Cyclic voltammetry study of (5-ethoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)-N-phenylethanamide

Abstract

As a continuation of our ongoing project on electrochemical properties of push-pull 5-substituted 2-alkylidene-4-oxothiazolidines (1a) differing in substituent R at C5-position and electron withdrawing group (EWG), we nave investigated the electrochemical behaviour of (5-etoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)-N-phenylethanamide 1a (R: =CHCO2Et; EWG: CONHPh), consisting as a (2E,5Z)/(2Z,5Z) mixture, by cyclic voltammetry in polar as well as non-polar solvent (0.1 M TBAHFP in DMSO and CHCl3, respectively). Cyclic voltammetry at stationary electrode was employed to characterize the electron transfer steps. Based on electrochemical criteria and correlation with the DigiSim simulations, an ECE mechanism, involving two electrochemical steps and one isomerisation step, was suggested.