Structural Characterization of Hydro-, Chloro- and Fluoroorganylsilanes with Substituents of Varying Electron Withdrawing Character

Keßler M, Porath S, Stammler H-G, Hoge B (2021)
European journal of inorganic chemistry (10): 907-913.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
We report on the molecular structure of trimethylsilanes Si(CH3)(3)X in which the substituents X, namely (Z)-pentafluoropropen-1-yl, trifluoropropyn-1-yl, pentafluoroethyl, trifluorovinyl, vinyl, propyn-1-yl, di- and trichloromethyl, display electron withdrawing effects of varying strength. The lengths of the bonds between the silicon and the carbon atoms of X correlate with the hybridization of the respective orbitals and the steric demand of X rather than with the electron withdrawing capability. In case of chlorinated substituents dispersion effects seem to shorten the Si-C bond. Furthermore, a route for generating trifluoropropyn-1-yllithium from the cryogen 2,3,3,3-tetrafluoropropene (HFO-1234yf) and n-butyllithium is described. Tetrafluoropropen-1-yllithium is slowly formed at -80 degrees C but even at this temperature spontaneous elimination of LiF occurs. Deprotonation of the formed 3,3,3-trifluoropropyne requires temperatures of above -60 degrees C leading to trifluoropropyn-1-yllithium which appears as relatively stable at room temperature.
Stichworte
Chloroorganylsilanes; Fluoroorganylsilanes; Structure elucidation; Substituent effects; Trifluoropropynyllithium groups; Trimethylsilanes
Erscheinungsjahr
2021
Zeitschriftentitel
European journal of inorganic chemistry
Ausgabe
10
Seite(n)
907-913
ISSN
1434-1948
eISSN
1099-0682
Finanzierungs-Informationen
Open-Access-Publikationskosten wurden durch die Universität Bielefeld im Rahmen des DEAL-Vertrags gefördert.
Page URI
https://pub.uni-bielefeld.de/record/2950679

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Keßler M, Porath S, Stammler H-G, Hoge B. Structural Characterization of Hydro-, Chloro- and Fluoroorganylsilanes with Substituents of Varying Electron Withdrawing Character. European journal of inorganic chemistry. 2021;(10):907-913.
Keßler, M., Porath, S., Stammler, H. - G., & Hoge, B. (2021). Structural Characterization of Hydro-, Chloro- and Fluoroorganylsilanes with Substituents of Varying Electron Withdrawing Character. European journal of inorganic chemistry(10), 907-913. https://doi.org/10.1002/ejic.202001065
Keßler, M., Porath, S., Stammler, H. - G., and Hoge, B. (2021). Structural Characterization of Hydro-, Chloro- and Fluoroorganylsilanes with Substituents of Varying Electron Withdrawing Character. European journal of inorganic chemistry, 907-913.
Keßler, M., et al., 2021. Structural Characterization of Hydro-, Chloro- and Fluoroorganylsilanes with Substituents of Varying Electron Withdrawing Character. European journal of inorganic chemistry, (10), p 907-913.
M. Keßler, et al., “Structural Characterization of Hydro-, Chloro- and Fluoroorganylsilanes with Substituents of Varying Electron Withdrawing Character”, European journal of inorganic chemistry, 2021, pp. 907-913.
Keßler, M., Porath, S., Stammler, H.-G., Hoge, B.: Structural Characterization of Hydro-, Chloro- and Fluoroorganylsilanes with Substituents of Varying Electron Withdrawing Character. European journal of inorganic chemistry. 907-913 (2021).
Keßler, Mira, Porath, Sven, Stammler, Hans-Georg, and Hoge, Berthold. “Structural Characterization of Hydro-, Chloro- and Fluoroorganylsilanes with Substituents of Varying Electron Withdrawing Character”. European journal of inorganic chemistry 10 (2021): 907-913.
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2021-03-15T09:29:09Z
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