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Kinetic solvent effects on the reaction of an aromatic ketone p,p* triplet with phenol. Rate-retarding and rate-accelerating effects of hydrogen-bond acceptor solvents

DOIResolve DOI: https://doi.org/10.1021/ja071716y
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Affiliation
  1. National Research Council Canada. NRC Steacie Institute for Molecular Sciences
FormatText, Article
Abstract
Quenching of the 2-benzoylthiophene π,π* triplet, 3BT*, by phenol yields the corresponding ketyl and phenoxyl radicals. Reaction rates were measured in 10 solvents having a range of hydrogen-bond acceptor strengths (β2H values). There appear to be two mechanisms:  (i) a bimolecular reaction of 3BT* with “free” (i.e., not H-bonded) phenol in which the 3BT* accepts both a proton and an electron from the phenol, the rate decreasing as β2H increases; (ii) a trimolecular reaction of 3BT* with phenol that is H-bonded to a solvent molecule, PhO−H···S, in which the proton goes to the S and the electron to the 3BT*, the rate increasing as β2H increases.
Publication date
In
  • Journal of the American Chemical Society 129 (2007): 9280–9281.
LanguageEnglish
Peer reviewedYes
NPARC number12327313
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Record identifierfec7221d-227a-4768-9250-811521046270
Record created2009-09-10
Record modified2023-04-17

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