R1CONR2R3

R1CONR2R3 is a general structural formula used in organic chemistry to denote a class of carboxamide compounds in which a carbonyl group (C=O) is bound to an R1 group on the carbon and to a nitrogen atom bearing two substituents, R2 and R3. In this representation, the carbonyl carbon is part of the acyl fragment R1CO, and the amide nitrogen carries the two substituents R2 and R3, which can be alkyl, aryl, or other substituents.

Amide compounds described by R1CONR2R3 exhibit characteristic resonance that stabilizes the C–N bond, giving the amide a planar geometry and partial double-bond character. This resonance reduces the reactivity of the carbonyl toward nucleophiles and contributes to the relatively high stability and low basicity of the amide nitrogen compared with other amines. Physical properties such as polarity and hydrogen-bonding capacity depend on the nature of R1, R2, and R3.

Common examples include N,N-disubstituted amides such as N,N-dimethylacetamide (CH3-CO-N(CH3)2), where R1 is a methyl group and R2/R3 are both methyl groups. Other examples include N,N-diethylbenzamide and related aryl- or alkyl-substituted amides.

Synthesis typically involves coupling a carboxylic derivative (such as an acid chloride or an anhydride) with a secondary amine, or direct amidation of carboxylic acids under dehydrating conditions. Reactions of amides include hydrolysis to yield the corresponding carboxylic acid and amine, and selective reduction under suitable conditions.

See also: Amide, N-substituted amide, carboxamide.