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Schiff base[′shif ‚bās]
any one of a class of organic compounds with the general formula RR′C═NR″, where R and R′ represent hydrogen, an alkyl, or an aryl and R″ is an alkyl or aryl; in the latter case, Schiff bases are also called anils.
Schiff bases are crystalline or oily substances that are insoluble in water and soluble in organic solvents. They are weak bases, forming salts with acids in an anhydrous medium; in aqueous acid solutions they undergo hydrolysis to yield an amine and aldehyde. The majority of Schiff bases are stable in alkaline solutions. Schiff bases undergo hydrogenation to give secondary amines (RR′CH—NHR″) and add on many compounds containing mobile hydrogen, such as (β-dicarbonyl compounds, ketones, and imines. They are produced mainly by the condensation of aldehydes or ketones with primary amines.
The reaction was first completed by H. Schiff in 1864 (hence the name of the compounds). Schiff bases are valuable intermediate products of organic synthesis, for example, in the preparation of secondary amines and various heterocyclic compounds. The Schiff bases known as azomethine dyes are used for dyeing acetate and synthetic fibers; they are also used in color photography to reduce the photosensitivity of photographic emulsions.