.0501

249.0876
249.1114
249.1353
249.1001
249.1240

C\3HN Z0 4 248.9936
C'3 H '9N 30Z 249.1478
C 13 H3N30 3 249.0175
C\3H Z,N4O
C13 HSN402
C'4 H '704
C I4 H,9N03
C'4 H3N04

249.1717
249.0413
249.1127
249.1365
249.0062

C'4 H Z,N zO z 249.1604


C'4 HSN203 249.0300
C'4 H23N30 249.1842
C'4 H7N302
C'4 HZSN4

249.0539

C'4 H9N40
C,sH2,03
C is Hs04

249.0777

ClsH23N02
C,sH 7N0 3
C,sH2S N2O
C,sH9N 2OZ

249.1730

CIsHz7N3
C,sH II N3O
C'SH'3 N4
C'6 HZSOZ
C'6 H903
C'6 HZ7 NO
C'6 H IINOZ
C'6 HZ9N2
C'6 H I3N ZO
C'6 H ,sN3
C'6 HN 4
C'7 HZ90
C'7 H'30Z
C'7 H3I N
C'7 H ,sNO

249.2200

249.2081
249.1491
249.0187
249.0426
249.1968
249.0664
249.0903
249.1142
249.1855
249.0552
249.2094
249.0790
249.2332
249.1029
249.1267
249.0202
249.2219
249.0916
249.2458
249.1154

CI7Hl7Nz
C'7 HN ZO
C 17 H3N3

249.1393

C'SH 33
C'SH'70

249.2584

249.0089
249.0328
249.1290

224

Spectroscopic Data Chemistry


FM

C 1SH I9N

248.9976
249.1519

C 1S H3NO

249.0215

C 1s HsN2
C 19H21

249.0453

C I9 HP
CI9 H7N

249.0340

C 1s H0 2

C 2oH9
250

249.1644
249.0579
249.0705

CIlH26N204 250.1894
C12HI4N204 250.0954
CI2HI6N303 250.1193
Cl2HISN402 250.1431

250.1080
C13HI8N203 250.1318
CI3H2N204 250.0014
CI3H20N302 250.1557
CI3H4N303 250.0253
C 13H 22N 4O 250.1795
C 13 H6N 40 2 250.0491
250.1205
CI4HIS04
CI3HI6N04

C14H20N03
C I4 H4N04

250.1444
250.0140

CI4H22N202 250.1682
CI4H6N203 250.0379
CI4H24N30

250.1921

CI4HsN302

CIsH2203
C 1s H60 4

250.0617
250.2160
250.0856
250.1569
250.0266

CIsH24N02

250.1808

CI4H26N4
CI4HION40

FM

250.0504
250.2046
ClsHION20~ 250.0743
2502285
CIsH2SN3
CIsHI2N30 250.0981
250.1220
CIsHI4N4
256.1934
CI6H2602
250.0630
CI6HIOO3
C I6 H2S NO
2502172
CI6HI2N02 250.0868
2502411
C I6H30N 2
CI6HI4N20 250.1107
250.1346
CI6HI6N3
250.0042
C 16N,G
C I6 H2N4
250.0280
C I7 H30O
250.2298
250.0994
CI7HI402
H
N
250.2536
C I7 32
250.1233
C I7 H I6NO
249.9929
C I7N0 2
250.1471
CI7H1SN2
250.0167
C I7H2NP
250.0406
C I7 H4N3
C 1s H34
250.2662
C 1s H I8 O
250.1358
C 1sH20 2
250.0054
C 1S H20N
250.1597
250.0293
C I8 H4NO
250.0532
C 1s H6N 2
250.1722
C I9 H22
C I9 H6O
250.0419
250.0657
C I9 HSN
250.0783
C 2o H 1O
C1SHgNO)
C 1S H26N]O

FM

225

Mass Spectrometry

(a) If only C, H, N, 0, F, P, I are present, the approximate expected % (M + I)


and % (M + 2) intensities can be calculated by use of the following formulas:
%(M + I)
:: 1.1

100[(M+l)]
(M)

number ofC atoms + 0.36

% (M +2) = 100

number ofN atoms.

[(~~2) J

_ (1.1 x number ofC atoms) 2


200
+ 0.20 x number of atoms.

Table 5.4
COMMON FRAGMENT IONS

All fragments listed bear + 1 charges. To be used in conjunction with Table


5.5. Not all members of homologous and isomeric series are given. The list is
meant to be suggestive rather than exhaustive. Structural inferences are listed
in parentheses.
m/z

(Structural Inference)

Ions*

14
IS
16
17
18
19
26
27
28
29
30
31
32
33

CH2
CH3
0
OH
~O,NH4

F,HP
C=N, C2H2
C2H3
C2H4, CO, N2 (air), CH=NH
C2Hs' CHO
CH2NH2(RCH2NH2), NO
CHPH(RC~OH), OCH 3
2(air)
SH,CHl

226
34

Spectroscopic Data Chemistry

36

HzS
CI 7CI at 37)
HCI (H37CI at 38)

39

C3H3

40

CHF = N, Ar (air)
C3Hs' CHF = N + Ha, C 2H2NH

35

41

42
43

C3H6 , CzHp
C3H7, CH3C = 0, CH3C = OG, (G = R, Ar, NHz, OR, OH), CzHsN
H

44

CHzC = + H (Aldehydes, McLafferty Rearrangement),


CH3CHNH2, CO2, NHF = (RC = ONHz), (CH3)2N

CK
I ~
45

gHOH, CHzCHpH, CHPCH3 (RCHPCH3),

II

49

C-OH,CH3CH-O+H(CH3CHOHR)
N02
CHzSH (RCH2SH), CH3S
CH3S+H
CHFI(CHz 37CI at 51)

46
47
48

51

CHFz' C4H3

53

C4 HS

54
55

CH 2CHF=N
C4 H7, CHz=CHC=O

56

C4 HS

57

C4 H9 , CzHsC =

58

CH3-C, + H, C2HsCHNHz' (CH3)2NCH2' CzHsNHCHz, CZH2S


CH 2

59

(CH3)2COH, CHPC2Hs' C-OCH3 (RC02CH3)


NHzC =0+ H,

,/0

II

CHz
CHPCHCH3, CH3CHCHPH, CzHsCHOH

227

Mass Spectrometry

~O
60

CH 2C", +H, CHPNO


OH

o
61

65

66

II

CH3C-O + 2H, CH 2CH 2SH, CH 2SCH3

o
CsHs

=C,H"H,S, (RSSR)

67

CSH7

68

CH2CH 2CH 2C=N

69

C SH9 , CF3, CH 3CH=CHC=O,


CH 2=C(CH3)C=O

70

CSHIO

71

CSHll' C 3HF=O

72

ijO
C 2H sC" + H, C3H7CHNH2, (CH 3)2 N=C=O,
CH2
C 2HsNHCHCH 3 and isomers

73

Homologs of 59, (CH 3)3 Si

II
74

CH 2-C-OCH3 + H

o
II

II

75

C-OCzH s + 2H, C2HsCO + 2H, CH 2 SC 2H s' (CH3)2CSH, (CHP)2


CH, (CH3)2SiOH

76

C6HiC6HSX, C 6H4XY)

77

C6HS (C6HSX)

78

C6HS + H

79

C6HS + 2H, Sr (81 Br at 81)

228

Spectroscopic Data Chemistry

Q - C H2,

80
CRSS
, + H, HBr (H SIBr at 82)

I
H

81

eLH,.

C.H,.

82

CHFH 2CH2CHF=N, CCliC 3sCI37CI at 84, C 37Clz at 86), C 6H IO

83

C 6HII' CHCI 2 (CH3SCI 37CI at 85, CH37CI 2 at 87),

85

86

II
87

C3H 7CO, homologs of73, CH2CH2COCH3

II

88

II

CH2-C-OC 2Hs + H

lIJ-

229

Mass Spectrometry

91

lfH2(C6HSCH2Br)'lfH + H, ~ + 2H,

(CH 2)4 Cl[(CH 2)4 37Cl at 93]

92

93

([)c
I /.

H2,

g-CH,

+ H,

CH2Br(CH2 slBr at 95, RCH 2Br), C 7H9 ,

lJ=c=o,rQr- C,H,(t..-penes)
94

0-0
I /.

+H,

~~o
H

95

o-c~o

96

CH2CH2CH2CH2CH2CEN

97

C,H",

98

o-CH,O+H

99

C,H", C,H"O,

100

C 4 H9 C -..

0-

CH,

00

~O
:/'"

+ H, C SH Il CHNH2
CH 2

230

Spectroscopic Data Chemistry

o
101

II

C-OC 4 H 9

o
102

II
CH 2 C-OC3H7 + H

o
103

II

C-OC 4 H 9 +2H,C 5 H lI S,CH(OCH 2 CH 3 h

104

C2H5CHON0 2

105

JC=O
[C 6H5(C = O)G, G = OH, OR, OAr, halogen, NH 2],

~H,CH" ~HCH,
106

107

c&H'

~H,o,~
OH
C2H4Br(C2H4 sIBr at 109)

108

109

-CHP+H

c6fOH

231

Mass Spectrometry

III

O-C=O
S

CH 3

CH 3 CH

C= 0

- C-CH,. -CH,.-CH
I

120

C=O

121

t-

OH

o
122

II

C6HS C-O+ H,(C 6 H sC0 2 R)

123
125

127
128

HI

232

Spectroscopic Data Chemistry

130

o
.

II

131

C3FS' -CH=CH-C

135

(CHZ)4Br[(CHz)4 SIBr at 137]

138

C=O

139

141
147

6-

C1

CH2 I (RCHzI)
(CH 3)zSi = 0 - Si (CH 3)3

o
II

149

:~)+H
II

o
154

Ions indicated as a fragments + nH(n = 1,2,3---) are ions that arise via
rearrangement involving hydrogen transfer.

233

Mass Spectrometry
Table 5.5
Common Fragments Lost

This list is suggestive rather than comprehensive. It should be used in


conjunction with Table 5.4. All of these fragments are lost as neutral species.
Molecular
Ion Minus Fragment Lost

Inference Structure

2H

15

CH 3

16

O(ArN0 2, amine oxides, sulfoxides); NH2 (carboxamides,


sulfonamides)

17

HO

18

Hp (alcohols, aldehydes, ketones)

19

20

HF

26

CH=CH:CH=N

27

CH 2= CH", HC=N (aromatic nitrites, nitrogen heterocycles)

28

CH 2 = CH 2, CO, (quinones) (HCN + H)

29
30

CH3CH2, (ethyl ketones, ArCH 2CH 2CH3), CHO


NH 2CH 2, CHP(ArOCH3), NO(ArN02), C 2H6

31

OCH3(methyl esters), CHpH, CH3NH2

32

CHPH,S

33

HS (thiols), (CH3 and H20)

34

H2S (thiols)

35

CI

36

HCI,2H20

37

H2CI (or HCI + H)

38

C3 H2, C2N,

39

C3H3, HC 2N

40

CH 3C=CH

41

CH 2=CHCH 2

F2

234

Spectroscopic Data Chemistry

H)

C-

/"-.

42

CH 2=CHCH 3, CH 2=C=0, H 2G-CH?, NCO, NCNH 2

43

C3H 7' (propyl ketones, ArCH2---C3H 7), CH 3---C (methyl ketones, CH3CG,

II
where G

various functional groups), CH 2=CH-O', (CH 3' and

CH 2=CH2), HCNO

44
45

CH2=CHOH, CO 2 (esters, anhydrides), NP, CONH 2, NHCH2CH 3


CH 3CHOH, CH 3CHP' (ethyl esters), C0 2H, CH 3CH 2NH 2

47

(HP and CH 2=CH 2), CH 3CHPH, 'N0 2 (ArN0 2)


CH 3S'

48

CH3SH, SO(sulfoxides), 03

49
51

'CHFI

52

C 4H4, C 2N 2

53

C4HS

54

CH 2=CH-CH=CH 2

55

CH 2=CHCHCH 3

56

CH 2=CHCH 2CH 3, CH 3CH=CHCH3 , 2CO

57

C 4H9' (butyl ketones), C 2H sCO (ethyl ketones, EtC = OG,


G = various structural units)

58

'NCS, (NO + CO), CH 3COCH 3, C4H IO

46

59

'CHF2

II

II

CHPC", CH 3-C-NH2'
60

II

C 3 HPH, CH 2=C(OH)2 (acetate esters)"

H
61

62

(H 2S and CH 2=CH 2)

63

CH 2CH 2Cl

sI

235

Mass Spectrometry

CH 3

68

CH 2=C-CH=CH 2

69

CF3"' CSH9"

71

CsH\I"

o
II
73

CH3CHPC"

74

C4H9 0H

75
76
77

C6H3
C6H4, CS 2
C6Hs' CS 2H

78

C6H6, CS 2H 2, CSH4N

79

Br", CsHsN

80

HBr

85

"CCIF2

100

CF 2=CF 2

119

CF3-CF 2"

122

C6 HsCOOH

127

I"

128

HI

"Mclafferty Rearrangement

Problems:
(I)

List the possible formulas of molecules with M+ = 100. Assume


that C, Hand 0 may be present.

Strategy: A good approach to this kind of problem is to begin by


calculating the possible hydrocarbon formulas. First divide the molecular weight
by 12 to find the maximum number of carbons possible. Each carbon is equal
in mass to 12 hydrogens, so the next step is to replace 1 C by 12H, giving
another possible formula.

236

Spectroscopic Data Chemistry


Oxygen contain:ing fonnu[as can be calcu[ated by realising that one

oxygen is equal in mass to CH 4.

ADs.: Dividing M+ by [2 gives [00/[ 2 = 8 (remainder 4), so a possible


hydrocarbon forrmu[a is CSH4. Rep[acing [ C by [2H gives the second possible
hydrocarbon formula C 7H 16 .

Starting with the hydrocarbon fonnu[a CSH4 and replacing CH 4 by


gives Cp aSrPossib[e (but unlike[y) formula. Doing the same with C 7H l6 gives
C6HIP. Again rep [acing CH4 by

gives CSHS02' and repeating the process a

third time gives C4H40r Thus, there are five Iike[y formulas for a substance
with MW = 100.
(2)

Write as many molecular formulas as you can for compounds that


have the following molecular ions in their mass spectra. Assume
that all the compounds contain C 1 and H, and that mayor may

not be present.
(a) M+= 86,

ADS.

(b) M+ = 128,

(c) M+ = 156

(a) C6H 14, CSH100, C4 H60 2, C 3 H20 3


(b) C9H zo' C 9 HP, CIOHs' CSH I60, C7H 1P2' C6Hs0 3 CSHP4
(c) C 11 H24, C 12H 12, CllHsO, C IOH200, C IO H40 2, C 9H 160 2, CSH I20 3,
C 7H s04' C6H40 S

(3)

What are the masses of the charged fragments produced in the


following cleavage pathways?
(a) A[pha cleavage of2-pentanone (CH 3COCH 2CH 2CH 3)

ADS.

43,71
(b) Dehydration of cyc[ohexano[ (hydroxycyclohexane)

ADS.

82
(c) McLafferty rearrangement of 4-methy[-2-pentanone
[CH 3COCHFH(CH 3)2]

ADS.

58
(d) Aplha cleavage oftriethy[amine [(CH3CH2)3N]

ADS.

86

Mass Spectrometry

237

STRUCTURAL DATA OBTAINABLE FROM DIFFERENT SPECTRA

Characteristic and readily obtainable structural data from each type of


spectrum are collected below:
UV

Conjugation, substituents on Sp2 C atoms.

IR

Functional groups.

NMR

Carbon chain.

MS

Molecular formula, functional groups, carbon skeleton.

Details
UV

The following data can be obtained from a UV spectrum.

1.

The nature of conjugated system and substituents, from the


empirical rules for calculation of Amax of (a) polyenes, (b) enones
and (c) aromatic carbonyl compounds.

2.

The presence of aromatic units from the Amax 200 nm and Amax
260 nm (benzenoid) bands.

"

By comparing the shape of the spectrum of the unknown with

oJ.

spectra of known compounds it is possible to identify the nature


of the chromophoric units (cf. model compounds).

4.

Weakly absorbing chomophores (i.e., simple ketones, sulphides


etc., or n --+ cr' or n --+ 1t' transitions) are indicated by weak
bands in the absence of strong chromophores.

IR

The IR spectrum is extremely useful for the identitication of


functional groups in the unknown. 'The tables given in the chapter
on IR spectroscopy should be consulted. Briefly IR is helpful in
identifying the following:

1.

-OH; -COOH;

2.

-NH 2 ; -NH; -CONH 2; -CONH:

3.

C=C; HC=C; -CN; C=C=C;

4.

Aromatic rings, nature of substitution in the ring.

5.

Carbonyl functions.

6.

Enes and their cis-trans stereochemistry.

238
7.

Spectroscopic Data Chemistry


Alkyl units -CH(CH3)2; CH(CH 3)3
Note that absence of bands is also informative because if the
functional group is present it must give its IR bands. The
vibrations never stop.

NMR

The NMR spectrum gives valuable data about the carbon chain.

PMR

(Proton Magnetic Resonance) or lHNMR. The following


information can be obtained.

1.

The number of groups of equivalent protons and hence of the


nature of C atoms (5 values) in the chain (whether CH 3, CH 2
CH, etc.). The integration gives the number of protons in each
group of equivalent protons.

2.

The adjacent groups of protons (1, splitting patterns).

3.

Decoupling experiments identifY the neighbouring groups of


protons.

4.

NOE and J values indicate stereochemistry.

5.

Paramagnetic shift reagents simplifY complex spectra.

13C-NMR

The following information can be obtained:

I.

The number of equivalent groups of C atoms.

2.

The number of H atoms attached to each C atom (off-resonance


decoupling).

3.

Calculation of the chemical shifts of C atoms in the proposed


structure and comparison with the observed values, for
confirmation.

4.

Carbonyl functional groups.


The NMR spectrum is the most useful spectrum because it can
give almost the complete structure of the unknown compound
which may need only marginal information for confirmation.

MS

The mass spectrum provides data, some of which cannot be


obtained from other spectra.

1.

Accurate molecular weight and molecular fromula MtO. This


will be very valuable in those cases where only a small amount

239

Mass Spectrometry

of the unknown compound is available. Ion formulae can also


be obtained from high resolution MS.
2.

The class of compounds to which the unknown belongs can be


deduced from M + I abundance and the general appearance of
the spectrum.

3..

Functional groups from high m/z peaks and characteristic ion


series.

4.

Information about the C-skeleton from fragment peaks.

Reference Books used:


1.

Spectrometric Identification of Organic Compounds by Silverstein,


Bassler, Morrill, 5/e (John Wiley & Sons. Inc.).

2.

Absorption Spectroscopy ofOrganic Molecules by Y.M. Parikh (Addison


Wesley Publishing Company, California).

3.

Application ofAbsorption Spectroscopy ofOrganic Compounds by John


R. Dyer (Prentice Hall of India Private Limited, New Delhi, 1991).

4.

Organic Spectroscopy by V.R. Dani. (Tata McGraw - Hill Publishing


Company Limited, New Delhi, 1995).

ClClCl

Index

Abietic acid, 7
Absorption frequencies of:
alkenes, 45-46
aromatic homocyclic
compounds, 47-49
common organic compounds,

27-34
Alcohols: 13C chemical shifts,

111-12
Alkenes and alkynes: 13C
chemical shifts, 104-08
Amines: 13C chemical shifts, 114
Aromatic compounds:
13C chemical shifts, 108-11
Aromatic molecules:
carbonyl compounds, 13-20
dienes, 7-8
enones, 10-13
polyenes, 8-9
Aromatic systems and
derivatives: absorption
characteristics, 16-18
Auxochrome substituents, 6

Benzene chromophore, 5-6


Branched chain alkanes, 134
Calculating absorption maxima
of:
aromatic molecules, 5-13
carbonyl compounds, 3-5
unsaturated compounds, 1-3
Carbonyl compounds, 3-4
Carboxylic acids, ester,
chlorides, anhydreds, amides
and nitriles: 13C chemical
shits, 116-20
Chemical shifts, multiplicities and
coupling constants, 86-88
Chemical shifts:
alicyclic rings, 72
alkyne protons, 77
fused aromatic rings, 78
heteroaromatic rings, 79
heterocyclic rings, 72-73
methyl, methylene and
methane protons, 65-67

241

Index
miscellanceous alkenes,

75-77
monosubstituted benzene
rings proton, 77-78
substituent effects, 70-71
two/three functional groups,

68-70
unsaturated and aromatic
systems, 73-75
Chromophore substituents, 6
Common fragmentation ions,

225-32
Common fragmentation lost,

233-35
Coupling constants, 122
Cross conjugation, 1
Cutoff wavelength, 19-20
Cyclic diene, 1

Ethers, acetols and epoxides:


13C chemical shifts, 112-13
Exact masses of isotopes,

129-30
Fragmentation process:
alcohols, 137-40
aldehydes, 144-45
alkanes, 132-34
alkenes, 135-36
amides, 151-52
amines, 149-51
aromatic hydrocarbons,

136-37
carboxylic acids and esters,

147-49

Dicarbonyl compounds, 12
Diene absorption: Woodword's
and Fieser's rules, 2
Diens and triens: kinds of, 1-2
Different spectra: structural data
obtainable, 237-39
Effects of chemical shifts on:
alicyclic and heterocyclic
rings, 73-80
protons on heteroatoms,

ethens, 142-43
ketones, 145-47
phenols and other aromatic
alcohols, 140-42
Halides: 13C chemical shifts,

113-14
Heteroannular diene, 2
Heteroatoms, 80-81
Homoannular diene, 2
Incremental shits of aromatic
carbon atoms of
monosaturat.::d benzenes,

80-81

108-10

single functional groups,

Incremental substituents effects,

65-67
two/three functional groups,

68-71
Enone and dienone absorption
rules, 4-5
Enone: solvent correlations, 5
Ergosterol, 8

102
Infrared absorption and structure
of organic compounds:
correlations, 34-35
Ketones and aldehydes: 13C
chemical shifts, 115-16

242
Linear and branched alkanes:
13C chemical shifts, 94-104
Linear conjugation, 1
Mass spectroscopy, 128-235
Mass spectrum, 128
McLafferty rearrangements, 135,
136,144,147
Molecular ion, 128-29
Mulling oils, 58
Multiplicities, 13C chemical shifts
and couplings of common
NMR solvents, 123-24
NMR spectroscopy, 90-127
NMR table of correlations of
chemical shifts of protons,
88-93
Ortho and meta substitution,
15
Oximes: 13C chemical shifts,
120
Para substitution, 14
Parameters of 13C chemical
shifts, 100
Polycyclic aromatic compounds:
absorption characteristics, 15
Polyenes,3
Proton magnetic resonance
spectroscopy, 64-93
Proton spin coupling constants,
81-85
Protons on heteroatoms,
80-81

Index
Recognition of molecular ion
peak, 131-32
Relative isotopic abundance of
common elements, 130
Retro-Diels-Alder reaction, 135
Scott's rule for "-max of ET band,

6-7
Semicyclic diene, 1-2
Shielding constants, 68-69
Solvents and mulling oils: infrared
transmission characteristics,
57-58
Some CJ CH ) values, 120-21
Some eJCH) values, 121-22
Spin coupling, 120-22
Stretching frequencies of:
carbonyl compounds, 49-53
cyclic and acyclic systems, 47
Substituent constants, 74-75
Substituent effects on chemical
shifts, 70-71
Table of 13C correlation for
chemical classes, 124-27
Thiols, sulfides and disulfides:
13Cchemicalshifts, 114-15
Trans f3-carotene, 8-9
Translycopene, 9
Ultraviolet spectroscopy, 1-20
Variations of carbonyl stretching
band,53-54
Vibration modes of amines and
amino acids, 55-56

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