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International Journal of Electrochemistry
Volume 2011, Article ID 346043, 12 pages
http://dx.doi.org/10.4061/2011/346043
Research Article

Integrated Study of the Dinitrobenzene Electroreduction Mechanism by Electroanalytical and Computational Methods

1N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 199991, Russia
2P.G. Demidov Yaroslavl State University, Yaroslavl 150000, Russia

Received 19 July 2010; Revised 20 September 2010; Accepted 20 September 2010

Academic Editor: Jay D. Wadhawan

Copyright © 2011 Andrey S. Mendkovich et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Electroreduction of 1,2-, 1,3-, and 1,4-dinitrobenzenes in DMF has been investigated by a set of experimental (cyclic voltammetry, chronoamperometry, and controlled potential electrolysis) and theoretical methods (digital simulation and quantum chemical calculations). The transformation of only one nitro group is observed in the presence of proton donors. The process selectivity is provided by reactions of radical anions' intermediate products. The key reactions here are protonation of radical anions of nitrosonitrobenzenes and N-O bond cleavage in radical anions of N-(nitrophenyl)-hydroxylamines.