- __ -"'-'=_ ..

--:11

-:

es

listing of Some Functional Groups and Classes of Compounds

rption Frequencies in the Infrared
Frequency Ranges
(cm:t) and
Intensities *

or Class

R-C

X
1810-1790 (s)
965-920 (m)
440-420 (s)
1785-1765 (s)

omatic

890-850

-CH2OH

Secondary

-CHROH

Tertiary

-CRPH

General

-OH

Aldehydes

(s)

1440-1260 (m-s, b r)
700-600 (m-s, br)
2830-2810 (m)}
2740-2720 (rn)
1725-1695 (vs)
1440-1320 (s)
695-635 (s)
565-520 (s)

Fermi doublet; CH stretch with overtone

of CH bend
C=O stretch; slightly higher in CCI4 soln
H-C=O
bend in aliphatic aldehydes
C-C-CHO
bend
C-C=O
bend

(s)
(s)
(s)
(s)

3620-3610
1160-1120
3350-3250

(s)
(s)
(s)

Tetrasubst

\
C=CHI
\
I
C=C
I
\

Alkyl

Alkynes

RC=C-H

Amides
Primary

Secondary

See Vinyl
See Vinylene

C=CH

-CONH2

-CONHR

C=O stretch; fluorides 50 cm-1 higher

C-C stretch
CI-C=O
in-plane deformation
C=O stretch; also a weaker band (17501735 crrr ") due to Fermi resonance
C-C stretch (Ar-C) or C-CI stretch
OH stretch, dil CCI4 soln
C-OH stretch; lowered by unsaturation
OH stretch, dil CCI4 sol n
C-OH stretch; lower when R is a branched
chain or cyclic
OH stretch, dil CCI4 sol n
C-OH stretch; lower when R is branched
OH stretch; broad band in pure solids or
liquids
C-OH in-plane bend
C-OH out-of-plane deformation

3640-3630
1060-1030
3630-3620
1120-1080

Alkenes
Monosubst
-CH=CH2
Disubst
-CH=CH-

Trisubst

and Remarks

Il

~atic

hols
::r'imary

Assignment

See Vinylidene

3050-3000 (w)
1690-1655 (w-m)
850-790 (m)

CH stretch
C=C stretch
CHout-of-plane bending

1690-1670

C=C stretch, may be absent for symmetrical compounds

(w)

2980-2850 (m)
1470-1450 (m)
1400-1360 (m)
740-720 (w)

CH stretch, several bands

CH2deformation
CH3 deformation
CH2rocking

3300-3250 (m-s)
2250-2100 (w-m)
680-580 (s)

Terminal -C-H
stretch
C-C, frequency raised by conjugation
-C-CH
bend

3540-3520
3400-3380
1680-1660
1650-1610

(m)
(m)

1420-1400
3440-3420

(m-s)

NH2stretch (dil solns); bands shift to

3360-3340 and 3200-3180 in solid
C=O stretch (Amide I band)
NH2deformation; sometimes appears as a
shoulder (Amide II band)
C-N stretch (Amide III band)
NH stretch (dil soln); shifts to 3300-3280 in
pure liquid or solid
C=O stretch (Amide I band)
NH bend (Amide II band)
C-N stretch
Assignment uncertain

(vs)
(m)

(m)

1680-.1640 (vs)
1560-1530 (vs)
1310-1290 (m)
710-690 (rn)
*KEV: s = strong; m = medium; w = weak; v = very; br = broad.

Continued

Part II/Vibrational

190

Spectroscopy

TABLE 8-2
An Alphabetical Listing of Some Functional Groups and Classes of Compounds
with Their Absorption Frequencies in the Infrared-cont'd
Frequency Ranges
(crrt:') and
Groups or Class

intensities"

Amides-cont'd
Tertiary
-CONR2
General
-CONR2
Amines
Primary

-NH2

Secondary

Tertiary

1670-1640
630-570
615-535
520-430

Assignment

C=O stretch
N-C=O
bend
C=O out-of-plane bend
C-C=O
bend

(vs)

(s)
(s)
(m-s)

2830-2810 (rn)
1650-1590 (s)
3350-3300 (vw)
1190-1130 (m)
740-700 (m)
450-400 (w, br)
510-480 (s)

NH stretch; broad band, may have some

structure
CH stretch
NH2deformation
NH stretch
C-N stretch
NH deformation
C-N-C
bend
C-N-C
bend

2800-2300 (m-s)
1600-1500 (m)

NH3+ stretch, several peaks

NH deformation (one or two bands)

3200-3000 (s)

H-bonded NH2and OH stretch; v broad band

in solid state

1600-1590 (s)
1550-1480 (m-s)
1425-1390 (w-m)
560-500 (s)
3350-3050 (vs)
1430-1390 (s)

COO- antisym stretch

-NH/
deformation
COO- sym stretch
COO- rocking
NH stretch; broad band
NH2deformation; sharp peak

1850-1780 (variable)
1770-1710 (m-s)
1220-1180 (vs)

Antisym C=O stretch

Sym C=O stretch
C-O-C
stretch (higher in cyclic anhydrides)

3460-3280 (m)

-NHR

-NR2

Amine hydrohalides

RNH +X+ 3

R'NH2RX-

and Remarks

iH2
Amino acids

-C-COOH

Anhydrides

-CO

\0
/

-CO
Aromatic compounds

3100-3000 (m)
2000-1660 (w)
1630-1430 (variable)
900-650 (s)
580-420 (rn-s)

Azides

-N=N=N

Bromo
-C-Br,
tert-Butyl (CH3)3C-

2160-2080 (s)

2150-2100

Carbonyl

1870-1650 (vs, br)

\C=O

/
Carboxylic acids

I
I

-C-CI

Cycloalkanes

stretch

C-Br stretch
CH stretch; several bands
CH3deformations
N=C=N

(vs)

antisym stretch

C=O stretch

------~
I

'3550-3500 (s)
3300-2400 (s. v or)
1800-1740(s)
,

700-590 (s)
550-465 (s)

OH stretch (monomer, dil soln)

H-bonded OH stretch (solid and liquid states)
C~O stretch of monomer (dil soln)
C=O stretch of dimer (solid and liquid states)
960-910 (s)
C-OH deformation
O-C=O
bend
C-C=O
bend

850-550 (m)

C-CI

580-430 (s)

Ring deformation

~~

Chloro

Aromatic ring stretching (four bands)

Out-of-plane CH deformations (one or two
bands depending on substitution)
Ring deformations (two bands)
N=N=N

650-500 (rn)
2980-2850 (m)
1400-1370 (rn)
and 1380-1360 (s)

Carbodiimides
-N=C=N-

CH stretch, several peaks

Overtone and combination bands

stretch

ical Listing of Some Functional Groups and Classes of Compounds

sorption Frequencies in the Infrared-cont'd

..=-oups

-::--ers

or Class

.-C-O-C-

_ -oalkvl
-CF3' -CH2-,
etc.
_ yanates -N=C=O
sothiocyanates
etones
R

-N=C=S

\=0

R/

Frequency Ranges
(cm='} and
Intensities *

Assignment

and Remarks

2300-2240 (s)

N=N stretch

1765-1720 (vs)
1290-1180 (vs)
645-575 (s)

C=O stretch
C-O-C
antisym stretch
O-C-O
bend

1280-1220
1140-1110
1275-1200
1250-1170
1050-1000

C-O-C
stretch in alkyl aryl ethers
C-O-C
stretch in dialkvl ethers
C-O-C
stretch in vinyl ethers
C-O-C
stretch in cyclic ethers
R(alkyl)-C-O
stretch in alkyl aryl ethers

(s)

(vs)
(vs)
(s)
(s)

1400-1000 (vs)

C-F

2280-2260 (vs)

N=C=O

2140-2040
1725-1705
1700-1650
1705-1665
and 1650-1580

(vs, br)
(vs)
(vs)
(s)

(m)

stretch
stretch

C=N=S antisym stretch

C=O stretch in saturated aliphatic ketones
C=O stretch in aromatic ketones
C=O and C=C stretching in
a,~-unsaturated ketones

Lactones

1850-1830 (s)
1780-1770 (s)
1750-1730 (s)

C=O stretch in ~-Iactones

C=O stretch in y-Iactones
C=O stretch in 8-lactones

Methyl

2
-2850 (s)
2835-28
s
2820s)
1470-1440 (rn)
1390-1370 (m-s)

CH stretch in C-CH3 compounds

CH stretch in methyl ethers .(0-CH3)
CH stretch in N-CH3 compounds
CH3antisym deformation
CH3 sym deformation

-CH3

Methylene

-CH2-

Naphthalenes

Nitriles

Nitro

-C=N

-N02

2940-2920
and 2860-2850
3090-3070
and 3020-2980
1470-1450

(m)

(m)
(rn)
(m)
(m)

645-615 (m-s)
and 545-520 (s)
490-465 (variable)
2260-2240 (w)
2240-2220 (rn)
580-530 (m-s)
1570-1550 (vs)
and 1380-1360 (vs)
1480-1460 (vsl"{
and 1360-1320 (vsU
920-830 (m)
650-600 (s)
580-520 (m)
530-470 (m-s)

CH stretches in alkanes
CH stretches in alkenes
CH2 deformation
In-plane ring bending
Out-of-plane ring bending
C-N stretch in aliphatic nitriles
C-N stretch in aromatic nitriles
C-C-CN
bend
N02 stretches in aliphatic nitro compounds
N02 stretches in aromatic nitro compounds
C-N stretch
N02 bend in aliphatic compounds
N02 bend in aromatic compounds
N02 rocking

Oximes

=NOH

3600-3590 (vs)
3260-3240 (vs)
1680-1620 (w)

OH stretch (dil soln)

OH stretch (solids)
C=N stretch; strong in Raman

Phenols

Ar-OH

720-600 (s, br)

450-375 (w)
3100-3000 (w-m)
2000-1700 (w)

O-H out-of-plane deformation

C-OH deformation
CH stretch
Four weak bands; overtones and combinations
Continued

TABLE 8-2
An Alphabetical Listing of Some Functional Groups and Classes of Compounds
with Their Absorption Frequencies in the Infrared-cont'd

Groups or Class
Phenyl-co nt' d

Phosphates
R = alkyl

Frequency Ranges
(crrr+) and
Intensities *

Phosphines

1625-1430 (m-s)
1250-1025 (m-s)
770-730 (vs)
710-690 (vs)
560-420 (m-s)

Aromatic C=C stretches (four bands)

CH in-plane bending (five bands)
CH out-of-plane bending
Ring deformation
Ring deformation

1285-1255 (vs)
1050-990 (lis)
1315-1290 (vs)
1240-1190 (vs)

P=O stretch
P-O-C
stretch
P=O stretch
P-O-C
stretch

-PH2, -PH

2410-2280 (m)
1100-1040 (w-m)
700-650 (m-s)

P-H stretch
P-H deformation
P-C stretch

3080-3020 (m)
1620-1580 (vs)
and 1590-1560 (vs)
840-720 (s)
635-605 (m-s)
Silanes

-SiH3
-SiH2Silanes (fully substituted)

R-O-S02-O-R

R-O-S03-M+
(M = Na ' , K+, etc.)
Sulfides

C-S-

Sulfones

-S0zOH

\
s=o
/

Sulfoxides
Thiocyanates

-S-C=N

-S-H

Triazines
C3N2Y3
1,3,4,5-trisubst
Vinyl

-CH=CH2

Vinylene

.Vinylidene

\
/

C=CH
2

C-C

and C-N

stretches

CH out-of-plane deformation (one or two

bands, depending on substitution)
In-plane ring bending
Si-H
Si-H

1280-1250 (m-s)
1110-1050 (vs)
840-800 (m)

Si-C stretch
Si-O-C
stretch (aliphatic)
Si-O-C
deformation

1140-1350 (s)
and 1230-1150 (s)
1260-1210 (vs)
and 810-770 (s)

S-O

stretch
deformation

stretches in covalent sulfates

S=O stretches in alkyl sulfate salts

C-O-S
stretch
C-S

stretch

1360-1290 (vs)
1170-1120 (vs)
610-545 (ms)

S02 antisym stretch

S02 sym stretch
S02 scissor mode

1250-1150 (vs, br)

S=O stretch

1060-1030'(s, br)
610-545 (m-s)

S=O stretch
S02 scissoring

2175-2160 (m)
650-600 (w)
405-400 (s)

C=N stretch
S-CN stretch
S-C=N
bend

2590-2560 (w)
700-550 (w)

S-H
C-S

1600-1500 (vs)
1380-1350 (vs)
820-800 (s)

Ring stretching
Ring stretching
CH out-of-plane deformation

3095-3080 (rn)
and 3030-2980 (w-m)
1850-1800 (w-m)
1645-1615 (m-s)
1000-950 (s)
950-900 (vs)

-CH=CH-

CH stretch

2160-2110 (m)
950-800 (s)

710-570 (m)

-S02-

Sulfonic acids

Thiols

and Remarks

(RO)3P=0

R = aryl

Sulfates

Assignment

stretch; strong in Raman

stretch; strong in Raman

=CH2 stretching
=CH stretching
Overtone
of CH2out-of-plane wagging
C=C stretch
CH out-of-plane deformation
CH2out-of-plane wagging

3040-3010 (m9
1665-1635 (w-m)
1675-1665 (w-m)
730-665 (s)
980-955 (s) .

=CH2 stretching
C=C stretch (cis isomer)
C=C stretch (trans isomer)
CH out-of-plane deformation (cis isomer)
CH out-of-plane deformation (trans isomer

3095-3075 (m)
1665-1620 (w-m)
895-885 (s)

=CH2 stretching
C=C stretch
CH2out-of-plane wagging