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RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

  • ISSN (Print) 0514-7492
  • ISSN (Online) 3034-6304

SYNTHESIS AND ANTIOXIDANT PROPERTIES OF 1,3,4-OXADIAZOLE DERIVATIVES OF BENZOIC AND MONOHYDROXYBENZOIC ACIDS

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PII
S3034630425070208-1
DOI
10.7868/S3034630425070208
Publication type
Article
Status
Published
Authors
I. E. Mikhailov
  • Affiliation: Institute of Physical and Organic Chemistry of Southern Federal University
N. I. Belaya
  • Affiliation: Donetsk State University
A. V. Belyi
  • Affiliation: Donetsk State University
Yu. M. Artyushkina
  • Affiliation: Institute of Physical and Organic Chemistry of Southern Federal University
G. A. Dushenko
  • Affiliation: Institute of Physical and Organic Chemistry of Southern Federal University
V. I. Minkin
  • Affiliation: Institute of Physical and Organic Chemistry of Southern Federal University
Volume/ Edition
Volume 61 / Issue number 7
Pages
994-1007
Abstract
By interaction of benzoic acid hydrazides with orthoesters of carboxylic acids, 2-aryl- and 2-aryl-5-alkyl-1,3,4-oxadiazoles were synthesized, the antiradical action of which was studied in the reaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH•). In the reaction with DPPH•, phenoloxadiazoles showed higher antiradical activity compared to the corresponding monohydroxybenzoic acids due to intramolecular synergism, which is realized as a result of the combined action of the phenol and oxadiazole fragments within one molecule, leading to resonance stabilization of the resulting phenoxyl radical. For 1,3,4-oxadiazoles, which do not contain a phenolic fragment in their composition and exhibit lower antiradical activity compared to phenoloxadiazoles, a mechanism of their antioxidant action has been proposed, which is associated with the formation of a radical adduct.
Keywords
1,3,4-оксадиазолы моногидроксибензойные кислоты 2,2-дифенил-1-пикрилгидразил антиоксиданты синергизм
Date of publication
01.07.2025
Year of publication
2025
Number of purchasers
0
Views
27

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