Structural trends of 77Se[BOND]1H spin–spin coupling constants and conformational behavior of 2-substituted selenophenes

Authors

  • Yury Yu. Rusakov,

    1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky St. 1, 664033 Irkutsk, Russia
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  • Leonid B. Krivdin,

    Corresponding author
    1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky St. 1, 664033 Irkutsk, Russia
    • A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky St. 1, 664033 Irkutsk, Russia.
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  • Stephan P. A. Sauer,

    1. Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100, Copenhagen Ø, Denmark
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  • Ekaterina P. Levanova,

    1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky St. 1, 664033 Irkutsk, Russia
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  • Galina G. Levkovskaya

    1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky St. 1, 664033 Irkutsk, Russia
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Abstract

Experimental measurements and second-order polarization propagator approach (SOPPA) calculations of 77Se[BOND]1H spin–spin coupling constants together with theoretical energy-based conformational analysis in the series of 2-substituted selenophenes have been carried out. A new basis set optimized for the calculation of 77Se[BOND]1H spin–spin coupling constants has been introduced by extending the aug-cc-pVTZ-J basis for selenium. Most of the spin–spin coupling constants under study, especially vicinal 77Se[BOND]1H couplings, demonstrated a remarkable stereochemical behavior with respect to the internal rotation of the substituent in the 2-position of the selenophene ring, which is of major importance in the stereochemical studies of the related organoselenium compounds. Copyright © 2009 John Wiley & Sons, Ltd.

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