Electroreduction mechanism of N-phenylhydroxylamines in aprotic solvents: formation of hydrogen bonds between N-(3-nitrophenyl)hydroxylamine and its radical anion
- Authors: Mendkovich A.S.1, Syroeshkin M.A.1, Gultyai V.P.1, Rusakov A.I.2
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Affiliations:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- P. G. Demidov Yaroslavl State University
- Issue: Vol 66, No 3 (2017)
- Pages: 479-482
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/240178
- DOI: https://doi.org/10.1007/s11172-017-1758-z
- ID: 240178
Cite item
Abstract
The electroreduction of N-(3-nitrophenyl)hydroxylamine in DMF was studied using cyclic voltammetry, chronoamperometry, and numerical simulation. It is shown that the stability of formed radical anion is significantly higher than that of the radical anion of the 4-nitrophenyl derivative. In the range of low concentrations and high potential scan rates, the electroreduction of N-(3-nitrophenyl)hydroxylamine is complicated only by the formation of complexes between the depolarizer molecules, most likely, due to hydrogen bonds, as well as between the depolarizer and its radical anion. The thermodynamic and kinetic parameters of these processes were evaluated.
About the authors
A. S. Mendkovich
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Author for correspondence.
Email: asm@free.net
Russian Federation, 47 Leninsky prosp., Moscow, 119991
M. A. Syroeshkin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: asm@free.net
Russian Federation, 47 Leninsky prosp., Moscow, 119991
V. P. Gultyai
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: asm@free.net
Russian Federation, 47 Leninsky prosp., Moscow, 119991
A. I. Rusakov
P. G. Demidov Yaroslavl State University
Email: asm@free.net
Russian Federation, 14 ul. Sovetskaya, Yaroslavl, 150000