Synthesis, characterization, and crystal structures of,'-bis-(2-di-alkyl-amino-phen-yl)thio-ureas.

Abstract

Two thiourea derivatives, N,N'-bis[2-(dimethylamino)phenyl]thiourea and N,N'-bis[2-(diethylamino)phenyl]thiourea, were obtained by reacting 1,1'-thiocarbonyldiimidazole with two equivalents of the corresponding 2-amino-N,N-dialkylaniline. X-ray crystallographic analysis revealed intramolecular hydrogen bonding between the thiourea N-H groups and the dialkylaminophenyl nitrogen atoms. The remaining N-H bonds participate in intermolecular interactions with sulfur atoms of C=S groups in neighboring molecules within the crystal packing. Spectroscopic characterization by NMR and IR confirmed the structural assignments derived from crystallography.