Current location: JICS Archive > Vol. 7 > No. 1 > Articles : 31

Kinetics Study of Electrochemically Induced Michael Reaction of Benzoquinones with Triphenylphosphine

D. Nematollahi* and R. Esmaili

Faculty of Chemistry, Bu-Ali-Sina University, Hamedan, 65174, Iran

The electrochemical oxidation of 3,4-dihydroxybenzaldehyde (1), 3,4-dihydroxybenzoic acid (2) and 2,5-dihydroxybenzoic acid (3) were studied in the presence of triphenylphosphine (4) as a nucleophile using cyclic voltammetry and controlled-potential coulometry. The results indicate that the quinones derived from oxidation of 3,4-dihydroxybenzaldehyde, 3,4-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid participate in Michael addition reaction with triphenylphosphine (4). In this work, based on an EC mechanism, the observed homogeneous rate constants (k_obs) of the reaction of produced benzoquinones with triphenylphosphine (4) were estimated by comparing the experimental cyclic voltammograms with the digitally simulated results.

Keywords: Digital simulation, Triphenylphosphine, 3,4-Dihydroxybenzaldehyde, EC mechanism, Homogeneous rate constant