1. Molecular and solid state structure of 4,4 '-bis(tetrahydrothiopyranyl)
- Author
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van Walree, C.A., Lutz, M., Spek, A.L., Jenneskens, L.W., Havenith, R.W.A., Chemical education, Crystal and Structural Chemistry, Organic Chemistry and Catalysis, Rontgen participation programme, Sub Practicum, Sub Crystal and Structural Chemistry, Sub Chem Biol & Organic Chem begr 1-6-12, Sub NMR Spectroscopy, and Zernike Institute for Advanced Materials
- Subjects
Diffraction ,INTRAMOLECULAR CHARGE SEPARATION ,OFT calculations ,Organic synthesis ,BICYCLOHEXYL ,Crystal structure ,END-CAPPED OLIGO(CYCLOHEXYLIDENES) ,ELECTRON-DIFFRACTION ,Analytical Chemistry ,MP2 calculations ,Inorganic Chemistry ,BOND ORBITAL ANALYSES ,chemistry.chemical_compound ,CONFORMATIONS ,DEPENDENCE ,Alkane stereochemistry ,Molecule ,Spectroscopy ,INITIO SCF-MO ,SPECTROSCOPY ,Chemistry ,Organic Chemistry ,Crystallography ,Conformational analysis ,Electron diffraction ,Heterocyclic compounds ,BICYCLOPROPYL ,Single crystal - 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.
- Published
- 2013
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