The Two-Dimensional H,H-COSY highlighting the distinct correlations of two spin systems within the molecule
1H NMR NICOTINE
13 C NMR
DEPT90
DEPT135
1H 13C HSQC
HH TOCSY
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Structure and properties of Nicotine
1 - Structure of the molecule
Nicotine is also called 3-(1-methyl-2-pyrrolidinyl)pyridine according to the IUPACa nomenclature. It is a bicyclic compound with a pyridine cycle and a pyrrolidine cycle. The molecule possesses an asymetric carbon and so exists in two enantiomeric compounds. In nature, nicotine only exists in the S shape, which is levogyre.
Representation of the S molecule in 2D :
Representationb of the R molecule in 3D :
2 - Properties of Nicotine
| Formula | C10H14N2 |
| Molecular Weight | 162,234 g.mol-1 |
| Melting point | -7,9 ° C |
| Boiling point | 247 ° C |
| Rotatory index (S) |
aD = -168 at 20° C
|
| Density | d=1,010 |
| Refractive index | n=1,530 |
| Comments | Pale yellow to dark brown liquid with a slight, fishy odor when warm. Insecticide. |
3 - IR analysis
On this spectrum, we can notice several peaks, which characterise the different chemical functions of nicotine:
· Around 3400 cm-1, we can see the large peak of water (it deals with a liquid film).· Between 2970 and 2780 cm-1 : C-H stretching.
· The peak at 1677 cm-1 : aromatic C=N double bond stretching.
· The peak at 1691 cm-1 : aromatic C=C double bond stretching.
· The peaks at 717 cm-1 and 904 cm-1 correspond to the out of plane bending of the C-H bond of the monosubstituted pyridinic cycle.
4 - Mass spectrum analysis
We can notice the molecular peak at 162 m/z. However, the biggest peak is at 84 m/z. It corresponds to the fragmentation of nicotine. It deals with the pyrrolidine cycle, which has this molecular weight. During the electronic bombardment, the nicotine was split between the two cycles.
5 - 1H-RMN analysis in CDCl3 (400MHz)
Assignment
|
Chemical shift (ppm)
|
A
|
8,543
|
B
|
8,487
|
C
|
7,711
|
D
|
7,255
|
E
|
3,237
|
F
|
3,087
|
G
|
2,307
|
J
|
2,200
|
K
|
2,160
|
L
|
1,958
|
M
|
1,820
|
N
|
1,725
|
Done with C-H COSY
| |
6 - 13C-RMN analysis in CDCl3
| Assignment | Chemical shift (ppm) | Integration |
| 1 | 149,45 | 750 |
| 2 |
148,51
| 783 |
| 3 | 138,80 | 517 |
| 4 | 134,86 | 917 |
| 5 | 123,54 | 894 |
| 6 | 68,83 | 1000 |
| 7 | 56,96 | 844 |
| 8 | 40,32 | 783 |
| 9 | 35,23 | 833 |
| 10 | 22,60 | 839 |
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DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO
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