Nucleophilic attacks of amines

Nucleophilic attack Nucleophiles Molecules or ions having an atom with a free doublet capable of binding to an electrophilic atom or a cation.

Nucleophilic nature of amines

- The nucleophilic nature of the amines is due to the free electron pair of the N atom ::

...because the rather weak electronegativity of the nitrogen does not retain enough this doublet..

- The nucleophilic nature increases from primary amines to secondary amines:

...because the inductive effect I+ of alkyl groups pushs on the free electrons of the nitrogen atom and makes them more available..

- Nucleophilic character decreases secondary amines to tertiary amines:

...because, despite the inductive effect of the alkyl groups, the steric hindrance of the alkyl groups masks the free electrons of the nitrogen atom and makes them less available..

Nucleophilic attack of an amine (I) on a haloalkane (II): f.i.:

The excess amine can exchange a hydrogen ion with the ammonium ion to form an amine (III) of a higher class..

Nucleophilic attack of an amine (II) on an acid chloride (I): f.i.::

The excess amine can exchange a hydrogen ion with the ammonium ion to form a nitrogen-substituted amide (III)...