Conformational analysis and diastereotopic assignments in the series of selenium-containing heterocycles by means of 77Se-1H spin-spin coupling constants: a combined theoretical and experimental study
✍ Scribed by Yury Yu. Rusakov; Leonid B. Krivdin; Vladimir A. Potapov; Maxim V. Penzik; Svetlana V. Amosova
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- English
- Weight
- 319 KB
- Volume
- 49
- Category
- Article
- ISSN
- 0749-1581
- DOI
- 10.1002/mrc.2760
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✦ Synopsis
Abstract
A combined theoretical and experimental study on the stereochemical behavior of ^77^Se‐^1^H 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 ^77^Se‐^1^H 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.