Professional Documents
Culture Documents
Spectroscopic Data
CHEMISTRY
(UV, JR, PMR, JJCNMR and Mass Spectroscopy)
B.D. Mistry
B.K.M. Science College.
Va/sad - (Gujarat)
ISBN: 978-81-89473-86-0
Edition 2009
Reserved
Typeset by:
Shivangi Computers
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. Mehra Offset Printers, Delhi.
All Rights are Reserved. No part of this publication may be reproduced. stored in a
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\HItten permission of the copyright owner. Responsibility for the facts stated.
opinions expressed, conclusions reached and plagiarism, if any, in this volume is
entirely that of the Author, according to whom the matter encompassed in this
book has been originally created/edited and resemblance with any such
publication may be incidental. The Publisher bears no responsibility for them,
whatsoever.
Contents
1.
Ultraviolet Spectroscopy
2. Infrared Spectroscopy
3. Proton Magnetic Resonance Spectroscopy
4. Be NMR Spectroscopy
5.
Mass Spectrometry
6.
Index
1
26
64
99
128
237
240
Ultraviolet Spectroscopy
1.1
iii)
iv)
o
o
v)
Table 1.1: Woodward's and Fieser's rules for Diene absorption (ethanol
solution)
i)
ii)
214 nm
253 nm
Increments for
iii) Extra double bonds in conjugation (for each C=C)
+30 nm
+5nm
Onm
+5nm
+5nm
d) O-alkyl (-OR)
+6nm
e) S-alkyl (-SR)
+30nm
+ 60 nm
Onm
Ultraviolet Spectroscopy
,
228 nm
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
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
>c=o (-one), as in
> C = C- C = 0
.
IS
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
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
Correction
o
o
-8 nm
+ I nm
+5 nm
+7nm
+ 11 nm
+ II run
~ 1t
-N~,
-OH,
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
214nm
05nm
Substituents R (4
20nm
5)
Calculated Amax
239nm
Observed
241 nm
8
(2) Ergosterol
HO
253 nm
lOnm
Substituents R (4 x 5)
20nm
Calculated "'-max
283 nm
Observed
282 nm
3.3, j3-Acetoxyergosta-5,7,14,22-tetraene
4
323 nm
319nm
Calculated "'-max
Observed
II. Polyenes
(1) All trans j3-carotene
Me
Me
Me
Me
Me
Ultraviolet Spectroscopy
114 nm
50 nm
11
[48-(1.7
11)]
add
322.3 nm
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
15.2 x 10 4 (observed*)
Emax
114 nm
Basic Amax
M=5 x 8
add
40nm
n= 11 x 148-(1.7 xII)
add
322.3 nm
max
= 1.74
substract
00.0 nm
substract
00.0 nm
Calculated Amax
476.30 nm
Observed
474.00 nm
x II x 104
= 18.6
x 104 (observed)
10
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
add
5nm
add
10nm
12)
add
12 nm
0(\ x 18)
add
18 nm
~ (\ x
Calculated A. EtOH
max
329 nm
Observed
327 nm
II
ot~H
IK. p
Parent base
Substituents a(l x lO)
add
IOnm
~(lxI2)
add
12 om
add
05 nm
195 nm
222 nm
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
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
274,
C.CH.
-'"
CH
Acetyl acetone
>CH.--C
CH 2
"'rna,,;
Ema~ 12,000
E
max
2050
-f"
'
Ultraviolet Spectroscopy
13
(Emax
22,000) in ethanol
O~OH
O~O
V<-->~ -V
1,3-Cyclohexanedione
(7t ~ 7t*
K-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
o
II
1.
I -. . . :
HO"'-.cr
/
HO
Base value
"-. CH
246nm
OHinm
07 nm
OH inp
25 nm
278 nrn
14
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
a.
b.
15
Ultraviolet Spectroscopy
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
16
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
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
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
295
25,000
Submerged
268
10,700
(trans)
272
15,900
biphenyl
Diphenyl-
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
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
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
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
19
Ultraviolet Spectroscopy
Emax
Q
HO
tropolone
azulene
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
290
1, I-Dichloroethane
235
Xylene
295
Dich loromethane
235
20
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
2.
= N~
~ NO
(CH.)
, 2N-~N
)=/
2
CH 3
"-max = 438, E = 22,000
....
.).
(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.
Biphenyl
K-Band, t..max ~ 252,
o-xylene
22
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)
GO
CO
co co
23
UltravIolet Spectroscopy
~ 7t*
18,600).
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;
24
(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.
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
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
Vibration
mode
1. Alkanes
-C H3
Frequency.
cm- I
2975-2950
-C(CH 3)3
C-Hdef.
Skeletal
-CH 2-
2880-2860
1470-1435
1385-1370
1385-1365
1175-1140
840-790
1395-1365
1255-1200
750-720
2940-2915
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
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.
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.
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.
3,70-4-00
w.
v,
b) Carboxylic acids
AIIOH
O-H def.
955-890
10 47-11.24
CH 2 vib.
1350-1180
740-8.48
w.
characteristic
pattern
-COOH
Carboxylate ion
1440-1395
6,94-7.17
w.
1320-1210
758-8.26
s,
s
m,
6.21-6.45
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
1300-1250
7.69-8.00
s.
C-O str.
1220-1200
8.20-8.33
s.
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
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.
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
NH
C-N str.
(amide II band)
1620-1590
(amide II band)
Secondary, free NH
bondedNH
3440-3420
3460-3430
2.89-2.92
s.
3180-3140
3.15-3.19
m.
3330-3270
3.00-3.06
m.
3100-3070
3.23-3.26
w.
Ca.700
Cal4.30
(amide V band)
N -H def. plus
C-N str.
Acyclic compound
1305-1200
conc.
dependent
7.67-8.33
m.
6.37-6.60
s.
6.45-6.62
s.
31
Infrarred Spectroscopy
770-620
1300-16.13
m.
15.87-18.87
s.
(amide IV band)
630-530
(amide VI band)
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
P unsat.
compounds
Cyclic a,
P unsat.
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
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
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.
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
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
1440-1350
6.94-7.41
S.
(RO)z S02
Covalent sylfonates
1230-1I50
8.13-8.70
S.
1420- 1330
7.04-752
S.
(R,-O-S02-R2)
Sulfonyl chlorides
1200-II45
8.33-8.73
S.
1375-1340
7.27-7.46
S.
(R-SOzCI)
Sylfonamides
I 190-II60
8.40-8.62
s.
1370-1300
7.30-7.69
S.
33
Inti-arred Spectroscopy
(R-S02-N)
1180-1140
8.48- 8.77
s.
Sulfones
1350-1300
7.41-7.69
v.. -so
(R2S0 2)
1160-1120
862-8.93
v., -so
Sylfonic acids
1260-1150
7.94-8.70
s.
(RS0 3 H)
1080-1010
9.26-9.90
s.
Sylfites (RO)2S0
S=O str.
1220-1170
8.20-8.55
s.
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.
P-OH
P-O-P
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 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
B-H str.
s.
34
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
d.=doublet
br.=broad absorption
mlt.=multiplet
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.
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.
O-H str.
3550-3205
2.82-3.12
w.
C=O str.
N-H str.
Carboxylic acids,
free OH
3540-3380
2.83-2.96
s., d.
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.
N-H str.
N-H str.
Nitrites (R-O-N=O)
overtones
N=O str.
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
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.
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.
O-H str.
3175-3135
3.15-3.19
m.
3150-3050
3.18-3.28
w.
N-H str.
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.
3095-3075
3.23-3.25
m.
Alkenes (CHR=CH z)
3085-3040
3.24-3.29
v.
N-H str.
RC-H str.
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
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.
36
3000-2001
2975-2950
3.36-3.39
m.
Alkanes (-CH J )
C-H str.
2940-2915
3.40-3.43
m.
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.
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.
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.
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=O str.
C=O str.
overtone
C-H str.
\840-1800
5.44-5.56
s.
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
C-H str.
1800-1770
5.56-5.65
s.
C=O str.
1800-1770
5.56-5.65
s.
C=O str.
1800--1760 5.56-5.68
s.
C=O str.
1795-1740
s.
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.
C=O str.
38
1780-1760
5.62-5.68
s.
C=O str.
1780-1740
5.62-5.75
s.
C=O str.
1760-1730
5.68-5.78
s.
Simple
Plactams
C=O str.
1760-1720
5.68-5.81
s.
C=O str.
1755-1740
5.70-5.75
s.
C=Ostr.
1755-1730
5.70-5.78
s.
C=O str.
1755-1720
5.70-5.81
s.
C=O str.
1750-1740
5.71-5.75
s.
Ketones. 5 ring
C=O str.
1750- 1735
5.71-5.76
s.
i750-1735
5.71-5.76
s.
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.
C=O str.
i740-1720
5.75-5-81
s.
C=O str.
1740-1715
5.75-5.83
s.
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.
C=O str.
1730-1715
5.78-5.83
s.
a,
1730-1700
5.78-5.88
s.
C=O str.
1725-1705
5.80-5.87
5.80-5.88
s.
C=O str.
1725-1700
s.
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.
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.
('=0 str.
1700-1665
5.88-6.01
('=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.
C=O str.
1690-1670
5.92-5.99
W.
5.92-5.99
s.
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.
C=O str.
same ring
oxazolones, azomethines,
acyclic C=N
C=N str.
ca. 1680
ca. 5.95
s.
C=O str.
1680-1660
5.95-6.02
s.
C=O str.
1680-1650
5.95-6-06
s.
Intramolecular H-bonded
carboxylic acids
C=O str.
N=O str.
1680-1650
5.95-6.06
v.
1680-1630
5.95-6-14
s.
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.
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..
C=N str.
40
ca. 1660
ca. 6.02
s.
c=o str
1660-1640
6.02-6. \0
v.
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.
1660-1480
6.02-6.76
v.
C=C str.
1655-1635
6.04-6.12
s.
C=N str.
C=O str.
1655-1635
6.04-6.12
s.
Quinones, 2 CO's in
1655-1610
6.04-6.21
s.
1655-16\0
6.04-6.21
s.
ca. 1650
ca. 6.06
s.
1650-1590
6.06-6.31
s.
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.
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.
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.
1625-1575
6.16-6.35
v.
Aromatic homocyclic
N=Ostr.
form)
compo
1620-1600
6.17-6.25
S.
Tropolo!)es
1620-1600
6.17-6.25
S.
C=O str.
I band
1620-1590
6.17-6.31
s.
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.
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.
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.
amide II band,
combination NH def.
and CN str.
NH def. + CN str
42
1570-1500
6.37-6.67
s.
N-H def.
C=C str.
ca. 1565
ca. 6.39
v.
Pyrroles
1565-1545
6.39-6.47
s.
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.
1550-1510
6.45-6.62
s.
1550-1485
6.45-6.73
v.
NH3+ def.
NH def. + eN str.
Amino acid
hydrochlorides
1545-1530
6.47-6.54
s.
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.
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.
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
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.
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.
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.
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.
s.
adjacent H atoms
C-H def.
Halides
C-Cl str.
atoms
770-730
12.98-13.70
V.,
s.
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
Alkene type
Frequency,
cm- I
RCH=CH z (Vinyl)
H
'R)C=C<H
Wave
Relative
length,11 intensity
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
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
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
1675-1665 5.97-6.01
840-790 11.90-12.66
v
m
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
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
Vibration
compound
mode
Frequency,
em-I
Monsubstituted
=C-H sir.
(Multiple bands)
3080-3030
3.24-3.33
(five adjacent
hydrogen atoms)
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
8.45-8.54
w
w
Wave-
Relative
length,l!
Intensity
1156 5(3,5 vs 4)
8.61-8.69
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
859-865
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 str.
(three adJacent
(multiple bands)
hydrogen atoms)
C=Cstr
(ring stretching)
1600~
1620
1586 5
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)
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
12.82-12.96
725
m
w-m
6.20-6.25
631-6.36
v
v
1:4 Disubstltuted
(two adjacent
hydrogen atoms)
1579 6
1520~ 1480
1409 8
658~6.76
7.05-715
7.88-802
w
w
8.90-9.01
9.82-9.92
12.02-12.47
3080-3030
1606 6
817 15
3080-3030
1175
1110
~
~
1125
1070
1070 ~ 1000
C-H o-o-p def.
1:2.4-Trisubstltuted
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
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~
Tetrasubstltuted
(multiple bands)
C-H lH>-p def
w
w
1l1l~1163
11.56 ~ 12.30
865
=C-H str.
730 ~ 675
1:2:3 :4-
8.51~889
10.00
1000
9.35
13 70
3080-3030
860 ~ 800
=C-H sIr.
1:2:3:4:5
(multiple bands)
3080-3030
900~
14.82
324-333
II 63
w-m
1250
3.24-3.33
w-m
substituted
860
ILl I
11.63
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.
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
b. Saturated, 5-
1870-1820
5.35-5.49
membered ring
1800-1750
5.56-5.71
Succinic anhydride(CHC1)
50
c. a,
p- Unsaturated
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
Butyric acid
(monomer) (CCI 4 )
Acetic acid (CCI 4 )
Butyric acid (Film)
a- chloropropionic acid (Film)
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
1748
5.72
1736
5.76
1733
5.77
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,
~-
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
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
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)
5.83 (sh.)
1680-1630
5.95-6.14
1700-1670
5.88-5.99
b. Secondary (RCONHR)
solid and concentrated
solution
dilute solution
at 1705
5.86 (sh.)
1670-1630
5.99-6.14
5.85 (sh.)
53
Infrarred Spectroscopy
d. Cyclic, o-Iactams, dilute solution
-1680
-5.95
-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
-1640
-6.10
-1720
-5.81
1740-1690
5.75-5.92
-1710
-5.85
-1700
-5.88
-1710
-5.85
~-Iactams,
dilute solution
h. Cyclic,
~-lactams,
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,
~-
-1700
-5.88
-1790
-5.59
-1710
-5.85
Shift to higher
frequency
Basic value in CCI4
1720
Shift to lower
frequency
Substract
cm- I
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
15
Bridged systems
Substitution on a-carbon
Substitution on'a-carbon
20
5
-NHMe (monosubstituted amide) 30
-NMe2 (disubstituted amide)
55
-NH2 (amide)
Weak: a or
~-OH
ketone
nonplanar
Strong : ~-diketone
-H (aldehyde)
-OR (ester)
-OH (monomeric acid)
-O-C=C (vinyl ester)
10
25
40
50
10
40
100
15
45
conjugation (depends
on stereochemistry)
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)
1340-1250 (aro)
(7.46-8.0f..l)
=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
(2.82-2.99f..l)
(6.06-6.45f..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
(7.24-7.94f..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
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
Acetone
Absorption
(em-I)
3480-3340,3180-2730,1890-1060,940-880,
805-790, 600-630
Acetonitrile
Benzene
3150-2960,2000-1935, 1860-1790,
1545,
1500,1445-1365,1190-1140,1070-980,865845, 600-750
Benzonitrile
Bromoform
Bromotrichloromethane
600-840
Butyl acetate
I-Butanol
3600-2500, 1600-600
Dibutyl ether
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
58
Solvent
Absorption
(em-I)
CycIopentane
1,2-Dichloroethane
Diethyl ether
1,4-Dioxane
3060-2650,2000-1965, 1460-1075,940-825,
690-600
Dodecane
3060-2650, 1460-1290,755-695,665-600
Hexane
Tetrachloro ethylene
1060-1035,960-885,830-745,680-600
1,1-Trichloro-trifluoroethane
2,2,4-Trimethylpentane
Water
Mulling Oils
Absorption
(em-I)
Nujol
Hexachlorobutadiene
1650-1500,1280-1200, 1020-760
Fluorolube
1350-650
Infrarred Spectroscopy
59
[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.
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
60
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
follows:
a. Benzophenone in chloroform
1720 em-I
-40 em-I
- 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
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
./'
CH 2
~
CH 2-CH 2--C=0
1720 cm- I
- 30 cm- I
-5 cm- I
-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
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
+ 50
Calculated
1770 em-I
ClCHJ
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
65
-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
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
Table 3.2: Chemical shifts of Methyl, Methylene and Methine protons (~to the functional groups) in 0
Functional group 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
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
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
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. ."."
~ ~ ~
uo
,....
f rf
u.
Ul
UO
2.17 U. 140
-6C
1,.
....
-'"
J.n
-cP.
).So
.-"
i"
2.11
I .. '
~ ? 0.I
,...,
1 ..
;:;
cso ....s
Ut U2 <AI '.1
-<:P,
. f ~
... .... u. ...,
. ,. 4."
"u
I
)"IS
Uf
u.
u.
)." I.,. 1M
,....
,ft ,,., u.
2.40 )
).lS
U, '.ft
...
......,,
UI
c.,.
'.It
uo
...
'ol'
...0 U1 '.$1
4.t1 S.OI 1.$'
UI S.1\ I."
'..,
.n
"~
p.u
l-
I~: uo
.. U
J.lO "w 12.
,...
1.lS
,,'.......22
"".
0
f
q q
1:1, U1
Ut
....'At
1JI
U7 2." 2.41
J.)'
1.12 Ul Ul 11f
I;:;
1f1
I.n
"'1
U. ...1
'At
'I'
,;:
2.1
'.0' iu
....
Lt.
.
"
....
,
...
'." ..... ....
....... ..., .... ..... ..os".11 ".Jf.." ... ......" "...."......
'.11
....
,
.., ,.ft ...,
-.. .
.,. 'TO ....
".J)
J.f)
U'
U1 J,n:
I."
1 ..
....$411.4)7 J.21
Ul
-Q
C.U 2.47
UI
I(
f g
,
~I 13
I
q If
',12
-,
'00
4.J. "11
s.Tt
SA.
J.11
5,
S."
..., '.4'
,Us
-<lIf~
...,.
ffg
".55
"OJ U,
....
SIl
-OPfo
U.
'.n
J.t2
....., ...".IJU
S ....
5.10
....
lA.
...." .....
..
'.20
.....
c... ".IS .... ...
c..,
.,U
5... J.J.
US 1.10
,.co
-CC-<)).
c...
4.U ".02
U,
J.oI
J.OI
.s. ."
L..
J.41
c..,
, ,... ""
U,
3M C" .. U
UJ
l.l .. J.1t ,.co
11S
Ul
-<10"",0.
I.OJ 11J
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
1"
....
..!!.!~
-..
70
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
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
I I
Pa
Substituent
-c=C-
Beta shift
0.78
0.75
0.10
71
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
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
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
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
R~
CIS
"""
/C=
R trans
Rgem
oH = 5.25 + ~zi
i.e. 5.25 + Zgem + Zcis + Ztrans
C6H~
/OC 2Hs
C
Ha /
-c:....
-
"'-Hb
are calculated
74
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
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
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.
RCH
650
502
= CR-CH = CH 2
6.01
608
716
CH 3 -CH = CH-CH
5.62
= CH-COOC 2 H5
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
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
1.73-1.88
2.23
1.95
1.80
2.71-3.37
2.60-3.10
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
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
7.39
7.88
7.82
8.12
79
'"
{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~
GO
I
9.92
"C~N, (al,.
RCH=O
PhCH=O
9.70
RCH=CHCH=O
9.78
9.98
"+0 )
o
Proton'
80
8.05
8.05
HCOOR
HCONR2
RCB=NOH cis
5.00
7.25
6.65
RCH~N-NH~NO,
6.05
HC(OR)3
N02
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
Class
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
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
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
II
>CH.-CHb
0
II
C=CHa-CHb
Ha)c=e<Hb
CHa
CHb
83
)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
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
5.5-7.0
1.5
Proton Fluorine
>C<H
Fb
44-81
85
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
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
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)
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
88
2,2,2-Trifluoroethyl
alcohol- d,,
3.88 (4
103.059
a
b
5.02(1)
x
3)
2(9)
'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.
8.5-8.9"
1.5-1.1
-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
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.
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.
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
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
-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.
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.
(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
3:5
HFf ')-cH3
3:2
94
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
10
J
7
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
(ustandard)
(u sample -
U TMS )
97
DzO. For aqueous solutions, the standard used is often the sodium salt of
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
/"7f-//I~::,j,
-- ''r\t:P
1/ , I
~ C;:=lO
/k.
~
~;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
/+ 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
=-2.5 + (9.1
1
I) + (9.4
I~-,
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]
+ (-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
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
+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
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
...
~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
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
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
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
CH3H
P a
H3 C-CH 2 5
0C_3
C = C -CH3
3
= 142.7 ppm.
a'
CH3H
W a'
H,C-CH 2 Os
0C_2 =
123.3 + (I
-<
C =C
3
-cI H3
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
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,
-
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.
.'
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
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 ~~"
II
I.' i"
o
1077
f-l,~rn"CN
1~7K
144 I
117~
o
A,133.8
L~165.1
CH
108
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
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
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
CH
0
+8.2
+1.2
+0.6
+5.8
192.0
CCH 3
0
+7.8
-0.4
-0.4
+2.8
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
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
+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 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
14.8
Substituent
13.4
178.2
159.1 (C=O),
51.8 (CH)
182.8
38.1
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.
H,C;~ /CI-~"'-
CHpH
CH 2
490
OH
25K
~5
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
]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
52"
H,C,
]jJ
..,.-/~
Cf~
~q
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
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)
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
)SA
/C~
79/,
H~C
.
~2111
'i
.,
.,
CH.,
~
" /
H 2 C, ---CH 2
i
CH 3
"'lox"
- -C - -- --- CH 2
/
~7X
116
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'.~"''''
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
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
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
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
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
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
J(HZ)
Sp3
C.!:i3~H3
C.!:i3~CI3
-4.5
5.9
122
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
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
123
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
CD 3CDPD
(CD 3CD2 )P
Ethanol-d 6
Ether-d 1o
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)
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
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,
36-54
197-220
176-194
195-220
13 unsat.
R-C=C-C=O
182-212
166-186
174-194
126
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
';(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
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
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
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
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
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,
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
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.
Straight chain alkanes show low intensity molecular ion peaks. The
intensities of these peaks decrease with increasing chain length.
133
Mass Spectrometry
""
. ..
100l~:tlon) CH 3CH; +CH 2CH 2CH 2CH 3
(Parent ion)
134
<
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
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
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)
+
(i)
>
[~r
II "
136
CH?
(ii)
II CH 2
An
a~omatic
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
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
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
Methanol
+
H +H 2 C = O-H
mle = 31
M-l
Ethanol
.;
R-C-O-H
)R-C
=O-H
(M-l)
.
+
) R-C =0
H
(M-2)
l-H"
R-C=O
(M-3)
139
Mass Spectrometry
(m-IS)
+Hp
OH
~H
l
H fromC 3
[0 r
-HP, H fiom C4
when cyclohexanol is
in the boat form
140
"'..;
~'-.CHR
HC
2
H,C,
/C"""
/
C-C
/ \
/\
HHHH
+/HR
-~
m=28
/C"""
H
+ Hp
M-46
1:
-He
(M-l)
very intense
(abundant)
R-CH=~~H---+R-CH=CH+CH2=OH
I
H
(less abundant)
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
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
142
,0
mle = 79
(M-29)
mle
77
(M-31)
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.
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.
H-f~H2
I
CH 3CH 2-C
~;
CH3
'\
H.
I
CH 2
/CH2~CH3CH2-C-OH+
,-
'/}
CH3
II
CH 2
(\ ;)-J-CH2CH3 _-O
_ _C_H-=.2_CH---=-34)
eliminate an alkene.
144
R,..., _
R/
I
homolytic
oxonium
ion
(a) Aldehydes:
tJ'
R-C =
O~
H-C==O+R
mfe =29
basepeak
145
Mass Spectrometry
R-C
=O~
R+ + C=O
(M-29)
I
H
~-cleavage.
H",+
o
I
C-H
II
CH 2
[n-butyraldehyde] +
mle =44
(b) Ketones:
146
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
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
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
= 74 due to (II).
H 2C
+
/OH
C ..............
OCH 3
II
148
+
+
~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!
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.
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
p to
I r;/
."
R+-~-N"", ~ R
+/
+/C = N"",
150
/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.
>
mle = 106 (M-I)
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.
mle = 59
152
44 by primary amides
Co
~
'"
~+.
Rt~
~C~+
NH2
NH2
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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'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
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
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
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
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
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
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
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
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
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
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
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
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 l6HP3
C l6Hz5NO
247.0746
247.0985
248.1863
248.1162
247.9858
223
Mass Spectrometry
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
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
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
100[(M+l)]
(M)
% (M +2) = 100
[(~~2) J
Table 5.4
COMMON FRAGMENT IONS
(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
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
CK
I ~
45
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
59
,/0
II
CHz
CHPCHCH3, CH3CHCHPH, CzHsCHOH
227
Mass Spectrometry
~O
60
o
61
65
66
II
o
CsHs
=C,H"H,S, (RSSR)
67
CSH7
68
69
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
II
74
CH 2-C-OCH3 + H
o
II
II
75
76
C6HiC6HSX, C 6H4XY)
77
C6HS (C6HSX)
78
C6HS + H
79
228
Q - C H2,
80
CRSS
, + H, HBr (H SIBr at 82)
I
H
81
eLH,.
C.H,.
82
83
85
86
II
87
II
88
II
CH2-C-OC 2Hs + H
lIJ-
229
Mass Spectrometry
91
lfH2(C6HSCH2Br)'lfH + H, ~ + 2H,
92
93
([)c
I /.
H2,
g-CH,
+ H,
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
o
101
II
C-OC 4 H 9
o
102
II
CH 2 C-OC3H7 + H
o
103
II
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
123
125
127
128
HI
232
130
o
.
II
131
C3FS' -CH=CH-C
135
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
Inference Structure
2H
15
CH 3
16
17
HO
18
19
20
HF
26
CH=CH:CH=N
27
28
29
30
31
32
CHPH,S
33
34
H2S (thiols)
35
CI
36
HCI,2H20
37
38
C3 H2, C2N,
39
C3H3, HC 2N
40
CH 3C=CH
41
CH 2=CHCH 2
F2
234
H)
C-
/"-.
42
43
C3H 7' (propyl ketones, ArCH2---C3H 7), CH 3---C (methyl ketones, CH3CG,
II
where G
CH 2=CH2), HCNO
44
45
47
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
57
58
46
59
'CHF2
II
II
CHPC", CH 3-C-NH2'
60
II
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)
236
third time gives C4H40r Thus, there are five Iike[y formulas for a substance
with MW = 100.
(2)
not be present.
(a) M+= 86,
ADS.
(b) M+ = 128,
(c) M+ = 156
(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
IR
Functional groups.
NMR
Carbon chain.
MS
Details
UV
1.
2.
The presence of aromatic units from the Amax 200 nm and Amax
260 nm (benzenoid) bands.
"
oJ.
4.
IR
1.
-OH; -COOH;
2.
3.
4.
5.
Carbonyl functions.
6.
238
7.
NMR
The NMR spectrum gives valuable data about the carbon chain.
PMR
1.
2.
3.
4.
5.
13C-NMR
I.
2.
3.
4.
MS
1.
239
Mass Spectrometry
3..
4.
2.
3.
4.
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
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
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
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