carbamamido

Carbamamido is a term used in organic chemistry to describe a substituent or functional motif that contains a carbamamide linkage, typically represented as -NH-CO-NH2. In this arrangement, a carbonyl carbon is bonded to two nitrogens: one amide nitrogen that connects to the rest of the molecule, and a terminal NH2 group. The resulting group is polar and capable of hydrogen bonding, which can influence solubility and conformation of compounds bearing it.

Structure and connectivity: The characteristic fragment is R-NH-CO-NH2, where R denotes the remainder of the molecule. This creates a two-nitrogen, one-carbonyl motif that resembles a urea-like linkage, distinguishing it from simpler amide or carbamoyl groups.

Occurrence and applications: Carbamamido groups appear mainly in synthetic organic chemistry, particularly in the construction of urea-like linkages and in peptidomimetics. They are less common as motifs in natural products but can arise in intermediates or protected structures during synthesis.

Synthesis and naming: The carbamamido group can be introduced by carbamoylation of an amine using carbamoylating reagents (for example, carbamoyl chlorides) or through condensation with urea derivatives to form the N-CO-N linkage. In naming, a molecule containing the -NH-CO-NH2 fragment may be described with the carbamamido- substituent in IUPAC-style nomenclature.

Safety and handling: Compounds containing carbamamido motifs are treated as amide derivatives. Reagents used to form these linkages, such as carbamoyl chlorides, can be reactive and require standard laboratory precautions.

See also: Carbamoyl group, Urea, Amide, Peptidomimetics.