Oxidation and complexation of benzamide with transition metal ions

CHED 1225

John D. Kromer, jkromer@transy.edu, Chemistry Program, Transylvania University, 300 N Broadway, Lexington, KY 40508 and Gerald L. Seebach, Division of Natural Science and Mathematics, Transylvania University, 300 N. Broadway, Lexington, KY 40508.
The complexation of copper (II) chloride with amides has been studied for several years. The reaction of copper (II) chloride, benzamide, and persulfate has resulted in the formation of N,N'-diphenylurea, originally thought to form through a reaction between water and phenylisocyanate, created by the oxidation of benzamide by persulfate. A reaction of copper (II) chloride and phenylisocyanate resulted in purple crystals; spectral analysis indicated that the identity of the crystals was pure N,N'-diphenylurea, despite the purple color. This research characterizes the crystals to understand how they could be produced in the absence of water. The reaction happened too quickly for the mechanism to be studied, so this research replaces the copper with chromium or vanadium, in order to slow down the reaction and investigate a variety of possible oxidation states of the metal ion.