Identification of Compounds: Uv, Ir, NMR and Mass Spectrometries

Identification of Compounds
by UV, IR, NMR AND MASS SPECTROMETRIES
Gas Chromatogram of Flavor Compounds

1 10 11 17
3 13 15 8 5 16
6 9 12 14
Identification of Compound
H3C H2 H2 H CH3 H H H H CH3
O
CH3
SPECTROMETRIC IDENTIFICATION
I. II. III. IV. V.
Introduction of Spectrometric Analyses Ultra Violet Spectrometry Infrared Spectrometry Nuclear Magnetic Resonance Spectrometry Mass Spectrometry
I. Introduction of Spectrometric Analyses
The study how the sample interacts with different wavelength in a given region of electromagnetic radiation is called spectroscopy or spectrochemical analysis. The collection of measurements signals (absorbance) as a function of electromagnetic radiation is called a spectrum.
Spectrum of Radiation
Electromagnetic Spectrum.
Wavelength, cm , 10-10 10-8 10-6 10-4 ultraviolet visible 10-2 1 microwave 102 104 106 108
infrared
1020
1018
1016
1014
1012
1010
108
106
104
102
frequency, (cycles/sec) , yellow orange violet green visible region
blue
400
500
600 700 Wavelength, nm ,
red
800
Power
ray
ray
radio
Energy Absorption
The mechanism of absorption energy is different in the Ultraviolet, Infrared, and Nuclear Magnetic Resonance regions. However, the fundamental process is the absorption of certain amount of energy. The energy required for the transition from a state of lower energy to a state of higher energy is directly related to the frequency of electromagnetic radiation that causes the transition.
Spectral Distribution of Radiant Energy

V' C V = Wave number (cm -1) = Wave length (nm) = Velocity of Radiation (constant) 3 1010 cm/sec = Frequency of Radiation (cycles/sec)
V 1
V' =
C
(The energy of photon) E = Vh (Planck's Constant 6.62 10-27 erg -sec ) E = Vh = h C = V

C C
1 x 107 erg = I joule =0.239 calorie Avogadros number = 6.02 x 10 23 mol-1
V =
Spectral Properties, Application and Interactions of Electromagnetic Radiation

Energy Electron volts, eV Wave Number V Wavelength Frequency Type Radiation Type spectroscopy Type Quantum Transition
Kcal/mol
cm-1
cm
Hz
9.4 x 107
4.9 x 106
3.3 x 1010
3 x 10-11
1021
Gamma ray X-ray Ultra violet Visible
Gamma ray emission X-ray absorption, emission UV absorption
Nuclear Electronic (inner shell)
9.4 x 103
4.9 x 102
3.3 x 106
3 x 10-7
1017
9.4 x 101
4.9 x 100
3.3 x 104
3 x 10-5
1015
Electronic (outer shell) Molecular vibration
9.4 x 10-1
4.9 x 10-2
3.3 x 102
3 x 10-3
1013
Infrared
IR absorption
Molecular rotation
9.4 x 10-3
4.9 x 10-4
3.3 x 100
3 x 10-1
1011
Microwave Radio
Microwave absorption Nuclear magnetic resonance Magnetically induced spin states
9.4 x 10-7
4.9 x 10-8
3.3 x 10-4
3 x 103
107
Molecular Orbital of Triplet Oxygen

Molecular Atomic
* 2Px 2Py 2Pz * * 2Pz 2Py 2Px
Atomic
Energy
* 2S 2S
* 1S 1S
Quantum Numbers and Orbitals

Principal quantum number (n): The average distance of the electron from the nucleus. 1, 2, and so on. Azimuthal quantum number (Momentum quantum number) (l): The shape of the orbital. 1s, 2s, 2p, 3s, 3p, 3d, etc Magnetic quantum number (Orientational quantum number) (ml): The orientation of orbital in the space. 2px 2p , 2pz x, y and z are orientational quantum number
y
Electron spin quantum number (ms)= The two possible orientation of the electron in a magnetic field. 1/2 or 1/2
One S and Three P Orbitals
The 5 d Orbitals
II. Ultra Violet Spectrometry
The absorption of ultraviolet radiation by molecules is dependent upon the electronic structure of the molecule. So the ultraviolet spectrum is called electronic spectrum.

Kcal/mol
cm-1
cm
Hz
9.4 x 107
4.9 x 106
3.3 x 1010
3 x 10-11
1021
9.4 x 103
4.9 x 102
3.3 x 106
3 x 10-7
1017
9.4 x 101
4.9 x 100
3.3 x 104
3 x 10-5
1015
9.4 x 10-1
4.9 x 10-2
3.3 x 102
3 x 10-3
1013
Infrared
IR absorption
Molecular rotation
9.4 x 10-3
4.9 x 10-4
3.3 x 100
3 x 10-1
1011
Microwave Radio
Microwave absorption Nuclear magnetic resonance Magnetically induced spin states
9.4 x 10-7
4.9 x 10-8
3.3 x 10-4
3 x 103
107
Electronic Excitation
The absorption of light energy by organic compounds in the visible and ultraviolet region involves the promotion of electrons in , , and n-orbitals from the ground state to higher energy states . This is also called Energy Transition. These higher energy states are molecular orbitals called antibonding.
Types of Bonds
* Antibonding Antibonding Nonbonding Bonding Bonding
Energy
n *
n *
Electronic Molecular Energy Levels
The higher energy transitions ( *) occur a shorter wavelength and the low energy transitions ( *, n *) occur at longer wavelength.
Electronic Ground and Excitation States
hv
Energy
* hv
hv
* hv n
* n
Chromophore
Chromophore is a functional group which absorbs a characteristic ultraviolet or visible region. 210 nm 233 nm 268 nm 315 nm Double Bonds Conjugated Diene Conjugated Triene Conjugated Tetraene
and * orbitals
and * orbitals
III. Infrared Spectrometry

Radiation energy in the infrared region is absorbed by the organic compound and converted into energy of molecular vibration. The energy absorption pattern thus obtained is commonly referred to as an infrared spectrum which has the plot of intensity of radiation absorption versus wavelength of absorption.

Kcal/mol
cm-1
cm
Hz
9.4 x 107
4.9 x 106
3.3 x 1010
3 x 10-11
1021
9.4 x 103
4.9 x 102
3.3 x 106
3 x 10-7
1017
9.4 x 10
4.9 x 10
3.3 x 10
3 x 10
-5
10
1 5
9.4 x 10-1
4.9 x 10-2
3.3 x 102
3 x 10-3
1013
Infrared
IR absorption
Molecular rotation
9.4 x 10-3
4.9 x 10-4
3.3 x 100
3 x 10-1
1011
Microwave Radio
Microwave absorption Nuclear magnetic resonance
9.4 x 10-7
4.9 x 10-8
3.3 x 10-4
3 x 103
107
Magnetically induced spin states
Some Molecular Vibrations

H H O Unsymmetrical bend
Symmetrical bend
C H Stretch
Atom, Group, and Molecular Rotations

Z H atom rotation H H CH 3 group rotation H C O H OH group rotation O Y COOH group rotation
Molecular rotation
Center of gravity of the molecule is at the origin
Infrared Spectrum
Infrared Absorption and Functional Groups
3.4 6.0 10.3 5.8 3.7 2.9
m m m m m m
Alkane cis-Double Bond trans-Double Bond Carbonyl Hydroxyl Stretching of Acid Group Hydroxyl

Identification of Compounds: Uv, Ir, NMR and Mass Spectrometries

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Identification of Compounds

by UV, IR, NMR AND MASS SPECTROMETRIES

Gas Chromatogram of Flavor Compounds

I. II. III. IV. V.

I. Introduction of Spectrometric Analyses

frequency, (cycles/sec) , yellow orange violet green visible region

600 700 Wavelength, nm ,

Spectral Distribution of Radiant Energy

(The energy of photon) E = Vh (Planck's Constant 6.62 10-27 erg -sec ) E = Vh = h C = V

1 x 107 erg = I joule =0.239 calorie Avogadros number = 6.02 x 10 23 mol-1

Spectral Properties, Application and Interactions of Electromagnetic Radiation

Gamma ray X-ray Ultra violet Visible

Gamma ray emission X-ray absorption, emission UV absorption

Nuclear Electronic (inner shell)

Electronic (outer shell) Molecular vibration

Microwave absorption Nuclear magnetic resonance Magnetically induced spin states

Molecular Orbital of Triplet Oxygen

Quantum Numbers and Orbitals

One S and Three P Orbitals

II. Ultra Violet Spectrometry

Spectral Properties, Application and Interactions of Electromagnetic Radiation

Gamma ray X-ray Ultra violet Visible

Gamma ray emission X-ray absorption, emission UV absorption

Nuclear Electronic (inner shell)

Electronic (outer shell) Molecular vibration

Microwave absorption Nuclear magnetic resonance Magnetically induced spin states

Electronic Molecular Energy Levels

Electronic Ground and Excitation States

III. Infrared Spectrometry

Spectral Properties, Application and Interactions of Electromagnetic Radiation

Gamma ray X-ray Ultra violet Visible

Gamma ray emission X-ray absorption, emission UV absorption

Nuclear Electronic (inner shell)

Electronic (outer shell) Molecular vibration

Microwave absorption Nuclear magnetic resonance

Magnetically induced spin states

Some Molecular Vibrations

Atom, Group, and Molecular Rotations

Center of gravity of the molecule is at the origin

Infrared Absorption and Functional Groups

3.4 6.0 10.3 5.8 3.7 2.9

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