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Keywords:

  • NMR;
  • 77Se[BOND]1H spin–spin coupling constants;
  • SOPPA;
  • HMBC;
  • stereochemical analysis;
  • sterically crowded phenylselanylalkenes

Abstract

Stereochemical study of five sterically crowded phenylselanylalkenes obtained via the hydroselenation of either terminal or internal alkynes with benzeneselenol catalyzed by the nanosized Ni complexes has been carried out based on the experimental HMBC measurements and theoretical second order palarization propagator approach (SOPPA) calculations of their 77Se[BOND]1H spin–spin coupling constants across double bond in combination with the energy-based theoretical conformational analysis performed at the MP2/6-311G** level. It has been found that studied phenylselanylalkenes adopt mainly skewed s-cis conformation with the noticeable out-of-plane deviations of the phenylselanyl and phenyl groups. Copyright © 2011 John Wiley & Sons, Ltd.