Conformational analysis of N-phenyl- and N-trifyl-4,4-dimethyl-4-silathiane 1-sulfimides

  • N-Substituted 4,4-dimethyl-4-silathiane 1-sulfimides Me2Si(sic)S=NSO2R [R- Ph (1), CF3 (2)] were studied experimentally by variable temperature dynamic NMR spectroscopy. Low temperature 13 C NMR spectra of the two compounds revealed the frozen ring inversion process and approximately equal content of the axial and equatorial conformers. Calculations of the 4-silathiane derivatives 1, 2 and the model compound [R Me (3)] as well as their carbon analogs, the similarly N-substituted (sic)S=NSO2R thiane 1-sulfimides [R = Ph (4), CF3 (5), Me (6)] at the DFT/B3LYP/6-311G(d, p) level in the gas phase and in chloroform solution using the PCM model at the same level of theory showed a strong dependence of the relative stability of the conformer on the solvent. The electronegative trifluoromethyl group increases the relative stability of the axial conformer.

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Author:Bagrat A. Shainyan, Elena N. Suslova, Erich Kleinpeter
ISSN:0894-3230 (print)
Parent Title (English):Journal of physical organic chemistry
Place of publication:Malden
Document Type:Article
Year of first Publication:2011
Year of Completion:2011
Release Date:2017/03/26
Tag:4-silathianes; conformational analysis; dynamic NMR; quantum chemical calculations; sulfimides
First Page:698
Last Page:704
Funder:Russian Foundation for Basic Research [08-03-91954]; Deutsche Forschungsgemeinschaft [08-03-91954]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert