Synthesis, structure and reactivity of [o-(2,6-diisopropylphenyliminomethinyl)phenyl]selenenyl selenocyanate (RSeSeCN) and related derivatives

Dalton Trans. 2014 Jul 7;43(25):9431-7. doi: 10.1039/c4dt00157e.

Abstract

The synthesis and the first X-ray structural characterization of a selenenyl selenocyanate, [o-(2,6-diisopropylphenyliminomethinyl)phenyl]selenenyl selenocyanate (), with a stable Se-Se bond are described. The isolation of stable , both in the solid state and in solution, is facilitated by strong intramolecular SeN interaction. The compound , an example of unsymmetrical diselenide, did not exhibit any glutathione peroxidase-like activity. The reaction of with thiophenol afforded (3H-benzo[c][1,2]diselenol-3-yl)(phenyl)sulfane.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Crystallography, X-Ray
  • Cyanates / chemistry*
  • Glutathione Peroxidase / chemistry*
  • Glutathione Peroxidase / metabolism
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Organoselenium Compounds / chemistry*
  • Organoselenium Compounds / pharmacology*
  • Oxygen / chemistry
  • Phenols / chemistry*
  • Selenium Compounds / chemistry*
  • Sulfhydryl Compounds / chemistry*

Substances

  • Cyanates
  • Organoselenium Compounds
  • Phenols
  • Selenium Compounds
  • Sulfhydryl Compounds
  • selenocyanic acid
  • thiophenol
  • Glutathione Peroxidase
  • Oxygen