Understanding C-H Bond Oxidations: H⋅ and H - Transfer in the Oxidation of Toluene by Permanganate
- 29 September 1995
- journal article
- other
- Published by American Association for the Advancement of Science (AAAS) in Science
- Vol. 269 (5232) , 1849-1851
- https://doi.org/10.1126/science.7569922
Abstract
The oxidation of toluene by permanganate has been studied as a model for the oxidation of C-H bonds by metal reagents, metalloenzymes, and metal oxide surfaces. In water, the reaction proceeds by hydride (H-) transfer from toluene to a permanganate oxygen, whereas in toluene solution, permanganate abstracts a hydrogen atom (H.). The ability of permanganate to abstract a hydrogen atom is rationalized on the basis of the strong O-H bond formed on H. addition to permanganate. This approach allows understanding and prediction of the rates of hydrogen atom transfer from substrates to metal active sites.Keywords
This publication has 25 references indexed in Scilit:
- Three methods to measure RH bond energiesThe Journal of Physical Chemistry, 1994
- C-H Bond Activation by Metal Oxo Species: Oxidation of Cyclohexane by Chromyl ChlorideJournal of the American Chemical Society, 1994
- The Uncatalyzed Transfer Hydrogenation of α‐Methylstyrene by Dihydroanthracene or Xanthene—a Radical ReactionAngewandte Chemie International Edition in English, 1992
- Mechanistic and kinetic studies of the reactions of gas-phase methyl radicals with metal oxidesJournal of the American Chemical Society, 1991
- DOPAMINE BETA-HYDROXYLASE OF ADRENAL CHROMAFFIN GRANULES: STRUCTURE AND FUNCTIONAnnual Review of Biochemistry, 1988
- Critical Review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (⋅OH/⋅O− in Aqueous SolutionJournal of Physical and Chemical Reference Data, 1988
- Oxidation of hydrocarbons. 14.Autocatalysis during the oxidation of 1-tetradecene by methyltributylammonium permanganateCanadian Journal of Chemistry, 1985
- Kinetics and mechanism of oxidation of aromatic hydrocarbons by Ru(trpy)(bpy)O2+Journal of the American Chemical Society, 1982
- Oxidation of Hydrocarbons with Benzyl(triethyl)ammonium PermanganateAngewandte Chemie International Edition in English, 1979
- Kinetic studies of the oxidation of aromatic compounds by potassium permanganate. Part I. TolueneJournal of the Chemical Society, 1955