Understanding C-H bond oxidations: H. and H- transfer in the oxidation of toluene by permanganate

Science. 1995 Sep 29;269(5232):1849-51. doi: 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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Carbon / chemistry*
  • Hydrogen / chemistry*
  • Kinetics
  • Oxidation-Reduction
  • Potassium Permanganate / chemistry*
  • Solvents
  • Spectrophotometry, Ultraviolet
  • Thermodynamics
  • Toluene / chemistry*

Substances

  • Solvents
  • Potassium Permanganate
  • Toluene
  • Carbon
  • Hydrogen