Synthesis and properties of some 1,1'-bis[N-formyl-N'-substituted thiourea]ferrocene derivatives: Crystal structure of 1,1'-bis[N-formyl-N'-p-chlorophenylthiourea]ferrocene

A series of 1,1'-bis[N-formyl-N'-substituted thiourea]ferrocene derivatives was synthesized through the reaction of 1,1'-bis[formyl isothiocyanate]ferrocene and various primary amines, with high yields after simple and convenient purification. All the compounds were characterized by elemental analysis, IR and H-1 NMR spectra. Intramolecular hydrogen bonding between the formyl carbonyl group and the proton attached to N' was found to be common in this kind of compound. Cyclic voltammetric analysis revealed that the substituents on the N' atom affect the electrochemical behaviour of the ferrocenyl group via the intramolecular hydrogen bonded ring. The crystal structure of 1,1'-[N-formyl-N'-p-chlorophenylthiourea]ferrocene was determined showing the character of the intramolecular hydrogen bonding. (C) 1997 Elsevier Science Ltd.