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

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DOIResolve DOI: http://doi.org/10.1021/ja071716y
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TypeArticle
Journal titleJournal of the American Chemical Society
Volume129
Pages92809281; # of pages: 2
AbstractQuenching 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.
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AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
NPARC number12327313
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Record identifierfec7221d-227a-4768-9250-811521046270
Record created2009-09-10
Record modified2016-05-09
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