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Electroreduction mechanism of N-phenylhydroxylamines in aprotic solvents: formation of hydrogen bonds between N-(3-nitrophenyl)hydroxylamine and its radical anion

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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.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. S. Mendkovich, M. A. Syroeshkin & V. P. Gultyai

  2. P. G. Demidov Yaroslavl State University, 14 ul. Sovetskaya, 150000, Yaroslavl, Russian Federation

    A. I. Rusakov

Authors
  1. A. S. Mendkovich
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  2. M. A. Syroeshkin
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  3. V. P. Gultyai
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  4. A. I. Rusakov
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Correspondence to A. S. Mendkovich.

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Mendkovich, A.S., Syroeshkin, M.A., Gultyai, V.P. et al. Electroreduction mechanism of N-phenylhydroxylamines in aprotic solvents: formation of hydrogen bonds between N-(3-nitrophenyl)hydroxylamine and its radical anion. Russ Chem Bull 66, 479–482 (2017). https://doi.org/10.1007/s11172-017-1758-z

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  • DOI: https://doi.org/10.1007/s11172-017-1758-z

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