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

@article{Litwinienko2007SolventEO,
  title={Solvent effects on the rates and mechanisms of reaction of phenols with free radicals.},
  author={Grzegorz Litwinienko and Keith Usherwood Ingold},
  journal={Accounts of chemical research},
  year={2007},
  volume={40 3},
  pages={
          222-30
        }
}
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… CONTINUE READING
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