Conformational Analysis of 2-Formylselenophene by Means of 13C–1H, 13C–13C, and 77Se–1H Spin–Spin Coupling Constants

Yury Yu. Rusakov; Leonid B. Krivdin; Natalia V. Istomina; Ekaterina P. Levanova; Galina G. Levkovskaya

doi:10.1071/CH09010

RESEARCH ARTICLE

Conformational Analysis of 2-Formylselenophene by Means of ¹³C–¹H, ¹³C–¹³C, and ⁷⁷Se–¹H Spin–Spin Coupling Constants

Yury Yu. Rusakov ^A , Leonid B. Krivdin ^A ^B , Natalia V. Istomina ^A , Ekaterina P. Levanova ^A and Galina G. Levkovskaya ^A

+ Author Affiliations

- Author Affiliations

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

^B Corresponding author. Email: krivdin_office@irioch.irk.ru

Australian Journal of Chemistry 62(7) 734-738 https://doi.org/10.1071/CH09010
Submitted: 7 January 2009 Accepted: 4 February 2009 Published: 13 July 2009

Abstract

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.

Acknowledgements

Financial support from the Russian Foundation for Basic Research (Grant no. 08–03–00021) is acknowledged. L.B.K. thanks Professor Sauer for providing him with the extended aug-cc-pVTZ-J basis set including selenium.

References

Conformational Analysis of 2-Formylselenophene by Means of 13C–1H, 13C–13C, and 77Se–1H Spin–Spin Coupling Constants

Abstract

Acknowledgements

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Conformational Analysis of 2-Formylselenophene by Means of ¹³C–¹H, ¹³C–¹³C, and ⁷⁷Se–¹H Spin–Spin Coupling Constants