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2009•Russian Journal of Physical Chemistry ARequires access

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

Isidora Cekić-Lasković, Dragica M. Minić, Marija Baranac‐Stojanović, Radmila Marković, Elena Volanschi

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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: =CHCO 2 Et; EWG: CONHPh), consisting as a (2 E ,5 Z )/(2 Z ,5 Z ) mixture, by cyclic voltammetry in polar as well as non-polar solvent (0.1 M TBAHFP in DMSO and CHCl 3 , 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.

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What this paper is about

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: =CHCO 2 Et; EWG: CONHPh), consisting as a (2 E ,5 Z )/(2 Z ,5 Z ) mixture, by cyclic voltammetry in polar as well as non-polar solvent (0.1 M TBAHFP in DMSO and CHCl 3 , 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.

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Available 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: =CHCO 2 Et; EWG: CONHPh), consisting as a (2 E ,5 Z )/(2 Z ,5 Z ) mixture, by cyclic voltammetry in polar as well as non-polar solvent (0.1 M TBAHFP in DMSO and CHCl 3 , 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.

Key concepts: Cyclic voltammetry, Electrochemistry, Substituent, Chemistry, Isomerization, Solvent, Electron transfer, Polar

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