Introduction to Interpretation of Infrared

Spectra
IR Spectroscopy is an extremely effective method for determining the presence or
absence of a wide variety of functional groups in a molecule. (For a detailed listing, see
the table showing important IR absorptions of various functional groups.) One way to
begin analyzing an IR spectrum is to start at the high wave number end of the spectrum
(typically 4000 cm-1) and look for the presence and absence of characteristic absorptions
as you move toward lower wave numbers. Some of the most common, and distinctive,
absorptions are organized into several regions below. This is the type of analysis that you
should be able to do without consulting notes. If necessary, a more detailed analysis could
then be attempted by consulting a text on IR interpretation.

Important Regions of the IR Spectrum

3600-2700 cm-1
X-H stretch region

The alcohol OH stretch is usually a broad and

Alcohol O-H strong absorption near 3400. The NH stretch is
Amine or Amide N- typically not as broad or strong as the OH, and in
3600-3300 cm-1
H the case of an NH2 it may appear as two peaks.
Alkyne C-H The terminal alkyne C-H may be confirmed by a
weak CC triple bond stretch near 2150 cm-1
This is normally a very broad signal centered
3300-2500 cm-1 Acid O-H
near 3000 cm-1.
The aromatic CH's usually appear as a number of
-1 Aromatic (sp2) =C-H
3200-3000 cm weak absorptions, while the alkene C-H is one or
Alkene (sp2) =C-H
a couple stronger absorptions.
Almost all organic compounds have alkyl CH's
so this is not usually too informative. However,
-1 3
3000-2800 cm Alkyl (sp ) C-H the intensity of these peaks relative to other
peaks gives a hint as to the size of the alkyl
group.
Two medium intensity peaks on the right hand
-1
2850 and 2750 cm Aldehyde C-H shoulder of the alkyl C-H's. Look for confirming
carbonyl C=O peak.

2300-2100 cm-1

2260-2210 A sharp, medium intensity peak. Carbon Dioxide in the

 atmosphere may also result in an absorption in this area if not
cm-1
subtracted out.
This peak's intensity varies from medium to nothing. Since the
2260-2100
intensity is related to the change in dipole moment, symmetrical
cm-1
alkynes will show little or no absorption here!

1850-1500 cm-1
C=X stretch region

Anhydrides have two absorptions, one near 1830-1800

Anhydride C=O and one near 1775-1740. The absorption frequency
1850-1750
3-4 membered ring C= increases as the ring size decreases. For example:
cm-1
O cyclohexanone=1715, cyclopentanone=1745,
cylobutanone=1780, cyclopropanone=1850.
Aldehyde C=O
1750-1700 Ketone C=O This is usually the most intense absorption in the
cm-1 Ester C=O spectrum.
Acid C=O
Because of the weakening of the C=O due to resonance,
1700-1640 Amide C=O amides and conjugated carbonyl's come slightly lower
cm-1 Conjugated C=O than "normal" C=O. In general, conjugation lowers the
absorption by 20-50 cm-1.
This absorption is not as intense as that seen for C=O. It
1680-1620 is variable and may be fairly small in symmetrical, or
-1 Alkene C=C
cm nearly symmetrical cases. Look for confirming alkene
C-H peaks above 3000.
Multiple sharp, medium peaks. The pattern of peaks
varies depending upon the substitution pattern. Usually
1600-1400
Aromatic C=C there is one peak around 1600 and several others at
cm-1
lower wavenumbers. Look for confirming aromatic C-H
peaks slightly above 3000.

1500-400 cm-1
Fingerprint Region

1300-1000
C-O A strong absorption.
cm-1
The large number of different vibrations that occur here complicates
interpretation of peaks in the fingerprint region. These include single
1500-400 c
Various bond stretches and a wide variety of bending vibrations. This region
m-1
gets its name since nearly all molecules (even very similar ones) have
a unique pattern of absorptions in this region.
Wave number of Absorption

The absorption wave number for a stretching vibration is related to both the force
constant between the two atoms (k) and the mass of the two atoms (m1 and m2) by the
Hooke's Law equation:

From this relationship, two important trends in the wave number for stretching vibrations
can be deduced.

1. As the bond strength increases, the wave number increases. For example:

2. As the mass of one of the two atoms in the bond increases, the wave number
decreases. (Assuming the change in bond strength is relatively small.) For
example:

Intensity of Absorption

The intensity of an absorption in the IR spectrum is related to the change in dipole that
occurs during the vibration. Consequently, vibrations that produce a large change in
dipole (e.g. C=O stretch) result in a more intense absorption than those that result in a
relatively modest change in dipole (e.g. C=C). Vibrations that do not result in a change in
dipole moment (e.g., a symmetrical alkyne C triple bond C stretch) will show little or no
absorption for this vibration.