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Overview on Edible Vaccine: Pros & Cons with Mechanism
13CNMRfor322.pdf
1. 13C-NMR
We can examine the nuclear magnetic properties of carbon
atoms in a molecule to learn about a molecules structure.
Most carbons are 12C; 12C has an even number of protons
and neutrons and cannot be observed by NMR techniques.
Only 1% of carbons are 13C, and these we can see in the
NMR.
This makes 13C-NMR much less senstive than carbon NMR.
This affects the how we see splitting patterns.
2. A 13C-NMR spectrum.
RF
absorbance
RF Frequency
Here is what’s cool about 13C-NMR:
Different carbons appear at different
frequencies! - Now you know how
many different types of Carbons you
have!
The intensity of the peak doesn’t does not necessarily
correlate to the number of carbons.
An internal
standard
called
TMS is
used to set
the scale to
zero
3. Example: Two alcohols (-OH compound) with formula C3H8O
1. IHD = 0
2. Possible structures:
O
H
O
H
O
CH3
C
H2
H2
C
O
H
Same!
4. O
H
These two carbons
are identical by
symmetry:
The C-NMR
spectrum of
isopropanol
only shows
two different
carbons!
7. An isolated 13C atoms have the same chemical shift. (resonate at
the same frequency)
C
Nucleus
Electron “cloud”
The electron cloud of the atom partially shields the nucleus from the
surrounding magnetic field
When the carbon nucleus is adjacent to an electronegative atom, the
carbon nuclei has fewer Electrons around it.
C F
Nuclei with less electron density around them will resonate at a different
frequency: It requires shorter wavelength radio waves (or a weaker magnetic
field) to cause a carbon nuclei to resonate if it has less electron density around it.
8. C O
C C
C C
C
0
50
100
150
200
40 -5
sp3
90 70
sp
150 105
sp2
150 120
aromatic
210 160
carbonyl
Typical Values of Chemical shift depend on the
1. Hybridization
2. Electronegativity of attached atom(s).
C O
C Br, (Cl)
75 50
Some specific values are included in tables Section IV your text book!
9. Conversely atoms that donate electron density cause nuclei to resonate at
lower frequencies (higher field strengths).
Si
CH3
CH3
CH3
CH3
The silicon in tetramethylsilane (TMS)
shields the carbon nuclei and makes them
appear “up-field”
The chemical shift spectrum is
measured relative to TMS.
TMS
Shift
10. TMS
Shift
δ= is used to signify chemical shift.
Because the frequency depends on
the field strength,
one uses a relative units scale of
“parts per million” or ppm
Chemical shifts reported as ppm units give the same values
for the same compound regardless of the instrument used!
δ = (v(compound)- v(TMS))/ v(TMS)
THE δ SCALE IS USED TO MEASURE CHEMICAL SHIFT
15. 13C peaks are in reality split by bonded protons.
Generally
shown like this:
Actually looks
like this:
H
C
Why??
C H
Adjacent nuclear spin of the proton locally increases
magnetic field felt by carbon nuclei.
Carbons next to
up proton spin
Carbons next to
down proton spin
NOTE: There are only
two possible peaks for
C’s having one adjacent
proton.
or
A “doublet”
16. H
C
H
H
Appears as quartet.
There are eight possibilities:
The general rule is:
The number of peaks observed is equal to the number of attached
protons, (N), plus one.
Splitting = N+1
FOR 13C it is the number of protons directly
attached to the carbon that cause splitting.
17. PAY ATTENTION!:
13C-NMR 1H-NMR
C C
H
H
H
C
H
H
Splitting pattern reflects how
many protons are directly
attached to the carbon atom
A Triplett
Splitting pattern reflects how
many protons are connected
to adjacent carbon atom(s)
A doublet
A Triplett
C C
H
H
H
The chances that
my neighbor is also a
C-13 is 1/100
there is a 99%
chance that the
attached “H” has a
spin
19. Why don’t the spins on
adjacent Carbons split each
C C
Only 1% of Carbons have a spin! (Most are 12C and are
NMR inactive).
Therefore only 1 in ten thousand pairs of Cs have both have
spin and are coupled. That’s too small to detect!
20. Protons can couple (cause splitting) of C-13 peaks but we
“don’t see” splitting of proton peaks by carbon!!
C-H splitting is very small because only 1% of Carbon has a
spin!.
C-13 satellites
You can see carbon-proton
coupling if you look very closely!
21. Note all of these split peaks can quickly get confusing:
Am I looking at two different carbon resonances or a single doublet?
For this reason we show our spectra without splitting. But we often see
the splitting indicated over the peak:
26. It is helpful to know what typical values of unfunctinalized C’s
Approximate Chemical Shifts ranges for unsubstituted Alkanes
5-22 ppm
15-33 ppm
25-35ppm
C=C 110-150ppm
66-90ppm
R C
H
H
H
R C
R
H
H
R C
R
R
H R C
R
R
R
C C
27. If your molecules containing Oxygen:
O
C
R H
O
C
R R
O
C
R O
O
C
R NHR
R = alkyl
O
C
R X
X = Cl, Br, I
195 - 220
doublet
195 - 220
but singlet!
165-180 165-180 165-180
O
C
H3C O
O
C
H3C N
H
60.4 34.4
O
C
O O
~155
C O
H
C O C
50 - 75 ppm 50 - 75ppm
(Similar to alcohol
but two of them!)
C
O O
90 - 100 ppm
28. If your molecule contains Nitrogen:
C NH2
28-47 ppm
C
N
C
H
C
N
C
C
Amines:
C N
O
O
61 - 85 ppm
Nitro-
C
N
R
Imine
~155 ppm
C N
C
14-30
~120
34. How do you take an NMR??
+ -
N S
RF
transmitter
RF
Receiver
Energy
No Field Magnetic Field
Stronger
Magnetic Field
I. Constant Radio frequency but change magnetic
field
! OLD TRADITIONAL WAY!
DOWN
FIELD
UP
FIELD
Know these terms!!
Max Tofield Rogers 1956
de-shielded shielded
35. Modern NMR spectra are obtained
at constant field strength
CONSTANT MAGNETIC FIELD!--Change Frequency
No Absorbtion
not enough
energy
Absorbtion
Energies Match!
No Absorbtion
Energy too high
36. RF-Pulse
Technically speaking: you don’t
selectively excite all the nuclei but
rather you saturate the exchange
of nuclei between the upper an
lower energy states. At
equilibrium (in the absence of the
RF energy) there are slightly
more nuclei in the lower energy
state than in the upper energy
state based on the normal
Boltzman distributions.
ENERGY
RF-Pulse
FT-NMR
different RF
frequencies
13C
FYI
37. Consider the population of like-nuclei in a sample:
Should be more
in the ground state!
Irradiate
wait
hv
FYI
38. hv
Spin is conserved:
When a nuclei changes spin,
some other particle in the
universe must also change spin.
The coupling of spin is more efficient the
closer the two particles are and if they are
connected by bonds.
FYI
40. DEPT (JVERT): APT (Attached Proton Test) experiment is not as sensitive as a DEPT experiment, the APT has the advantage of seeing all
carbons present: CH0 at 145 ppm and CH2 at 29 ppm are negative, while CH3 at 16 ppm and CH in the range of 126-129 ppm are positive. Thus
Cc and Cb are negative, while Ca, Cd, Ce, and Cf are positive.Spectrum of Ethyl Benzene:
C
CH2
CH
CH3
FYI