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. Crown Copyright 2012 Published by Elsevier B.V. All rights reserved.
| Original language | English |
|---|---|
| Pages (from-to) | 115-120 |
| Number of pages | 6 |
| Journal | Journal of Molecular Structure |
| Volume | 1036 |
| DOIs | |
| Publication status | Published - 27-Mar-2013 |
Keywords
- Heterocyclic compounds
- Organic synthesis
- Conformational analysis
- Crystal structure
- MP2 calculations
- OFT calculations
- END-CAPPED OLIGO(CYCLOHEXYLIDENES)
- INTRAMOLECULAR CHARGE SEPARATION
- BOND ORBITAL ANALYSES
- INITIO SCF-MO
- ELECTRON-DIFFRACTION
- SPECTROSCOPY
- CONFORMATIONS
- BICYCLOPROPYL
- BICYCLOHEXYL
- DEPENDENCE
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CCDC 859046: Experimental Crystal Structure Determination
Van Walree, C. A. (Contributor), Lutz, M. (Contributor), Spek, A. L. (Contributor), Jenneskens, L. W. (Contributor) & Havenith, R. (Contributor), University of Groningen, 16-Dec-2011
DOI: 10.5517/ccxtx5s
Dataset