The effect of the medium polarity on the mechanism of the reaction of hydroxybenzenes with hydrazyl radical in aprotic solvents
- Authors: Belaya N.I.1, Belyj A.V.1, Zarechnaya O.M.2, Scherbakov I.N.3, Mikhalchuk V.M.1, Doroshkevich V.S.1
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Affiliations:
- Donetsk National University
- Litvinenko Institute of Physico-Organic Chemistry and Coal Chemistry
- Southern Federal University
- Issue: Vol 87, No 4 (2017)
- Pages: 690-697
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/219156
- DOI: https://doi.org/10.1134/S1070363217040053
- ID: 219156
Cite item
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.
About the authors
N. I. Belaya
Donetsk National University
Author for correspondence.
Email: nat.iv.belaya@gmail.com
Ukraine, ul. Universitetskaya 24, Donetsk, 83001
A. V. Belyj
Donetsk National University
Email: nat.iv.belaya@gmail.com
Ukraine, ul. Universitetskaya 24, Donetsk, 83001
O. M. Zarechnaya
Litvinenko Institute of Physico-Organic Chemistry and Coal Chemistry
Email: nat.iv.belaya@gmail.com
Ukraine, Donetsk
I. N. Scherbakov
Southern Federal University
Email: nat.iv.belaya@gmail.com
Russian Federation, Rostov-on-Don
V. M. Mikhalchuk
Donetsk National University
Email: nat.iv.belaya@gmail.com
Ukraine, ul. Universitetskaya 24, Donetsk, 83001
V. S. Doroshkevich
Donetsk National University
Email: nat.iv.belaya@gmail.com
Ukraine, ul. Universitetskaya 24, Donetsk, 83001