Infra-Red Spectrosco Py: Dr. Mohamed Ibrahim M. Pharm in Drug Quality Control

Infra-Red
spectrosco
py11
Lecture
Dr. Mohamed Ibrahim
M. pharm in drug quality control
tation
Infrared spectroscopy
There are two common type of instrument:

 Dispersive instrument: which use monochromator to select
wavenumber in order to monitor its intensity after the radiation has
passed through the sample.
 Fourier transform instrument: which use an interferometer (generate
radiation source in individual wavenumber.
Schematic diagram of a continuous wave IR instrument.
Made of metal oxide; Made of alkali metal

Zirocomium; yttrium halides
and thorium
The advantage of Fourier transform IR

technique is that a full spectral scan can
be acquired in about 1 s.
Also, because the instrument is attached

to a computer, several spectral scans can
be taken and averaged in order to improve
the signal : noise ratio for the spectrum.
Infrared Instrumentation:
IR Source Sample compartment Detector
Analyzing
IR
Spectra
The four primary regions of the IR spectrum:
4000 cm-1 2700 cm-1 2000 cm-1 1600 cm-1 600 cm-1
Concentrate on the functional group region above 1500 cm −1, and examine
the two sections where double and triple bonds absorb.
A C=C absorbs at ~1650 cm−1.
A C=O absorbs between 1650 and 1800 cm −1, often around
1700 cm−1.
A C≡C or C≡N absorbs at ~2250 cm−1.
1. IR Absorptions in Hydrocarbon:
 The IR spectra of hexane, 1-hexene, and 1-hexyne:
 The important differences that characterize the IR spectra of hydrocarbons above 1500
cm–1. Although all three compounds contain C – C bonds and sp3 hybridized C – H
bonds.
 The absorption peaks due to C = C and C ≡ C readily distinguish the alkene and alkyne
The alkane CH3CH2CH2CH2CH2CH3 has
only C – C single bonds and sp3 hybridized
C atoms.
Therefore, it has only one major absorption
above 1500 cm–1, its C sp3 – H absorption at
3000–2850 cm–1
The alkene CH2=CHCH2CH2CH2CH3
has a C=C and Csp2 – H, in addition to its

sp3 hybridized C atoms.
Therefore, there are three major absorptions

above 1500 cm–1:
 C sp2 – H at 3150–3000 cm–1
 Csp3 – H at 3000–2850 cm–1
 C = C at 1650 cm–1
The alkyne HC≡CCH2CH2CH2CH3
has a C≡C and Csp – H, in addition to its sp3

hybridized C atoms.
Therefore, there are three major absorptions:
 C sp – H at 3300 cm–1
 C sp3 – H at 3000–2850 cm–1
 C ≡ C at ~2250 cm–1
Aromatic Compounds:
An aromatic compound like
isopropylbenzene contains a benzene
ring and Csp2—H, in addition to its
sp3 hybridized C atoms.
Thus, there are three major
absorptions:
 Csp2—H at 3150−3000 cm−1
 Csp3—H at 3000−2850 cm−1
 Benzene ring at 1600, 1500 cm−1
Ethyl benzene
H
Aromatics
 Due to the delocalization of e- in the ring, is slightly lower in energy
than normal C=C
 These show up as a pair of sharp bands, 1500 & 1600 cm-1, (lower
frequency band is stronger)
 C-H bonds off the ring show up similar to vinyl C-H at 3000-3100 cm-1
Infrared group analysis: ethyl benzene
(w – m)
(w – m)
G
Mono substituted
G
G
1,2 disubstituted (ortho or o-)
G
1,2 disubstituted (meta or m-)

G
G
1,4 disubstituted (para or p-)

G
Example: What types of bonds are responsible for the absorptions above
1500 cm−1 in compounds A and B?
Solution:
 Compound A has two major absorptions above 1500 cm−1:
The absorption at ~3000 cm−1 is due to C—H bonds and the absorption at ~1700
cm−1 is due to a C=O group. Because the C—H absorption occurs at < 3000
cm−1, all C—H bonds contain sp3 hybridized C atoms.
Compound B has two major absorptions above 1500 cm−1:
The absorption at ~3000 cm−1 is due to Csp3—H bonds and the absorption at
~2250 cm−1 is due to a triple bond, either a C≡C or a C≡N.
O-containing compounds:
The most important IR absorptions for

oxygen-containing compounds occur at
3600−3200 cm−1 for an OH group and at
approximately 1700 cm−1 for a C=O.
Alcohols: The most prominent absorption
for an alcohol like butan-2-ol is the broad,
strong absorption at 3600−3200 cm−1 due
to the OH group.
Ethers: An ether like diethyl ether has neither an OH group nor a C=O, so
its only absorption above 1500 cm −1 occurs at ~3000 cm−1, due to sp3
hybridized C—H bonds.
Compounds that contain an oxygen atom but do not show an OH or C=O

absorption are ethers.
Aldehydes: An aldehyde like propanal has a C=O and Csp2—H. In addition
to the absorption of its Csp3—H , there are two major absorptions:
 A highly unique sp2 C-H stretch appears as a doublet, 2720 & 2820
cm-1
 C=O at ~1700 cm−1
Ketones: In addition to the absorption of its Csp3—H, a ketone like butan-2-one
has one major absorption:
 C=O at ~1700 cm−1
Carbnyl absorption of cyclic ketones shifts to a higher or shorter wavenumber.

Carboxylic Acids: A carboxylic acid like butanoic acid has two

characteristic IR absorptions in addition to the absorption of its Csp3—H :
 O—H at 3500−2500 cm−1, a broad, strong absorption that almost

obscures the C—H peak at ~3000 cm−1.
 C=O at ~1710 cm−1
Esters: In addition to the
absorption of its Csp3—H, an
ester like methyl propanoate has
one major absorption:
 C=O at ~1745−1735 cm−1

3. N-containing compounds:
Amine: An amine like alcohol has characteristic absorptions in addition
to the absorption of its Csp3—H :
 N—H stretching peaks at 3400−3200 cm−1 (one or two peaks)

Amides:
An amide like propanamide has three

characteristic absorptions in addition to
the absorption of its Csp3—H :
 N—H stretching peaks at

3400−3200 cm−1 (one or two peaks)
 C=O at 1680−1630 cm−1
Nitriles:
The C≡N group of a nitrile like
octanenitrile absorbs in the triple
bond region at ~2250 cm−1.

1.
Example:
How can the two isomers having molecular formula
C2H6O be distinguished by IR spectroscopy?
Solution
First, draw the structures of the compounds and
then locate the functional groups. One compound
is an alcohol and one is an ether.
Although both compounds have sp3 hybridized C—H bonds, ethanol has
an OH group that gives a strong absorption at 3600−3200 cm−1, and
dimethyl ether does not.
Problem
How do the three isomers of molecular formula
C3H6O (A, B, and C) differ in their IR spectra?
Problem
How can IR spectroscopy be used to determine
when the following reaction is complete?
Analyzing IR spectra
 problem: Which compound—A, B, or C—gives rise to the given IR

spectrum?

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Infra-Red

There are two common type of instrument:

Made of metal oxide; Made of alkali metal

The advantage of Fourier transform IR

Also, because the instrument is attached

The four primary regions of the IR spectrum:

 The IR spectra of hexane, 1-hexene, and 1-hexyne:

The alkane CH3CH2CH2CH2CH2CH3 has

only C – C single bonds and sp3 hybridized

Therefore, it has only one major absorption

above 1500 cm–1, its C sp3 – H absorption at

The alkene CH2=CHCH2CH2CH2CH3

has a C=C and Csp2 – H, in addition to its

Therefore, there are three major absorptions

 C sp2 – H at 3150–3000 cm–1

 Csp3 – H at 3000–2850 cm–1

The alkyne HC≡CCH2CH2CH2CH3

has a C≡C and Csp – H, in addition to its sp3

Therefore, there are three major absorptions:

 C sp3 – H at 3000–2850 cm–1

Infrared group analysis: ethyl benzene

1,2 disubstituted (meta or m-)

1,4 disubstituted (para or p-)

The most important IR absorptions for

Compounds that contain an oxygen atom but do not show an OH or C=O

Aldehydes: An aldehyde like propanal has a C=O and Csp2—H. In addition

to the absorption of its Csp3—H , there are two major absorptions:

Ketones: In addition to the absorption of its Csp3—H, a ketone like butan-2-one

has one major absorption:

 C=O at ~1700 cm−1

Carbnyl absorption of cyclic ketones shifts to a higher or shorter wavenumber.

Carboxylic Acids: A carboxylic acid like butanoic acid has two

 O—H at 3500−2500 cm−1, a broad, strong absorption that almost

Esters: In addition to the

absorption of its Csp3—H, an

ester like methyl propanoate has

one major absorption:

 C=O at ~1745−1735 cm−1

Amine: An amine like alcohol has characteristic absorptions in addition

to the absorption of its Csp3—H :

 N—H stretching peaks at 3400−3200 cm−1 (one or two peaks)

An amide like propanamide has three

 N—H stretching peaks at

The C≡N group of a nitrile like

octanenitrile absorbs in the triple

bond region at ~2250 cm−1.

 problem: Which compound—A, B, or C—gives rise to the given IR

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