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Amines
Amines
Background:
Amines are derivatives of the ammonia NH
3
atom, created when hydrogen atoms attached to the central nitrogen atom are substituted by alkyl groups. The amines are referred to primary, secondary or tertiary amines depending on whether one, two or three hydrogens have been replaced by alkyl groups.
Aromatic amines have the nitrogen atom connected to an
aromatic ring
.
Physical Properties:
Amines have strong, characteristic, disagreeable odors, and are often toxic. The smells of ammonia, fish, urine and rotting flesh are all mainly composed of amines. Biological activities produce amines by breakdown of amino acids.
Methyl-, dimethyl-, trimethyl-, and ethylamine are gases under standard conditions, while diethylamine and triethylamine are liquids. Most other common alkyl amines are liquids; high molecular weight amines are solids.
Most
aliphatic amines
are generally soluble in water, however solubility decreases sharply when the number of carbon atoms exceed 6.
Uses and Applications:
Amines that are isolated from plants are known as alkaloids. Examples of naturally occurring amines include nicotine an ingredient in tobacco smoke, coniine the active ingredient in hemlock, the poison used to execute Socrates and strychnine which is a well known poison. Narcotics containing amines include morphine, quinine, cocaine, heroin and LSD.
Laboratory Preparation:
Amines can be formed by a substitution reactions of alkyl halides with ammonia or with a primary or secondary amine.
The halide ion combines with a hydrogen atom attached to the nitrogen atom and the alkl group from the halogen halide attaches to the nitrogen where the hydrogen was removed.
NH
3
+ C
2
H
5
-Cl --> C
2
H
5
-NH
2
+ HCl
Naming Conventions:
Lower amines are named with the suffix "-amine".
NH
2
-CH
3
--> methylamine
Higher amines have the prefix amino as a functional group.
C
5
H
11
-NH
2
--> 2-aminopentane
Bibliography:
Perdue University article on amines
Wikipedia article on amines
Medical School Practice Exam
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