Mechanistic study of the oxidation of catechol in the presence of secondary amines by digital simulation of cyclic voltammograms

Electrochemical oxidation of catechol (1) has been studied in the presence of morpholine (2a), dimethylamine (2b) and diethylamine (2c) as nucleophile in aqueous solution, using cyclic voltammetry and controlled-potential coulometry. The results indicate that the participation of catechol (1) in Michael reaction with 2 to form the corresponding aminoquinone derivatives (5a-5c). Based on ECE mechanism, the homogeneous rate constants were estimated by comparing the experimental cyclic voltammetric responses with the digital simulated results. (C) 2003 Elsevier Ltd. All rights reserved.