Experimental measurements and second-order polarization propagator approach (SOPPA) calculations of (77)Se-(1)H 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 (77)Se-(1)H 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 (77)Se-(1)H 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.
Theoretical energy-based conformational analysis of 2-formylselenophene performed at the MP2/6–311G** level together with experimental measurements and SOPPA/aug-cc-pVTZ-J calculations of its 13C–1H, 13C–13C, and 77Se–1H spin–spin coupling constants showed that this compound predominantly adopts the s-cis conformation. Most of the spin–spin coupling constants under study, especially vicinal 77Se–1H couplings, demonstrate remarkable stereochemical behaviour with respect to the internal rotation of the formyl group, which is of major importance in stereochemical studies of the related selenium-containing compounds.
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