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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.
Verfasserangaben: | 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 |
Titel des übergeordneten Werks (Englisch): | Tetrahedron |
Verlag: | Elsevier |
Verlagsort: | Oxford |
Publikationstyp: | Wissenschaftlicher Artikel |
Sprache: | Englisch |
Jahr der Erstveröffentlichung: | 2019 |
Erscheinungsjahr: | 2019 |
Datum der Freischaltung: | 06.10.2020 |
Freies Schlagwort / 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 |
Band: | 75 |
Ausgabe: | 46 |
Seitenanzahl: | 9 |
Fördernde Institution: | Ministry of Education and Science of the Russian FederationMinistry of Education and Science, Russian Federation |
Organisationseinheiten: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
DDC-Klassifikation: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Peer Review: | Referiert |