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1-Methylthio-1-phenyl-1-silacyclohexane: Synthesis, conformational preferences in gas and solution by GED, NMR and theoretical calculations
- 1-Methylthio-1-phenyl-1-silacyclohexane 1, the first silacyclohexane with the sulfur atom at silicon, was synthesized and its molecular structure and conformational preferences studied by gas-phase electron diffraction (GED) and low temperature C-13 and Si-29 NMR spectroscopy (LT NMR). Quantum-chemical calculations were carried out both for the isolated species and solvate complexes in gas and in polar medium. The predominance of the 1-MeSaxPheq conformer in gas phase (1-Ph-eq :1-Ph-ax = 55:45, Delta G degrees = 0.13 kcal/mol) determined from GED is consistent with that measured in the freon solution by LT NMR (1-Ph-eq:1-Ph-ax = 65:35, Delta G degrees = 0.12 kcal/mol), the experimentally measured ratios being close to that estimated by quantum chemical calculations at both the DFT and MP2 levels of theory. (C) 2019 Elsevier Ltd. All rights reserved.
Author details: | Bagrat A. ShainyanORCiD, Elena N. Suslova, Tran Dinh Phien, Sergey A. ShlykovORCiD, Matthias HeydenreichORCiD, Erich KleinpeterORCiDGND |
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DOI: | https://doi.org/10.1016/j.tet.2019.130677 |
ISSN: | 0040-4020 |
Title of parent work (English): | Tetrahedron |
Publisher: | Elsevier |
Place of publishing: | Oxford |
Publication type: | Article |
Language: | English |
Year of first publication: | 2019 |
Publication year: | 2019 |
Release date: | 2020/10/06 |
Tag: | 1-Methylthio-1-phenyl-1-silacyclohexane; Conformational analysis; DFT and MP2 calculations; Gas phase electron diffraction; Low-temperature C-13 and Si-29 NMR |
Volume: | 75 |
Issue: | 46 |
Number of pages: | 9 |
Funding institution: | Ministry of Education and Science of the Russian FederationMinistry of Education and Science, Russian Federation |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Peer review: | Referiert |