Infrared spectra: It is important to remember that the absence of an

absorption band can often provide more information about the

structure of a compound than the presence of a band. Be careful to avoid
focusing on selected absorption bands and overlooking
others. Use the examples linked to the table to see the profile and intensity of
bands.

Look for absorption bands in decreasing order of importance:

1.the C-H absorption(s) between 3100 and 2850 cm-1. An absorption above
3000 cm-1 indicates C=C, either alkene or aromatic. Confirm the aromatic ring
by finding peaks at 1600 and 1500 cm-1 and C-H out-of-plane bending to give
substitution patterns below 900 cm-1. Confirm alkenes with an absorption
generally at 1640-1680 cm-1. C-H absorption between 3000 and 2850 cm-1 is
due to aliphatic hydrogens.

2. the carbonyl (C=O) absorption between 1690-1760cm-1; this strong band

indicates either an aldehyde, ketone, carboxylic acid, ester, amide, anhydride
or acyl halide. The an aldehyde may be confirmed with C-H absorption from
2840 to 2720 cm-1.

3. the O-H or N-H absorption between 3200 and 3600 cm-1. This indicates
either an alcohol, N-H containing amine or amide, or carboxylic acid. For -NH2
a doublet will be observed.

4.the C-O absorption between 1080 and 1300 cm-1. These peaks are normally
rounded like the O-H and N-H peak in 3. and are prominent. Carboxylic acids,
esters, ethers, alcohols and anhydrides all containing this peak.

5.the CC and CN triple bond absorptions at 2100-2260 cm-1 are small but
exposed.

6.structure of aromatic compounds may also be confirmed from the pattern of

the weak overtone and combination tone bands found from 2000 to 1600
cm-1.
Unconjugated Alkenes • C=C–H:
- stretch: ≥ 3000 cm–1
• linear alkenes:
- C=C stretch: moderate to weak absorption at 1667-1640 cm–1

H H
H H H H H
H
H H
1640 cm–1 , moderate 1650 cm–1 , moderate
moderate
–1
1670 cm weak
weak

Alkynes

• C C stretch: weak absorption at 2260-2100 cm–1

- not observed for symmetrical alkynes (v. weak for ‘pseudo’

symmetric alkynes
- terminal alkynes (R-C C-H) absorptions are stronger than
internal (R-C C-R) absorptions

•
C C–H stretch:

- 3333–3267 cm–1
- strong, narrow (as compared to OH or NH)

examples of
C=C, C C stretches

Me OH
C
1647 1650 cm–1 (as) 2240
2120 2080
1600 cm–1 (s) 1611 1650 1650 1970 (weak)
Mononuclear Aromatic Hydrocarbons (benzene)
• Out of plane bending of aromatic C-H bonds: most informative
- 900–675 cm–1
- intense bands, strongly coupled to adjacent hydrogens on the ring
- position and number of bands gives information about the
substitution pattern (particularly useful for alkyl substituted
aromatics. Substitution of polar groups can give rise to exceptions)

disubstituted benzenes

Out of plane bending of aromatic C-H bonds

used to distinguish para, meta, ortho isomers
Alcohols

CH stretch typically occurs as a broad peak centered @ 3300 cm –1 (spanning 3550-3200 cm–1).
This peak is broad due to H-bonding
In rare cases where H-bonding is not present, the peak is sharp and at higher frequency

C–O stretching Vibrations

• Alcohols (1260-1000 cm–1)

• Phenols (1800-1260 cm–1)

primary alcohol: 1050-1085 cm-1

secondary alcohol: 1085-1125-1
tertiary alcohol: 1125-1200 cm-1

OH
~3300 cm-1
1073 cm-1

OH
~3300 cm-1
1110 cm–1

OH
~3300 cm-1
1202 cm–1
Ketones C=O stretch (see tables)
• aliphatic: ‘normal’ position of a neat aliphatic ketone is 1715 cm–1
• conjugation: shifts position to lower frequency
alkene or phenyl group causes absorption in the 1685-1666 cm–1
region. For α,β-unsaturated carbonyls, 2 absorptions may be
observed O
O O
• cyclic ketones The bond angle influences the absorption frequency of the C=O
1788 1750 1715

Aldehydes
C=O stretch (see tables)
O O
• Aliphatic aldehydes: C=O stretch at 1740-1720 cm–1
H H
• Electron withdrawing groups shift to higher frequency 1730
1685
• Conjugative groups shift to lower frequency (1710-1685 cm–1)
C–H stretch
2830–2695 cm–1 Often, two bands are observed

Carboxylic Acids O
O
OH stretch in the 3300–2500 cm–1 region centered near 3000 cm–1 alkyl aryl
O H O H
C=O stretch 1710-1680 cm-1
1720–1706 cm-1
• 1720-1705 for aliphatic acids
• 1710–1680 for conjugated acids
C=O stretch tables

aldehydes, C=O
O O
O O O O
Cl3C H O C
H
H H H H
H
1730 1768 cm–1 1688 (C=O)
1685 1690 1684 1674 1932 (C=C)

ketones, C=O
O
O O O
O O O

1684 1685 1674 1675 (C=C)

1715 1720
1685 2203 (C=O)

O O O O O
O O O O

1813 1788 1750 1715 1706

1715 1665 1687
1680
Esters
C=O stretch
• saturated aliphatic esters: C=O: 1750–1735 cm–1
• formates, α,β-unsaturated, and benzoate esters: 1730-1715 cm–1
• phenyl or vinyl esters: 1770-1780 cm–1
C–O stretches (strong absorptions; asymmetrical coupled vibrations)
• saturated aliphatic esters (except acetates): C–O: 1210–1163 cm–1
• acetates: 1240 cm–1
• α,β-unsaturated esters: 1300–1160 cm–1
• benzoate esters: 1310–1250 cm–1

O
1749 cm–1
OCH2CH3
C=O 1243 cm–1 C–O

O
1763 cm–1
O C=O

1199, 1164, 1145 cm–1 C–O

Lactones: O
effect of O 1730 cm–1
Ring sizes C=O

O 1770 cm–1
C=O

O 1823 cm–1
H3C C=O

Anhydrides
Acid Halides O • Two carbonyl stretches (symmetrical and asymmetrical)
O
R Cl
Cl O O
R O O O O O
O
1815–1785 cm–1 alkyl O alkyl
1800–1770 cm–1 R
R
1818; 1750 cm–1 1775; 1720 cm–1 1865; 1782 cm–1
amides
NH stretch(es): Primary amides produce two N-H stretch absorptions, secondary amides only one, and tetriary none.

O O one bands
Two bands
R 3500–3400 cm–1
R NH2 3520 (as), 3400 (s) cm–1 R N
H

C=O stretching (Amide I band): NH Bending (Amide II band): amide bands I and II
O O
1690 cm–1 (dilute) 1620-1590 cm–1
R NH2 R NH2
O O
1680-1700 cm–1 (dilute) 1550-1510 cm–1
R R
R N R N
H H
O
R 1680-1630 cm–1
R N
R

Lactams
O O O
NH NH
NH

1650 cm–1 1750-1700 cm–1 1760-1730 cm–1

• NH stretching
- primary amines (RNH2) display two bands, near 3500 and 3400
cm–1. These represent ‘free’ asymmetrical and symmetrical stretches.
- secondary amines (R2NH) display one band near 3350-3310 cm–1.
- weaker and sharper than OH

Nitriles

alkyl C N C N
R
2260-2240 cm–1 2240-2222 cm–1

Nitro compounds
• 2 bands from the asymmetrical and symmetrical stretching of
the N O bond

alkylNO 2 NO2
R

1550 cm -1 and 1372 cm-1 1550-1500 cm -1 and 1360-1290 cm-1