Biomimetic Oxidation of Diphenyl Sulfide by Meso-Tetraphenyl-Porphyrinatochromium (3+) Chloride as an Electrochemical P-450 Model Compound

Mitsuko Maeda and Takashi Mich

Abstract

Controlled potential electrolysis (CPE) of meso-tetraphenylporphyrinatochromium (3+) chloride (CrTPP, 1 mM) at -1.23 V (vs. Ag-AgCl) in acetonitrile containing diphenyl sulfide (1 mM) and sodium perchlorate (0.1 mM) as the, supporting electrolyte with a glassy carbon cathode gave diphenyl sulfoxide. The addition of acetic acid to the electrolyte solution increased the yield of diphenyl sulfoxide, as did the addition of KO2 to acetonitrile containing diphenyl sulfide. The catalytic cycle is thus similar to that of cytochrome P-450, an important drug-metabolizing enzyme.