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Solvent effects on the rates and mechanisms of reaction of phenols with free radicals

Par Conseil national de recherches du Canada

DOITrouver le DOI : https://doi.org/10.1021/ar0682029
AuteurRechercher : ; Rechercher : 1
Affiliation
  1. Conseil national de recherches du Canada
FormatTexte, Article
Sujetfree radical; phenol derivative; proton; solvent; water; chemistry; electron transport; hydrogen bond; Electron Transport; Free Radicals; Hydrogen Bonding; Phenols; Protons; Solvents; Water
Résumé
The rates of formal abstraction of phenolic hydrogen atoms by free radicals, Y• + ArOH → YH + ArO•, are profoundly influenced by the hydrogen-bond-accepting and anion-solvation abilities of solvents, by the electron affinities and reactivities (Y-H bond dissociation enthalpies) of radicals, and by the phenol's ring substituents. These apparently simple reactions can occur by at least three different, nonexclusive mechanisms: hydrogen atom transfer, proton-coupled electron transfer, and sequential proton-loss electron transfer. The delicate balance among these mechanisms depends on both the environment and the reactants. The main features of these mechanisms are described, together with some interesting kinetic consequences. © 2007 American Chemical Society.
Date de publication
Dans
  • Accounts of Chemical Research 40, nº 3 (2007) : 222–230.
Langueanglais
Publications évaluées par des pairsOui
Numéro NPARC21276796
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Identificateur de l’enregistrementa200234a-26d4-46e6-a9cf-3555c00efb27
Enregistrement créé2015-10-13
Enregistrement modifié2020-05-10
Date de modification :