Chapter 21: Amines. Organic derivatives of ammonia, NH
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223 Chapter 21: Amines. Organic derivatives of ammonia, NH 3 . Nitrogen atoms have a lone pair of electrons, making the amine both basic and nucleophilic 21.1: Amines Nomenclature. (please read) Amines are classified according to the degree of nitrogen substitution: 1° (RNH 2 ), 2° (R 2 NH), 3° (R 3 N) and 4° (R 4 N + ) N C H sp 3 N H H H alkylamines arylamines primary (1°) amines secondary (2°) amines tertiary (3°) amines quarternary (4°) ammonium ion NH 2 N H N H 3 CH 2 C N CH 2 CH 3 CH 2 CH 3 H H N H H 3 C N Note: Although the terminology is the same, the classification of amines is different from that of alcohols. 224 21.2: Structure and bonding. The nitrogen of alkylamines is sp 3 hybridized and tetrahedral. The nitrogen of arylamines (aniline) is slightly flatten, reflecting resonance interactions with the aromatic ring.
Transcript of Chapter 21: Amines. Organic derivatives of ammonia, NH
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C9H13NO [α]D +23°
13C NMR: 138.6, 129.1, 128.5, 126.3, 65.9, 54.2, 40.6
7.21-7.32 (m, 2H) 7.15-7.21 (m, 3H)
3.60 (1H, dd, J= 10.7, 4.1)
3.38 (1H, dd, J= 10.7, 7.0)
3.05-3.12 (1H, m)
2.77 (1H, dd, J= 13.3, 5.0)
2.49 (1H, dd, J= 13.3, 8.8)
2.35-2.45 (3H, br s)
IR:
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Alkaloids: Naturally occurring compounds that contain a basic nitrogen atom
N
NCH3
nicotine
NH3C
CO2CH3
O Ph
Ococaine
O
HO
NCH3
HH
HO
morphine
NH
N
HO
H3CO
H
quinine
NH2
OCH3
H3CO
H3CO
mescaline
NH
coniine
N
NH
HO2C
H
CH3
lysergic acid
N
CH3
NCH3 CH3
OO
NHH3C
physostigmine
NH
OH
Histrionicotoxin
N
O
N
OH
H
H
H
strychnine
NH
NHO
MeO2C
NMeO
N
HOH
CO2CH3
O
O
RR= -CH3 vinblastineR= -CHO vincristine
CO2H
HONH2 N
H
NH2
tyrosine tryptophan
CO2H NH2
HO
HO
dopamine
HO
NH
NH2
serotonin
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