carbamimidoyl

Carbamimidoyl is a functional group in organic chemistry with the general formula R-C(=NR')NR''R''', where R is an organic substituent. It is essentially a derivative of urea where one of the oxygen atoms is replaced by a carbon-nitrogen double bond, or a derivative of guanidine with one of the amino groups replaced by a hydroxyl group. More precisely, it can be considered as an amidine where one of the nitrogen atoms is further substituted. The carbamimidoyl group is also known as an imidocarbamoyl group.

The carbamimidoyl group is found in various biologically active molecules. For instance, it is a key component of the arginine side chain, which is an amino acid. In this context, it is referred to as a guanidino group. The guanidino group is highly basic due to the delocalization of the positive charge over the three nitrogen atoms.

Carbamimidoyl groups can participate in various chemical reactions. They can be hydrolyzed to form urea derivatives and amines. They can also react with electrophiles at the nitrogen atoms. The synthesis of carbamimidoyl compounds often involves reactions of isocyanates or isothiocyanates with amines, or the reaction of amidines with reagents that introduce a carbonyl-like moiety. Understanding the chemistry of the carbamimidoyl group is important for the synthesis and study of many organic compounds, including pharmaceuticals and natural products.