Molecular and solid state structure of 4,4'-bis(tetrahydrothiopyranyl)

Cornelis van Walree, Martin Lutz, Anthony Spek, Leonardus Jenneskens, Remco Havenith

    Research output: Contribution to journalArticlepeer-review

    1 Citation (Scopus)

    Abstract

    Single crystal X-ray diffraction reveals that 4,4′- bis(tetrahydrothiopyranyl) crystallizes in an equatorial-equatorial geometry with a gauche conformation along the central carbon-carbon bond. B3LYP/6-311G** and MP2/6-311G** calculations show that the antiperiplanar conformation is higher in energy than the gauche one because of sulfur induced stretching and widening of the cyclohexane-like rings. Calculations at various levels of theory suggest that in the antiperiplanar region the twisting coordinate of 4,4′- bis(tetrahydrothiopyranyl) exhibits a very shallow double-well potential. The gauche molecular structure of 4,4′-bis(tetrahydrothiopyranyl) thwarts efficient packing of its molecules in the solid state.

    Original languageEnglish
    Pages (from-to)115-120
    Number of pages6
    JournalJournal of Molecular Structure
    Volume1036
    DOIs
    Publication statusPublished - 27 Mar 2013

    Keywords

    • Conformational analysis
    • Crystal structure
    • DFT calculations
    • Heterocyclic compounds
    • MP2 calculations
    • Organic synthesis

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