Reactions of arylamine and aminophenol derivatives, and riboflavin with organic radicals

Free Radic Res. 2004 Nov;38(11):1183-90. doi: 10.1080/10715760400016162.

Abstract

Based on product yield data on radiolysis of hexane, ethanol and 3 M aqueous ethylene glycol solutions, the ability of a number of arylamine, aminophenol and quinonimine derivatives to affect processes involving peroxyl, alkyl or alpha-hydroxyalkyl radicals was assessed. It has been shown that the introduction of a hydroxyl group into aromatic amine structure enhances its antioxidant performance and makes it significantly more reactive with respect to carbon-centered organic radicals. Replacement of the hydrogen atom of a hydroxyl group by a methyl group decreases the anti-radical activity of aminophenols drastically. Compounds containing (or capable of forming) a quinonimine moiety interact with alkyl or alpha-hydroxyalkyl radicals most effectively, suppressing recombination and fragmentation reactions of the latter. In the sequence: aromatic amines--aminophenols--quinonimines, a trend towards enhancement of the ability of the compounds studied to react with carbon-centered radicals was noted. Also, this study presents for the first time evidence of riboflavin reactivity with respect to organic radicals.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Amines / chemistry*
  • Aminophenols / chemistry*
  • Aminophenols / pharmacology
  • Free Radicals / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Peroxides / chemistry
  • Riboflavin / chemistry*
  • Riboflavin / pharmacology

Substances

  • Amines
  • Aminophenols
  • Free Radicals
  • Peroxides
  • Riboflavin