APLIKASI INFRA MERAH DALAM

BIDANG FARMASI

Muhammad Taupik
Laboratorium Kimia Analisis
Farmasi UNG
 Typical Infrared Absorption
Regions
WAVELENGTH (m)
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
C C
Symmetric Stretch
H ~2853 cm-1 H

H H H
C Asymmetric Stretch
C
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 ~1465 cm-1
H H H ~1250 cm-1

C C C
H H

H ~720 cm-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
 Typical Infrared Absorption
Regions
O-H WAVELENGTH (m)
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)
 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

R R
O H O
H H
Many kinds of OH
bonds of different
lengths and strengths
This leads to a broad
absorption.

R O O
R 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

C Cl4 well-defined length
and strength.
C C l4
R O CC l4
H
C Cl4
CC l4
Solvent molecules
surround but do not
hydrogen bond.

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

 ALCOHOL

Cyclohexanol
neat solution

O-H OH 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
R C C R
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
 Typical Infrared Absorption
Regions
N-H WAVELENGTH (m)
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)
 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