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

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...

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Main Authors: Andrey S. Mendkovich, Mikhail A. Syroeshkin, Ludmila V. Mikhalchenko, Mikhail N. Mikhailov, Alexander I. Rusakov, Vadim P. Gul'tyai
Format: Article
Language:English
Published: Wiley 2011-01-01
Series:International Journal of Electrochemistry
Online Access:http://dx.doi.org/10.4061/2011/346043
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author Andrey S. Mendkovich
Mikhail A. Syroeshkin
Ludmila V. Mikhalchenko
Mikhail N. Mikhailov
Alexander I. Rusakov
Vadim P. Gul'tyai
author_facet Andrey S. Mendkovich
Mikhail A. Syroeshkin
Ludmila V. Mikhalchenko
Mikhail N. Mikhailov
Alexander I. Rusakov
Vadim P. Gul'tyai
author_sort Andrey S. Mendkovich
collection DOAJ
description 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.
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institution Kabale University
issn 2090-3537
language English
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publisher Wiley
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series International Journal of Electrochemistry
spelling doaj-art-4beac61ef8844d95906fd12aff36985b2025-02-03T01:00:02ZengWileyInternational Journal of Electrochemistry2090-35372011-01-01201110.4061/2011/346043346043Integrated Study of the Dinitrobenzene Electroreduction Mechanism by Electroanalytical and Computational MethodsAndrey S. Mendkovich0Mikhail A. Syroeshkin1Ludmila V. Mikhalchenko2Mikhail N. Mikhailov3Alexander I. Rusakov4Vadim P. Gul'tyai5N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 199991, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 199991, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 199991, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 199991, RussiaP.G. Demidov Yaroslavl State University, Yaroslavl 150000, RussiaN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 199991, RussiaElectroreduction 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.http://dx.doi.org/10.4061/2011/346043
spellingShingle Andrey S. Mendkovich
Mikhail A. Syroeshkin
Ludmila V. Mikhalchenko
Mikhail N. Mikhailov
Alexander I. Rusakov
Vadim P. Gul'tyai
Integrated Study of the Dinitrobenzene Electroreduction Mechanism by Electroanalytical and Computational Methods
International Journal of Electrochemistry
title Integrated Study of the Dinitrobenzene Electroreduction Mechanism by Electroanalytical and Computational Methods
title_full Integrated Study of the Dinitrobenzene Electroreduction Mechanism by Electroanalytical and Computational Methods
title_fullStr Integrated Study of the Dinitrobenzene Electroreduction Mechanism by Electroanalytical and Computational Methods
title_full_unstemmed Integrated Study of the Dinitrobenzene Electroreduction Mechanism by Electroanalytical and Computational Methods
title_short Integrated Study of the Dinitrobenzene Electroreduction Mechanism by Electroanalytical and Computational Methods
title_sort integrated study of the dinitrobenzene electroreduction mechanism by electroanalytical and computational methods
url http://dx.doi.org/10.4061/2011/346043
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