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The effect of the medium polarity on the mechanism of the reaction of hydroxybenzenes with hydrazyl radical in aprotic solvents

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Abstract

Mechanisms of the reaction of di- and trihydroxybenzenes with 2,2′-diphenyl-1-picrylhydrazyl (stable radical) in aprotic media of different polarity have been elucidated by experimental and quantum-chemical methods. Kinetic, stoichiometric, and activation parameters of the reaction have been determined. In benzene (nonpolar solvent), the studied reaction occurs via the hydrogen atom transfer mechanism; in the polar solvent with weak ionizing ability (i.e. DMSO), the reaction predominantly occurs via the faster mechanism of coupled electron and proton transfer.

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Authors and Affiliations

  1. Donetsk National University, ul. Universitetskaya 24, Donetsk, 83001, Ukraine

    N. I. Belaya, A. V. Belyj, V. M. Mikhalchuk & V. S. Doroshkevich

  2. Litvinenko Institute of Physico-Organic Chemistry and Coal Chemistry, Donetsk, Ukraine

    O. M. Zarechnaya

  3. Southern Federal University, Rostov-on-Don, Russia

    I. N. Scherbakov

Authors
  1. N. I. Belaya
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  2. A. V. Belyj
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  3. O. M. Zarechnaya
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  4. I. N. Scherbakov
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  5. V. M. Mikhalchuk
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  6. V. S. Doroshkevich
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Correspondence to N. I. Belaya.

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Original Russian Text © N.I. Belaya, A.V. Belyj, O.M. Zarechnaya, I.N. Scherbakov, V.M. Mikhalchuk, V.S. Doroshkevich, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 4, pp. 556–564.

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Belaya, N.I., Belyj, A.V., Zarechnaya, O.M. et al. The effect of the medium polarity on the mechanism of the reaction of hydroxybenzenes with hydrazyl radical in aprotic solvents. Russ J Gen Chem 87, 690–697 (2017). https://doi.org/10.1134/S1070363217040053

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  • DOI: https://doi.org/10.1134/S1070363217040053

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