Preparation and characterization of persistent maltose-conjugated triphenylmethyl radicals

J Org Chem. 2012 Jan 20;77(2):1081-6. doi: 10.1021/jo202356u. Epub 2012 Jan 4.

Abstract

The condensation reaction of D-maltose to free radicals of the series of tris(2,4,6-trichlorophenyl)methyl (TTM) and tris(perchlorophenyl)methyl (PTM) has been described for the first time. The new persistent radicals 1 and 2 are very stable and have been characterized by EPR. Their cyclic voltammograms show a quasi-reversible process in the cathode, being reduced to the corresponding anions, with redox potentials a little lower than those of TTM and PTM, respectively. Their oxidant activity is in close relation with their reduction potentials. Therefore, while 2 is reduced by ascorbic acid, 1 remains unaltered.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemistry
  • Ascorbic Acid / chemistry
  • Chemistry Techniques, Synthetic
  • Electron Spin Resonance Spectroscopy
  • Free Radicals / chemistry
  • Maltose / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Solubility
  • Terphenyl Compounds / chemical synthesis*
  • Terphenyl Compounds / chemistry

Substances

  • Anions
  • Free Radicals
  • Terphenyl Compounds
  • Maltose
  • Ascorbic Acid