IR Analisis Kualitatif

APLIKASI INFRA MERAH DALAM
BIDANG FARMASI
Penggunaan Infra merah
Analisis kualitatif (elusidasi struktur)

Analisis kuantitatif
Quality Control
Typical Infrared Absorption
Regions
WAVELENGTH (mm)
2.5 4 5 5.5 6.1 6.5 15.4
O-H C-H C N C=O C=N C-Cl

Very C-O
N-H C C few C=C
C-N
X=C=Y bands C-C
(C,O,N,S) N=O N=O *
4000 2500 2000 1800 1650 1550 650

FREQUENCY (cm-1)
BASE VALUES
Guideposts for you to memorize.

BASE VALUES These are
the minimum
(+/- 10 cm-1) number of
values to
memorize.
O-H 3600
N-H 3400
C-H 3000
C N 2250
C C 2150
C=O 1715
C=C 1650
C O ~1100 large range
C-H STRETCH
The C-H stretching region
BASE VALUE = 3000 cm-1
• C-H sp stretch ~ 3300 cm-1

UNSATURATED
• C-H sp2 stretch > 3000 cm-1
3000 divides
• C-H sp3 stretch < 3000 cm-1 SATURATED

STRONGER BONDS HAVE LARGER FORCE CONSTANTS
AND ABSORB AT HIGHER FREQUENCIES
increasing frequency (cm-1)
3300 3100 3000 2900
=
=C-H =C-H -C-H
sp-1s sp2-1s sp3-1s
increasing CH Bond Strength

increasing force constant K
CH BASE VALUE = 3000 cm-1
METHYLENE GROUP STRETCHING VIBRATIONS
Two C-H bonds share a central carbon
(hydrogens attached to the same carbon)
H H H H
C C C Symmetric Stretch
H H ~2853 cm-1
H H H H
C C C Asymmetric Stretch
H ~2926 cm-1
H
Any time you have two or more of the same kind of bond sharing
a central atom you will have symmetric and asymmetric modes.
METHYL GROUP STRETCHING VIBRATIONS
Three C-H bonds share a central carbon
(hydrogens attached to the same carbon)
H
C H Symmetric Stretch
H ~2872 cm-1
H
C H Asymmetric Stretch
~2962 cm-1
H
ALKANE
Hexane
CH bending vibrations
discussed shortly
CH includes
stretching CH3 sym and asym
vibrations CH2 sym and asym
CH3 CH2 CH2 CH2 CH2 CH3
C-H BENDING
THE C-H BENDING REGION
• CH2 bending ~ 1465 cm-1
• CH3 bending (asym) appears near

the CH2 value ~ 1460 cm-1
• CH3 bending (sym) ~ 1375 cm-1

METHYLENE GROUP BENDING VIBRATIONS
Scissoring Wagging
H-1
~1465 cm
H H H ~1250 cm-1
C C C
H H
~720 cmH
-1
H H H ~1250 cm-1
C C C
H H
Rocking Twisting
Bending
Vibrations
ALKANE
Hexane
CH2
rocking
CH3
CH2 bend
bend
CH
stretch
CH3 CH2 CH2 CH2 CH2 CH3

ALKENE
1-Hexene
=CH
C=C CH2
CH3
bend
CH CH oops
CH2 CH CH2 CH2 CH2 CH3
AROMATIC
Toluene
Ar-H CH3
CH3 C=C
benzene
Ar-H oops
ALKYNE
1-Hexyne
=
C=C
CH2, CH3
= C-H HC C CH2 CH2 CH2 CH3

=C-H
O-H STRETCH
Regions
O-H WAVELENGTH (mm)
2.5 4 5 5.5 6.1 6.5 15.4

Very C-O
N-H C C few C=C
C-N
X=C=Y bands C-C
(C,O,N,S) N=O N=O *
4000 2500 2000 1800 1650 1550 650

FREQUENCY (cm-1)
The O-H stretching region
• O-H 3600 cm-1 (alcohol, free)
• O-H 3300 cm-1 (alcohols & acids,
H-bonding)
broadens
shifts
FREE H-BONDED
3600 3300
Effect of Hydrogen-Bonding
on O-H Stretching
Free
OH
Free C-H
OH
H-bonded H-bonded
OH C-H OH C-H
4000 3600 3200 2800 4000 3600 3200 2800 4000 3600 3200 2800
(a) Pure Liquid (b) Dilute Solution (c) Very Dilute Solution
“neat”
1-Butanol
HYDROGEN-BONDED HYDROXYL
Many kinds of OH
R R bonds of different
lengths and strengths
O H O This leads to a broad
H H
absorption.
R O R O O
H R
“Neat” solution.
H
O
R H Longer bonds are weaker
and lead to
lower frequency.
Hydrogen bonding occurs in concentrated solutions

( for instance, undiluted alcohol ).
“FREE” HYDROXYL
The “free” hydroxyl vibrates without interference from any
other molecule.
Distinct bond has a

CCl4 well-defined length
and strength.
CCl4
R O CCl4
H
CCl4
CCl4
Solvent molecules
surround but do not
hydrogen bond.
Occurs in dilute solutions of alcohol in an “inert” solvent like CCl4.

ALCOHOL
Cyclohexanol
neat solution
OH
O-H CH2
H-bond
C-O
C-H
CARBOXYLIC ACID
Butanoic
neat solution
Acid
O-H
H-bond
C-O
CH2 O
C-H C=O CH3 CH2 CH2 C OH

CARBOXYLIC ACID DIMER
O H O
C R
R C
O H O
Strong hydrogen bonding in the dimer weakens the OH

bond and leads to a broad peak at lower frequency.
N-H STRETCH
Regions
N-H WAVELENGTH (mm)
2.5 4 5 5.5 6.1 6.5 15.4

Very C-O
N-H C C few C=C
C-N
X=C=Y bands C-C
(C,O,N,S) N=O N=O *
4000 2500 2000 1800 1650 1550 650

FREQUENCY (cm-1)
The N-H stretching region
N-H 3300 - 3400 cm-1
• Primary amines give two peaks

H H
N N
H H
symmetric asymmetric
• Secondary amines give one peak

• Tertiary amines give no peak
PRIMARY AMINE
aliphatic
1-Butanamine
NH2
scissor CH3
CH2
NH2
CH3 CH2 CH2 CH2 NH2

PRIMARY AMINE
aromatic
3-Methylbenzenamine
-CH3
Ar-H NH2
NH2
benzene
CH3 Ar-H
oops
SECONDARY AMINE
N -Ethylbenzenamine
NH
NH CH2 CH3
CH3
Ar-H
benzene
oops
TERTIARY AMINE
N,N -Dimethylaniline
Ar-H
-CH3
CH3
no N-H
N
CH3
CH3
benzene Ar-H
oops
Contoh spektra molekul obat

IR Analisis Kualitatif

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APLIKASI INFRA MERAH DALAM

Analisis kualitatif (elusidasi struktur)

O-H C-H C N C=O C=N C-Cl

4000 2500 2000 1800 1650 1550 650

Guideposts for you to memorize.

• C-H sp stretch ~ 3300 cm-1

• C-H sp3 stretch < 3000 cm-1 SATURATED

3300 3100 3000 2900

sp-1s sp2-1s sp3-1s

increasing CH Bond Strength

• CH2 bending ~ 1465 cm-1

• CH3 bending (asym) appears near

• CH3 bending (sym) ~ 1375 cm-1

CH3 CH2 CH2 CH2 CH2 CH3

= C-H HC C CH2 CH2 CH2 CH3

O-H C-H C N C=O C=N C-Cl

4000 2500 2000 1800 1650 1550 650

Hydrogen bonding occurs in concentrated solutions

Distinct bond has a

Occurs in dilute solutions of alcohol in an “inert” solvent like CCl4.

C-H C=O CH3 CH2 CH2 C OH

Strong hydrogen bonding in the dimer weakens the OH

O-H C-H C N C=O C=N C-Cl

4000 2500 2000 1800 1650 1550 650

• Primary amines give two peaks

• Secondary amines give one peak

CH3 CH2 CH2 CH2 NH2

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