2. THIS IS A VAST TOPIC AND A SHORT
OVERVIEW IS GIVEN
AND
IN NO WAY COMPLETE JUSTICE CAN BE
DONE FOR THIS
3. DEFINITION
NMR is a phenomenon exhibited by when
atomic nuclei in a static magnetic field absorbs
energy from radiofrequency field of certain
characteristic frequency.
It results to give a spectrum with frequency on x-
axis and intensity of absorption on y-axis.
4. NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY
Proton (1H) and carbon (13C) are the most important nuclear
spins to organic chemists
Nuclear spins are oriented randomly= absence (a) of an
external magnetic field.
specific orientation= presence (b) of an external field, B0
Pavia, Lampman, Kriz, Vyvyan; Spectroscopy, Cengage Learning, India edition,
2007, Pg. no. 108
5. NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY
Some nuclear spins are aligned parallel to the external field
Lower energy orientation
Some nuclear spins are aligned antiparallel to the external
field
Higher energy orientation
P.S.Kalsi; Spectroscopy Of Organic Compounds, Sixth Edition:2004, Page no.-195
6. INTRODUCTION
Nuclear magnetic resonance concern the magnetic properties of
certain atomic nuclei. It concerns the atoms having spin quantum
number.
12C nucleus is not magnetically active the spin number I being
zero. But 13C Have I = ½
13C account for only 1.1% of naturally occurring carbon 13C- 13C
coupling is negligible and not observed.
The gyromagnetic ratio of 13C is one-fourth of that of 1H.
Each nonequivalent 13C gives a different signal.
A 13C signal is split by the 1H bonded to it according to the (n + 1)
rule.
The most common mode of operation of a 13C-NMR spectrometer
is a hydrogen-decoupled mode.
7. PRINCIPLE & THEORY
The nuclear magnetic resonance occurs when nuclei aligned with
an applied field are induced to absorb energy and change their spin
orientation with respect to the applied field.
The energy absorption is a quantized process, and energy
absorbed must equal the energy difference between the two states
involved.
E absorbed = (E-1/2state- E+1/2state) =hv
The stronger the applied magnetic field, greater the energy
difference between the possible spin states.
ΔE = ∫(B0)
8. PRINCIPLE OF NMR
When energy in the form of radiofrequency is applied
When applied frequency is equal to precessional
frequency.
Absorption of energy occures
Nucleus is in resonance
NMR signal is recorded.
Pavia, Lampman, Kriz, Vyvyan; Spectroscopy, Cengage Learning, India edition,
2007, Pg. no. 108
9. NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY
Many nuclei exhibit NMR phenomenon
All nuclei with odd number
of protons
All nuclei with odd number
of neutrons
Nuclei with even numbers
of both protons and neutrons
do not exhibit NMR
phenomenon
Table-1
10.
11. ABUNDANCE
13C is difficult to record because of
1. The most abundant isotope of carbon that is
12C (99.1%) is not detected by nmr because it
has an even no of protons and neutrons 12C is
nmr inactive.
2. Magnetic resonance of 13C is much weaker.
Moreover, gyromagnectic ratio of 13C being only
one fourth that of proton, so the resonance
frequency of 13C is one fourth that of proton nmr.
12.
13. Advantages of 13C- NMR over 1H- NMR
1. 13C- provides information about the backbone of
molecules rather than the periphery.
2. The chemical shifts range for 13C- NMR for most organic
compounds is 200 ppm compared to 10 –15 ppm for H, hence there is
less overlap of peaks for 13C- NMR.
3. Homonuclear spin-spin coupling between carbon atoms is not
observed because the natural abundance of 13C is too low for two 13C to
be next to one another.
Heteronuclear spin coupling between 13C and 12C does not occur
because the spin quantum number of 12C is zero.
4. There are a number of excellent methods for decoupling the
interaction between 13 C and 1H.
14. SPIN –SPIN SPLITTING OF 13C
SIGNALS
Splitting take place acc. to 2nI+1 rule
Where n= no. of nuclei
I=spin quantum number
CH3 = 3+1=4 quartet
CH2 = 2+1=3 triplet
CH = 1+1=2 doublet
C = 0+1=1 singlet
CDCl3 gives three peaks because its I=1 so acc. to 2nI+1
2×1×1+1=3 so it gives 1:1:1 peaks
Solvents used are CDCl3, DMSO, d6acetone, d6 benzene
15. 13C chemical shifts
The most significant factors affecting the chemical shifts are:
Electro negativity of the groups attached to the C
Hybridization of C
The intensity (size) of each peak is NOT directly related to the
number of that type of carbon. Other factors contribute to the size
of a peak:
Peaks from carbon atoms that have attached hydrogen atoms are bigger than
those that don’t have hydrogens attached.
Carbon chemical shifts are usually reported as downfield from the
carbon signal of tetramethylsilane (TMS).
16. Why Carbon-13 NMR required?
Carbon NMR can used to determine the number of non-equivalent
carbons and to identify the types of carbon atoms(methyl, methylene,
aromatic, carbonyl….) which may present in compound.
13C signals are spread over a much wider range than 1H signals making
it easier to identify & count individual nuclei.
17. WHY 13C NMR REQUIRED ??
Proton NMR used for study of number of nonequivalent
proton present in unknown compound.
Carbon NMR can used to determine the number of non-
equivalent carbons and to identify the types of carbon
atoms(methyl, methylene, aromatic, carbonyl….) which may
present in compound.
13C signals are spread over a much wider range than 1H
signals making it easier to identify & count individual nuclei.
18. CHARACTERISTIC FEATURES OF 13C NMR
• The chemical shift of the CMR is wider(δ is 0-220 ppm relative to TMS) in
comparison to PMR(δ is 0-12ppm relative to TMS).
• 13C-13C coupling is negligible because of low natural abundance of 13C in
the compound.
• Thus in one type of CMR spectrum(proton de coupled) each magnetically
non equivalent carbon gives a single sharp peak that does undergo further
splitting.
19. CHARACTERISTIC FEATURES OF 13C NMR
The area under the peak in CMR spectrum is not necessary
to be proportional to the number of carbon responsible for
the signal. Therefore not necessary to consider the area
under ratio.
Proton coupled spectra the signal for each carbon or a
group of magnetically equivalent carbon is split by proton
bonded directly to that carbon & the n+1 rule is follwed.
13C nucleus is about one-fourth the frequency required to
observe proton resonance.
The chemical shift is greater for 13C atom than for proton
due to direct attachment of the electronegative atom to 13C
Gurdeep R. Chatwal, Sham K.Anand; Instrumental Methods Of Chemical Analysis,
Enlarge edition 2002,Pg. no. 2.31-2.32
20. 13C CHEMICAL SHIFTS
are measured in ppm (d) from the carbons of TMS
• The correlation chart is here divided into sections
1) the saturated carbon atom which appear at Upfield,nearest to TMS(8-
60ppm).
2) effect of electronegative atom(40-80ppm)
3) Alkenes and aromatic carbon atom(100-170)
4) It contain carbonyl carbon bond. which appear at Downfield value(155-
200ppm).
Pavia, Lampman, Kriz, Vyvyan; Spectroscopy, Cengage Learning, India edition,
2007, Pg. no. 177
21.
22. 13C INTERPRETATION
Count how many lines- how many types of carbons
Symmetry duplicates give same line- if there are more
carbons in your spectrum – symmetry
Check chemical shift window-
Check splitting pattern-
Signal height size-?
23. 13C INTERPRETATION
13C NMR spectroscopy provides information
about:
The number of nonequivalent carbons atoms in
a molecule
The electronic environment of each carbon
How many protons are bonded to each carbon
24.
25.
26.
27. EXAMPLE
PREDICTING CHEMICAL SHIFTS IN 13C NMR SPECTRA
Solution
Ethyl acrylate has five distinct carbons: two different C=C,
one C=O, one C(O)-C, and one alkyl C. From Correlation
chart the likely absorptions are
28.
29. CHEMICAL SHIFT
Carbon-13 chemical shifts are most affected by,
Hybridiasation state of carbon & Electronegative group attached to carbon.
35. 1H AND 13C NMR COMPARED
13C signals are spread over a much wider range than 1H
signals making it easier to identify and count individual
nuclei
Figure #1 shows the 1H NMR spectrum of 1-chloropentane;
Figure #2 shows the 13C spectrum. It is much easier to identify
the compound as 1-chloropentane by its 13C spectrum than
by its 1H spectrum.
37. 1-CHLOROPENTANE
Chemical shift (d, ppm)
ClCH2CH2CH2CH2CH3
020406080100120140160180200
13C
CDCl3
a separate, distinct
peak appears for
each of the 5
carbons
38. 13C CHEMICAL SHIFTS ARE MOST AFFECTED BY
hybridization state of carbon-
electronegativity of groups attached to
carbon-
Pavia, Lampman, Kriz, Vyvyan; Spectroscopy, Cengage Learning, India edition,
2007, Pg. no. 176-178
Easy use
chart
39. PREDICTING 13C SPECTRA
CH3 CH3
C C
C
C
C
CH3
plane of symmetry
4 lines
O
CH3
CH3
O
CH3
CH3
C
C
c
CH3
O
CH3 5 lines
CH3
C
CH3
C
CH3
H
5 lines
40. PREDICTING 13C SPECTRA
CH3
CH3
H3C CH3
C C
C
CC
C
H3C CH3
4 lines
C C
CH3
CH3
CH3
CH3
C C
CH3
CH3
CH3
CH3
2 lines
Symmetry Simplifies Spectra!!!
42. PROBLEMS OF 13
C
• Natural abundance-
13
C natural abundance is very low (1.1%).
Gyro magnetic ratio-
13
C nucleus gyro magnetic ratio is much
lesser than proton nucleus. 13
C-1.404; 1
H-5.585.
Coupling phenomenon-
13
C & 1
H have I=1/2 so that coupling
between them probably occur.
Y.R.Sharma,S.Chand; Elementary Organic Spectroscopy, India edition, 2009,Pg.
no. 71
43. PROBLEMS IN NMR CAN BE OVERCOME BY
Fourier Transform Technique-
Decoupling Technique-
1) Broad Band Decoupling
2) Off Resonance Decoupling
3) DEPT (Pulse) Decoupling
Nuclear Overhauser Phenomenon-
44. SIGNAL AVERAGING AND FT-NMR
Low abundance of 13C is overcome by signal averaging and
Fourier-transform NMR (FT-NMR)
Signal averaging
Numerous individual runs are added together and
averaged such that random background noise cancels to
zero and NMR signals are enhanced, substantially
increasing sensitivity.
45. SIGNAL AVERAGING AND FT-NMR
FT-NMR: (Pulse FT_NMR)
Sample is irradiated with entire range of useful frequencies
13C nuclei in the sample resonate at once giving complex,
composite signal that is mathematically manipulated by Fourier
transforms to segregate individual signals & convert them to
frequencies.
Advantages-
More sensitive-
Very fast-
Pavia, Lampman, Kriz, Vyvyan; Spectroscopy, Cengage Learning, India edition,
2007, Pg. no. 121
46. Carbon-13 NMR spectra of pentan-1-ol. Spectrum (a) is a single run,
showing background noise. Spectrum (b) is an average of 200 runs
Signal Averaging and FT-NMR, Pentan-1-ol
47. 13
C-NMR SPIN-SPIN COUPLING
1
H NMR: Splitting reveals number of H neighbours.
13
C NMR: Limited to nuclei separated by just one sigma
bond; no Pi bond.
1
H
13
C
13
C
12
C
Coupling observed
Coupling occurs but signal
very weak, low probability
For two adjacent 13
C
1.1% X 1.1% = 0.012%
No Coupling
No Coupling.
48. DECOUPLING TECHNIQUES
• Irradiation of all 1H nuclei by using
decoupler
• 1H nuclei are saturated & C nuclei see
zero coupling
Proton or Noise
Decoupling
• Provides multiplet information keeping the
spectrum simple.
• Coupling between C & H attached directly
to it
off Resonance
Decoupling
• Involves complex program of pulse &
delay times in C & H channel
• C atoms attached to varying no. of H
exhibit different phases
DEPT
49. PROTON OR BROADBAND DECOUPLING
a sample is irradiated with two different radiofrequencies.
,
These rapid transition decoupled any spin-spin interaction
between 1H & 13C nuclei.
Due to rapid change, all spin interactions are averaged to
zero.
Appear only 13C spectrum
Disadvantage.-information on attached H is lost.
Pavia, Lampman, Kriz, Vyvyan; Spectroscopy, Cengage Learning, India edition,
2007, Pg. no. 181
1-to excite all C
nuclei
2-to cause all protons
-rapid transition
52. Broad band decoupling
1. It avoid spin-spin splitting of 13C lines by 1H
nuclei.
2. In this, all the protons are simultaneously irradiated with a
broad band radiofrequency signal. Irradiation causes the protons
to become saturated and they undergo rapid upward downward
transition among all their possible spin state. This is produced
by a second coil located in the sample probe.
3. Without decoupling 13C spectra would show complex overlapping
multiplets that would be hard to interpret.
4. The spin-spin information get lost, but we can use off-resonance
decoupling to get spin-spin
shifts back
53. 13C OFF-RESONANCE DECOUPLING
In this technique the 13C nuclei are split only by the protons
directly bonded to them as a result the multiplets become
narrow & not removed altogether as in fully decoupled
spectra.
It simplifies the spectrum by allowing some of the splitting
information to be retained.
The N + 1 rule applies: a carbon with N number of protons
gives a signal with N + 1 peaks.
P.S.Kalsi; Spectroscopy Of Organic Compounds, Sixth Edition:2004, Page no.-377
55. OFF-RESONANCE DECOUPLING
Off-Resonance decoupling simplifies the spectrum by
allowing some of the splitting information to be retained.
In this technique only the 13C nuclei are split by the protons
directly bounded to them and not by any other protons i.e.,
one observes only one bond coupling 13C -1H
The coupling between each carbon atom and each
hydrogen attached directly to it, n+1 rule.
Use of off-resonance decoupled spectra has been replaced
by use of DEPT 13C NMR
58. Nuclear Overhauser Enhancement (NOE)
A. Under conditions of broad band decoupling it found that the area of the 13C
peaks are enhanced by a factor that is significantly greater than that which is
expected from the collapse of multiplets into single lines.
B. This is a manifestation of nuclear overhauser enhancement.
C. Arises from direct magnetic coupling between a decoupled proton and a
neighboring 13C nucleus that results in an increase in the population of the lower
energy state of the 13C nucleus than that predicted by the Boltzmann relation.
D. 13C signal may be enhanced by as much as a factor of 3 x
E. Disadvantage –
1. Lose the proportionality between peak areas and the number of nuclei of that
type of 13C.
59. THEORY OF NOE
Consider a hypothetical
molecule in which 2 protons
are in close proximity . In such
compound, if we double
irradiate Hb,then this proton
gets stimulated and the
stimulation is transferred
through space to the relaxation
mechanism of Ha.
C C
Ha Hb
59
Thus, due to increase in spin lattice relaxation
of Ha, its signal will appear more intense by 15
to 50%. So, if the intensity of absorption of Ha
signal is increased by double irradiating Hb,
then protons Ha and Hb must be in close
proximity in a molecule
60. Off-resonance decoupling
1. The coupling between each carbon atom and each hydrogen
attached directly to it, s observed acc to n+1 rule.
2. Apparent magnitude of the coupling constant is reduced and
overlap of the resulting multiplets is less frequent
3. Set decoupling frequency at 1000 to 2000 Hz above
the proton spectral region which leads to a partial
decoupled spectrum in which all but the largest spin spin
shifts are absent.
61. HYDROGEN DECOUPLED
MODE(BROAD BAND DECOUPLED)
A sample is irradiated with two different radio frequencies.
One to excite all 13C nuclei.
A second broad spectrum of frequencies to cause all
hydrogen's in the molecule to undergo rapid transitions
between their nuclear spin states.
On the time scale of a 13C-NMR spectrum, each hydrogen is in an
average or effectively constant nuclear spin state, with the result
that 1H-13C spin-spin interactions are not observed; they are
decoupled.
Thus, each different kind of carbon gives a single, unsplit peak.
65. 25 MHz 13C NMR spectra of diphenyl selenide in CDCl3.
Figure shows the fully coupled and decoupled 13C NMR spectra of diphenyl
selenide.
Although the large 1JC-H splittings are easy to identify, the fine structure of the
individual multiplets is not first order (e.g., only the para carbon has an
approximately centrosymmetric pattern, the others do not).
This is because we are looking at the X part of an AA'BB'CX pattern (ABC are
protons, X is carbon). Since the AA' and BB' parts are strongly coupled, we
see the usual complex effects of "virtual coupling" on the X resonance . When
noise {1H} decoupling is applied, the spectrum becomes much more intense,
and only 4 lines remain, one for each carbon.
In this compound we have a second magnetically active nucleus (77Se,
natural abundance 7.5%, I = 1/2), so each of the 13C peaks has 77Se satellites,
although coupling between C-4 and the selenium is too small to detect (the
satellites are under the main peak).
66. Most 13C NMR spectra are very complex. The methyl carbon of an
ethoxy group will appear as a large quartet, with each line further split
into triplets.
Even in fairly simple molecules each carbon may be coupled to a
number of different protons. In complicated molecules, these multiplets
overlap badly, and may be impossible to analyze.
1JCH = 100-250 Hz
2,3JCH = 2-10 Hz
To simplify 13C spectra, we usually use some form of broadband
decoupling (noise decoupling) to remove the effect of proton couplings.
This also dramatically increases signal intensity, since now all carbons
appear as singlets (assuming absence of other spin 1/2 nuclei like 31P or
19F).
The increase is actually greater by a factor of 2-3 than would be
predicted on the basis of simply combining the 13C multiplet intensities
because the Nuclear Overhauser Effect causes additional increases in
67. DEPT 13C NMR Spectroscopy
Distortionless Enhancement by Polarization Transfer (DEPT-NMR)
experiment
• Run in three stages
1. Ordinary broadband-decoupled spectrum
• Locates chemical shifts of all carbons
2. DEPT-90
• Only signals due to CH carbons appear
3. DEPT-135
• CH3 and CH resonances appear positive
• CH2 signals appear as negative signals (below the baseline)
• Used to determine number of hydrogens attached to each carbon
68.
69.
70.
71. Attached proton test spectra
Another useful way of determining how many protons a
carbon in a molecule is bonded to is to use an attached
proton test (APT), which distinguishes between carbon
atoms with even or odd number of attached hydrogens.
A proper spin-echo sequence is able to distinguish
between S, I2S and I1S, I3S spin systems: the first will
appear as positive peaks in the spectrum, while the latter
as negative peaks (pointing downwards), while retaining
relative simplicity in the spectrum since it is still broadband
proton decoupled.
Even though this technique does not distinguish fully
between CHn groups, it is so easy and reliable that it is
frequently employed as a first attempt to assign peaks in
the spectrum and elucidate the structure
72. Spectral Editing
There are a number of multipulse experiments which render the signals
in a 13C NMR spectrum with positive and negative intensities
(sometimes zero) according to the number of attached protons.
J-Modulated Spectra. This is the most primitive form of spectral
editing. By placing a suitable delay time between the pulse and the
beginning of the acquisition, spectra are obtained in which C and CH2
groups are positive, and CH and CH3 are negative.
In this experiment, after the pulse there is a short delay, during which
the decoupler is turned off, and the 13C NMR spectrum becomes
modulated by the CH coupling frequency.
After the delay the decoupler is turned on, and the FID is recorded. If
the delay is 1/J then the quaternary and CH2 carbons are positive, and
the CH and CH3 signals are negative. If the delay is 1/2J all peaks
except quaternary are nulled
73. DEPT 13C NMR Spectroscopy
DEPT 45 ALL H BEARING PEAKS
74. DEPT 13C NMR Spectroscopy
(a) Ordinary broadband-decoupled
spectrum showing signals for all
eight of 6-methylhept-5-en-2-ol
(b) DEPT-90 spectrum showing
signals only for the two C-H
carbons
(c) DEPT-135 spectrum showing
positive signals for the two CH
carbons and the three CH3
carbons and negative signals for
the two CH2 carbons
SEE NEXT SLIDE
76. DEPT spectra of isopentyl acetate
CH3, CH
CH2
CH
DEPT spectra of isopentyl acetate
DEPT 45 ALL H BEARING PEAKS
POSITIVE
77. COSY SPECTRUM
2D NMR spectra have two frequency axes and one intensity
The common 2D spectra are 1 H -1H shift correlations known
as COSY Spectrum.
COSY identifies pair of protons which are coupled to each
other.
The compound is identified using a contour plot
One dimensional counterpart of a given peak on the
diagonal lies directly below that peak on each axis
The presence of cross peak normally indicates protons
giving the connected resonance on the diagonal are
geminaly or vicinally coupled.
JUST FOR A VIEW
79. HECTOR SPECTRUM
2D-NMR spectra that displays 13C – 1H-NMR shift correlations are called HETCOR
spectra. It shows coupling between protons and the carbon to which they are
attached. The HETCOR spectrum of 1-chloro-2propanol is shown in the fig.
The 2-D spectrum is composed only of cross-peaks, each one relating carbon to its
directly bonded proton(s).
The methyl doublet of 1H-NMR spectrum appears at δ 1.2 when drawn cross-peak
and then dropped down to the 13C spectrum axis indicates that the 13C peak at δ 20
is produced by the methyl carbon of 1-chloro-2-propanol(C-3)
The 1H -NMR signal at δ 3.9 is due to CH-OH (C-2 proton) tracing out to the
correlation peak and down to the 13C spectrum shows the 13C NMR signal at 67
arises from the C-2 carbon of the compound i.e., the carbon carrying the hydroxyl
group.
The 1H-NMR peaks at δ 3.4-3.5 for the two protons on the carbon bearing the
chlorine, the interpretation leads us to the cross-peak and down to the 13C peak at δ
51
80. THE HETCOR SPECTRUM OF 2-METHYL-3-PENTANONE
HETCOR: Heteronuclear Chemical Shift Correlation
indicates coupling between protons and the carbon to
which they are attached
81. APPLICATIONS OF 13C NMR
CMR is a noninvasive and nondestructive
method,i.e,especially used in repetitive In-vivo analysis of
the sample without harming the tissues .
CMR, chemical shift range(0-240 ppm) is wider compared to
H-NMR(0-14 ppm), which permits easy separation and
identification of chemically closely related metabolites.
C-13 enrichment, which the signal intensities and helps in
tracing the cellular metabolism.
CMR technique is used for quantification of drugs purity to
determination of the composition of high molecular weight
synthetic polymers.
82. Application’s
• C-13 enrichment, which the signal intensities and helps in tracing
the cellular metabolism.
• C13 nuclei are a stable isotope and hence it is not subjected to
dangers related to radiotracers.
• .CMR technique is used for quantification of drug purity to
determination of the composition of high molecular weight
synthetic polymers.
103. 103
S
N
N
S
N
O
Cl
H3C
4d
Molecular Formula = C20H16ClN3OS2
C=O
CH3
CH-Cl
CH
13C NMR spectrum of 3-chloro-1-[5-(4-methylphenyl)[1,3]thiazolo[4,3-b][1,3,4]thiadiazol-2-yl]-4-
phenylazetidin-2-one (4d)
114. d (ppm) type of signal in DEPT represent
22 (b) positive 2 CH3
24 (c) positive CH3
24 (a) positive CH
37 (d) negative CH2
62 (e) negative CH2
170 (f) not present C of >C=O
Interpretation :
127. The 13C NMR (APT, 50 MHz, DMSO-d6) study of the compound MIC-14
showed thirteen chemical shifts. Of these, seven were assigned to the
quaternary carbons, two to the primary aliphatic carbons and four to the
aromatic tertiary carbons. The carbons of the mesoionic ring of MIC-14 have
chemical shifts in 152.1; 141.4 and 161.9 ppm assigned, respectively, to C2,
C4 e C5 .The carbons C10 and C15 have chemical shifts of 40.6 and 21.4
ppm, while the aromatic carbons have chemical shifts of 132.7 (C6); 129.4 (C7,
7'); 123.8 (C8, 8'); 148.5(C9); 129.6 (C11); 129.8 (C12, 12'); 128.2 (C13, 13')
and 139.1 (C14).
http://dx.doi.org/10.1590/S0103-50532010000500024
128. For compound MIC-16 we observed a similar chemical behavior.
The 13C NMR (APT, 50 MHz, DMSO-d6) spectrum showed thirteen signals.
The carbons of the mesoionic ring showed chemical shifts of 148.7; 142.5 and
162.5 for C2, C4 and C5, respectively (see Carbons C10 and C15 show values
of chemical shifts that are compatible with the N-methyl group in 40.8 and the
methoxy group in 55.2.
The aromatic carbons have chemical shifts of 132.6 (C6); 130.4 (C7, 7'); 124.6
(C8, 8'); 148.5 (C9); 121.3 (C11); 132.6 (C12, 12'); 114.3 (C13, 13') and 160.4
(C14).
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132. MY BLOGS
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