Oxidation of nitroxyl radicals: Electrochemical and computational studies

Masatoshi Shibuya, Fabio Pichierri, Masaki Tomizawa, Shota Nagasawa, Iwao Suzuki, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)


We have developed azaadamantane-type nitroxyl radicals (AZADOs) and azabicyclo-type nitroxyl radicals (ABNOs) as highly active alcohol oxidation catalysts. Herein, the electrochemical properties of these nitroxyl radicals were investigated by measuring their formal potentials using cyclic voltammetry (CV). The redox potentials were rationalized with the aid of density functional theory (DFT) calculations. A good correlation between the experimental redox potential and the DFT-computed energy differences (ΔE) between nitroxyl radicals and oxoammonium species was obtained, which shows the effectiveness of DFT in predicting the redox potentials of nitroxyl radicals. Redox potential appears to be an important factor of catalytic activity.

Original languageEnglish
Pages (from-to)2070-2073
Number of pages4
JournalTetrahedron Letters
Issue number16
Publication statusPublished - 2012 Apr 18


  • Cyclic voltammetry
  • DFT calculation
  • Nitroxyl radical
  • Organocatalysis
  • Redox potential

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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