Pentafluoroethyl-substituted alpha-silanes: model compounds for new insights

Waerder B, Steinhauer S, Bader J, Neumann B, Stammler H-G, Vishnevskiy Y, Hoge B, Mitzel NW (2015)
Dalton Transactions 44(29): 13347-13358.

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Abstract
To further investigate the alpha-effect in silanes bearing a geminal donor atom, the model compounds (C2F5)(3)SiCH2NMe2, (C2F5)(3)SiCH2OMe and (C2F5)(3)SiONMe2 were prepared by introduction of pentafluoroethyl groups via nucleophilic substitution of the corresponding chloro-derivatives with pentafluoroethyl lithium. The substances were characterised by NMR spectroscopy and X-ray diffraction via in situ crystallization techniques. The solid state structures of these highly electronegatively substituted a-silanes contain monomeric molecules. The Si-C-N angle in (C2F5)(3)SiCH2NMe2 shows a value of 115.3(2)degrees and the Si-C-O angle in (C2F5)(3)SiCH2OMe a value of 105.4(1)degrees. Both values are smaller than the Si-C-C angle of the reference compound (C2F5)(3)SiCH2CH3 with a value of 118.6(2)degrees indicating attractive interaction between the silicon atom and the respective donor atoms. The Si-O-N angle in (C2F5)(3)SiONMe2 is extremely narrow at 82.0(1)degrees. This behaviour was further investigated by gas electron diffraction and by quantum-chemical calculations. The NBO method finds no significant orbital interactions between Si and N/O atoms in the Si-C-N, Si-C-O and Si-O-N units. The IQA model describes the compounds as strongly stabilised by electrostatic interactions between formally non-bonded silicon and donor atoms.
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Waerder B, Steinhauer S, Bader J, et al. Pentafluoroethyl-substituted alpha-silanes: model compounds for new insights. Dalton Transactions. 2015;44(29):13347-13358.
Waerder, B., Steinhauer, S., Bader, J., Neumann, B., Stammler, H. - G., Vishnevskiy, Y., Hoge, B., et al. (2015). Pentafluoroethyl-substituted alpha-silanes: model compounds for new insights. Dalton Transactions, 44(29), 13347-13358.
Waerder, B., Steinhauer, S., Bader, J., Neumann, B., Stammler, H. - G., Vishnevskiy, Y., Hoge, B., and Mitzel, N. W. (2015). Pentafluoroethyl-substituted alpha-silanes: model compounds for new insights. Dalton Transactions 44, 13347-13358.
Waerder, B., et al., 2015. Pentafluoroethyl-substituted alpha-silanes: model compounds for new insights. Dalton Transactions, 44(29), p 13347-13358.
B. Waerder, et al., “Pentafluoroethyl-substituted alpha-silanes: model compounds for new insights”, Dalton Transactions, vol. 44, 2015, pp. 13347-13358.
Waerder, B., Steinhauer, S., Bader, J., Neumann, B., Stammler, H.-G., Vishnevskiy, Y., Hoge, B., Mitzel, N.W.: Pentafluoroethyl-substituted alpha-silanes: model compounds for new insights. Dalton Transactions. 44, 13347-13358 (2015).
Waerder, Benedikt, Steinhauer, Simon, Bader, Julia, Neumann, Beate, Stammler, Hans-Georg, Vishnevskiy, Yury, Hoge, Berthold, and Mitzel, Norbert W. “Pentafluoroethyl-substituted alpha-silanes: model compounds for new insights”. Dalton Transactions 44.29 (2015): 13347-13358.
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