CHAPTER VI - AROMATIC AMINES

Abstract

The aromatic amines are an industrially important class of organic compounds being widely used in the production of compounds and intermediates for the dyestuff, rubber-processing, and drug-manufacturing industries. Most aromatic amines possess the expected basic character that results from the presence of the lone pair of electrons on the nitrogen atom and like the aliphatic amines, they usually form stable salts with inorganic and also with many organic acids. They are, however, considerably weaker bases than ammonia or the aliphatic amines, and this reduced basicity may be interpreted as resulting from the direct attachment of the nitrogen atom to the aromatic system. Primary aromatic amines undergo N -alkylation on heating with an alkyl halide to give successively secondary amines, tertiary amines, and, finally, quaternary ammonium halides. Primary aromatic amines condense with aromatic aldehydes, but less readily with ketones, to form anils (Schiff bases). Tertiary amines cannot react with aldehydes to form anils.