4.6 Article

Electrochemical behavior of 2-aminodiphenylamine and efficient factors on the site-selectivity of sulfonylation reaction: Experimental and theoretical studies

Journal

ELECTROCHIMICA ACTA
Volume 222, Issue -, Pages 845-855

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.electacta.2016.11.046

Keywords

2-Aminodiphenylamine; Regioselective sulfonation; Natural charge; NBO analysis; Cyclic voltammetry; Antibacterial activity; EDA analysis

Funding

  1. Bu-Ali Sina University
  2. University of Kurdistan

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The electrochemical dimerization of 2-aminodiphenylamine (2ADPA) has been studied. The data indicate that electrochemically generated (Z)-N-(6-iminocyclohexa-2,4-dien-1-ylidene) aniline (2ADPA.) can serve as a Michael acceptor in the reaction with starting molecular (2ADPA) form and converts to the corresponding dimer. The mechanism of dimerization has been studied using both controlled-potential coulometry and cyclic voltammetry. The anodic dimerization of 2-aminodiphenylamine has been successfully performed under constant current condition in good yield and purity in an undivided cell. Furthermore, electrochemical oxidation of 2ADPA has been studied both experimentally and theoretically to provide insight into the influence of some factors on the type of chemical reaction which follows 2ADPA(OX). The effect of natural charge of 2ADPA(OX) on the reaction site was calculated using PBE/def2-SVP level of theory to identify regioselective sulfonation of 2ADPA. The results indicate that the natural charge of Michael acceptor 2ADPA(OX) and thermodynamic stability of products lead to site-selectivity sulfonylation of 2ADPA. In addition, the sulfone products were evaluated for their in vitro antibacterial activity against two bacterial ATCC strains (Staphylococcus aureus, and Escherichia coli). (C) 2016 Elsevier Ltd. All rights reserved.

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