Russian Journal of General Chemistry

, Volume 87, Issue 4, pp 690–697

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

  • N. I. Belaya
  • A. V. Belyj
  • O. M. Zarechnaya
  • I. N. Scherbakov
  • V. M. Mikhalchuk
  • V. S. Doroshkevich
Article
  • 14 Downloads

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.

Keywords

hydroxybenzene 2,2′-diphenyl-1-picrylhydrazyl antiradical activity reaction mechanism 

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Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  • N. I. Belaya
    • 1
  • A. V. Belyj
    • 1
  • O. M. Zarechnaya
    • 2
  • I. N. Scherbakov
    • 3
  • V. M. Mikhalchuk
    • 1
  • V. S. Doroshkevich
    • 1
  1. 1.Donetsk National UniversityDonetskUkraine
  2. 2.Litvinenko Institute of Physico-Organic Chemistry and Coal ChemistryDonetskUkraine
  3. 3.Southern Federal UniversityRostov-on-DonRussia

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