Oxidant activity of tris(2,4,6-trichloro-3,5-dinitrophenyl)methyl radical with catechol and pyrogallol. Mechanistic considerations

J Org Chem. 2009 Mar 20;74(6):2368-73. doi: 10.1021/jo802559x.

Abstract

The reducing activity of simple polyphenols (PhOH), catechol and pyrogallol, is tested in different solvents in front of tris(2,4,6-trichloro-3,5-dinitrophenyl)methyl (HNTTM) radical, a stable organic free radical of the TTM series. HNTTM radical is very active in electron-transfer reactions to give a very stable anion. The standard potential for the reduction of HNTTM radical by cyclic voltammetry in different solvents is E(o) = 0.60 +/- 5 V vs SCE. In hydroxylic solvents, the electron transfer is a very rapid process and the electron-donating species is the ionized PhO(-), whereas in nonpolar solvents, it is suggested that the electron transfer is facilitated by the formation of an intermediate complex between HNTTM and PhOH.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catechols / chemistry*
  • Electron Transport
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Organic Chemistry Phenomena
  • Oxidants / chemistry*
  • Pyrogallol / chemistry*
  • Solvents

Substances

  • Catechols
  • Oxidants
  • Solvents
  • Pyrogallol
  • methyl radical
  • Methane