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Keywords:

  • NMR;
  • 77Se-1H spin-spin coupling constants;
  • SOPPA;
  • conformational analysis;
  • diastereotopic assignment;
  • thiaselenetane;
  • selenasilole;
  • thiaselenole;
  • thiaselenolane;
  • dihydrothiaselenine

Abstract

A combined theoretical and experimental study on the stereochemical behavior of 77Se-1H spin-spin coupling constants has been performed at the second-order polarization propagator approach level together with heteronuclear multiple-bond correlation technique in the series of selenium-containing four-, five- and six-membered heterocycles including the derivatives of thiaselenetane, selenasilole, thiaselenole, thiaselenolane and dihydrothiaselenine. Geminal and vicinal 77Se-1H spin-spin couplings were shown to have the pronounced stereochemical dependences in respect with the topology of the coupling pathway, internal rotation of the side-chain substituents and ring inversion providing a straightforward tool for the conformational analysis and diastereotopic assignments in the chiral organoselenium compounds. Copyright © 2011 John Wiley & Sons, Ltd.