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

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1021/ar0682029
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  1. National Research Council Canada
FormatText
TypeArticle
Journal titleAccounts of Chemical Research
ISSN0001-4842
Volume40
Issue3
Pages222–230; # of pages: 9
Subjectfree radical; phenol derivative; proton; solvent; water; article; chemistry; electron transport; hydrogen bond; Electron Transport; Free Radicals; Hydrogen Bonding; Phenols; Protons; Solvents; Water
Abstract
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.
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LanguageEnglish
Peer reviewedYes
NPARC number21276796
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