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JOURNALS // Uspekhi Khimii // Archive

Usp. Khim., 2009 Volume 78, Issue 11, Pages 1129–1155 (Mi rcr195)

This article is cited in 36 papers

The reactivity of natural phenols

E. T. Denisov, T. G. Denisova

Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow region

Abstract: This review surveys physicochemical data of natural phenols published in recent years. The structures of some compounds of this class are given. A complete set of the dissociation energies of the O–H bonds for 71 natural phenols is presented. Kinetic characteristics of the reactions of peroxyl, alkyl and thiyl radicals with natural phenols, exchange reactions of phenoxyl radicals with phenols and reactions of phenoxyl radicals with lipids, hydroperoxides, cysteine and ascorbic acid are compiled and described systematically. The reactivity of phenols in radical reactions and the factors that determine the reactivity (the enthalpy of reaction, triplet repulsion, the electronegativities of atoms at the reaction centre, the presence of π-electrons adjacent to the reaction centre, the radii of atoms at the reaction centre, steric hindrance, the force constants of the reacting bonds) are discussed. An important role of hydrogen bonding between surrounding molecules and the OH groups of natural phenols in decreasing their reactivities is noted.

Received: 02.06.2009

DOI: 10.1070/RC2009v078n11ABEH004084


 English version:
Russian Chemical Reviews, 2009, 78:11, 1047–1073

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