Computational study of the anomeric effect in 2-[(4-substituted phenyl)seleno]-1,3-dithianes

Nurcan Şenyurt, Viktorya Aviyente*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


The conformational equilibrium of 1,3-dithiane-2-selenol and 2-[(4-substituted phenyl)seleno]-1,3-dithianes with NO2, H, CH3, OCH3 and N(CH3)2 as substituents has been studied with PM3 and HF/6-31G*. Both methods confirm the preference for the axial conformers for these compounds with electron witdrawing groups enhancing this trend. The structural parameters have been used to assess the presence of the endo and exo anomeric effects in the axial conformers. NBO analysis for 1,3-dithiane-2-selenol has shown that delocalization involving the sulfur and selenium lone pairs and the C2-Se anti-bonding orbital plays a role in stabilizing the axial conformer for this compound. Single point energy calculations in solution with HF/6-31G*//HF/6-31G* mimic the experimental results to a great extent.

Original languageEnglish
Pages (from-to)1463-1470
Number of pages8
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number7
Publication statusPublished - 1997
Externally publishedYes


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