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

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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.

About the authors

I. E. Mikhailov

Institute of Physical and Organic Chemistry of Southern Federal University

Email: mie@sfedu.ru
ORCID iD: 0000-0003-1820-4012
Rostov-on-Don, Russia

N. I. Belaya

Donetsk State University

ORCID iD: 0000-0003-3359-3239
Donetsk, Russia

A. V. Belyi

Donetsk State University

ORCID iD: 0000-0001-6837-9211
Donetsk, Russia

Yu. M. Artyushkina

Institute of Physical and Organic Chemistry of Southern Federal University

ORCID iD: 0009-0009-1347-4479
Rostov-on-Don, Russia

G. A. Dushenko

Institute of Physical and Organic Chemistry of Southern Federal University

ORCID iD: 0000-0002-5455-8419
Rostov-on-Don, Russia

V. I. Minkin

Institute of Physical and Organic Chemistry of Southern Federal University

ORCID iD: 0000-0001-6096-503X
Rostov-on-Don, Russia

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