amide

amide, any member of either of two classes of nitrogen-containing compounds related to ammonia and amines. The covalent amides are neutral or very weakly acidic substances formed by replacement of the hydroxyl group (OH) of an acid by an amino group (NR₂, in which R may represent a hydrogen atom or an organic combining group such as methyl, CH₃). The carboxamides (R′CONR₂), which are derived from carboxylic acids (R′COOH), are the most important group. Sulfonamides (RSO₂NR₂) are similarly related to the sulfonic acids (RSO₃H).

Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.

Covalent amides derived from ammonia are solids, except formamide, which is liquid; those containing fewer than five carbon atoms are soluble in water. They are nonconductors of electricity and solvents for both organic and inorganic substances. Covalent amides, even those of low molecular weight, have high boiling points.

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There are no practical natural sources of simple covalent amides, although polyamides (amides linked together to form large molecules called polymers) occur in great abundance as the protein of living systems. Simple amides ordinarily are prepared by reaction of acids or acid halides with ammonia or amines. They can also be produced by the reaction of water with nitriles.

The characteristic reaction of covalent amides is hydrolysis (a chemical reaction with water), by which they are converted to acids and amines; this reaction ordinarily is slow unless it is catalyzed by a strong acid, an alkali, or an enzyme. Amides also can be dehydrated to nitriles. Amides are not readily oxidized nor reduced, although hydrogenation (addition of hydrogen at high temperatures and pressures) in the presence of a catalyst will convert most amides of carboxylic acids to amines. The powerful reducing agent lithium aluminum hydride transforms amides into amines. Reaction of amides with acid chlorides or anhydrides produces imides, which are compounds with two carbonyl (CO) groups attached to the same nitrogen atom.

Among the amides of commercial importance are acetamide, also called ethanamide (CH₃CONH₂) and dimethylformamide HCON(CH₃)₂, which are used as solvents, the sulfa drugs, and the nylons. Urea or carbamide [CO(NH₂)₂] is a crystalline compound that is formed as the end product of the metabolism of protein and excreted in the urine of mammals. It is synthesized in large quantities from ammonia and carbon dioxide for use in fertilizers, in animal feed, and in manufacturing a class of polymers known as urea-formaldehyde resins, used in making plastics.