Phenol ring nitration induced by the unprecedented reduction of the Cu(II) centre by nitrogen dioxide

Dalton Trans. 2013 Dec 14;42(46):16264-7. doi: 10.1039/c3dt51642c.

Abstract

Nitrogen dioxide (˙NO2) induces tyrosine nitration through a radical mechanism in biological systems. Two copper(II) complexes, 1 and 2, with ligands L₁ and L₂ [L₁ = 2,4-di-tert-butyl-6-(((2-(dimethylamino)ethyl)(isopropyl)amino)methyl)phenol; L₂ = 6,6'-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(2,4-di-tert-butylphenol)], respectively, have been made to react with ˙NO2. In both cases, the reduction of the copper(II) center was observed in the presence of ˙NO2 which induces phenol ring nitration through nitronium ion (NO2(+)) formation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coordination Complexes / chemistry
  • Copper / chemistry*
  • Crystallography, X-Ray
  • Ions / chemistry
  • Molecular Conformation
  • Nitro Compounds / chemistry
  • Nitrogen Dioxide / chemistry*
  • Oxidation-Reduction
  • Phenol / chemistry*
  • Reactive Nitrogen Species / chemistry

Substances

  • Coordination Complexes
  • Ions
  • Nitro Compounds
  • Reactive Nitrogen Species
  • Phenol
  • Copper
  • Nitrogen Dioxide