Understanding C-H bond oxidations: H. and H- transfer in the oxidation of toluene by permanganate.
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.
Gardner
K A
KA
Department of Chemistry, University of Washington, Seattle 98195-1700, USA.
Mayer
J M
JM
D002244:Carbon / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D007700:Kinetics; D010084:Oxidation-Reduction; D011196:Potassium Permanganate / Q000737:chemistry*; D012997:Solvents; D013056:Spectrophotometry, Ultraviolet; D013816:Thermodynamics; D014050:Toluene / Q000737:chemistry*
D012997:Solvents; D011196:Potassium Permanganate; D014050:Toluene; D002244:Carbon; D006859:Hydrogen