mch-401:application of spectroscopy (organic) unit- 4th: carbon-13 nmr … 13 nmr.pdf ·...
TRANSCRIPT
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MCH-401:Application of Spectroscopy (Organic)
UNIT- 4th: Carbon-13 NMR Spectroscopy
Prof.Anand HalveS.O.S in ChemistryJiwaji University Gwalior
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C. NMR Spectroscopy
1. General Theory
2. 13C NMR
3. 1H NMR
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1. General Theory of NMR
A magnetic field is generated by a spinning charge
The nucleus of many atoms is a spinning charge.
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For many nuclei, an external magnetic field will cause
the spinning charge to either line up with
the external magnetic field or against it
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The β spin state is slightly greater in energy.
The difference in energy between α and β increases
with increasing magnetic field strength.
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Nuclei can absorb energy.
When nuclei in the α state absorb radiation
equal in E to the difference between the α
and β spin states, the α spin state is
promoted to the β spin state.
The radiation required for “spin flipping”
has a frequency in the radio wave range
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Nuclei can emit energy.
As nuclei move from
the β spin state to the α spin state,
energy is emitted and the frequency of that
energy can be detected.
resonance = nuclei flipping back and forth
between the α and β spin state.
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Resonance is the “Song of the Nuclei.”
Every molecule sings its own song
as a result of its structure.
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Analysis of an NMR spectrum
may involve analyzing:
a) The number of signals a molecule emits
b) The frequencies at which signals occur
c) The intensity of signals
d) The splitting of signals
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2. 13C NMR
a) Number of signals
b) Position of signals
c) DEPT data
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a) The number of signals correlates
with the number
types of carbon
in a molecule
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cyclopentane
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13C-NMR cyclopentane
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Pentane
CH3CH2CH2CH2CH3
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13C-NMR pentane
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13C-NMR hexane
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13C-heptane
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13C-NMR chlorocyclopentane
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13C-NMR 2,2-dimethylpropanal
O
C
H
CH3
C CH3
CH3
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13C-NMR 2-methylbutane
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13C-NMR toluene
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(Z)-3-methyl-2-pentene
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(E)-3-methyl-2-pentene
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Consider C4H9Br
Which isomers are represented by
these spectra?
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b) The positions of signals
correlate with the extent of
shielding and deshielding
by electrons
experienced by each C nucleus
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Diamagnetic Shielding
The greater the electron density
around a C nucleus, the lower
the effective magnetic field
around that C nucleus.
Needs lower frequency for
resonance
The carbon nucleus is
“shielded”
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Carbon nuclei adjacent to
electronegative atoms experience a lower
e- cloud density
These carbons are “deshielded”
and require greater frequencies for
resonance.
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carbons carbons
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Chemical Shift
The frequency at which a nucleus will resonate isdependent on the magnetic field strength.
Because this can vary from instrument toinstrument, frequency is expressed relative tomagnetic field strength, “chemical shift”
Chemical Shift = frequency of resonance (Hz)
frequency of instrument(MHz)
units = parts per million = ppm
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13C Chemical Shift Correlation Chart
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pentane
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hexane
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cyclopentane
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ethyl bromide
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n-propyl chloride
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ethanol
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2-propanol
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O
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ethyl propyl ether
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Ethyl amine
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Acetaldehyde
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2,2-dimethylpropanal
O
C
H
CH3
C CH3
CH3
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Acetone
O
CH3C CH3
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2-pentanone
O
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acetic acid
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Propionic acid
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methyl propionate
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Acetamide
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N-methyl acetamide
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1-pentene
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(Z)-3-methyl-2-pentene
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(E)-3-methyl-2-pentene
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2-butyne
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Benzene
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toluene
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Benzaldehyde
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c) DEPT data
DEPT = distortionless enhancement by polarization
Distinguishes:
CH3 - methyl groups
-CH2- methylene groups
I-CH- methine groups
I-C- 4o carbons ( not detected by DEPT)
I
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DEPT 13C spectrum of citronella
C10H16O
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C4H10O
CH3
4o C
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C4H10O
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C4H10O
CH3
4o C
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C5H10O
CH2
CH3
4oC
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C5H10O
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C5H10O
CH2
CH3
4oC
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C4H8O2
CH2
CH34o C CH3
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C4H8O2
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C4H8O2
CH2
CH34o C CH3
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C8H9Br
Both CH
CH2
4o C 4oC
CH3
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C8H9Br
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C8H9Br
CH CH
CH2 CH3
4o C 4o C
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Both C3H6O2
CH2
4oC
A
4oC
CH3
CH3
CH2
B
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A
B
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C3H6O2
CH2
4oC
A
4oC
CH3
CH3
CH2
B
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1H NMR
CH3COCH2OH CH3CH2COOH