Synthesis and Structural Diversity of Triaryl(phenylethyl)silanes

Linnemannstöns M, Neumann B, Stammler H-G, Mitzel NW (2020)
SYNTHESIS-STUTTGART 52(7): 1025-1034.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Starting from trichloro(phenylethyl)silane, six differently fluorinated triaryl(phenylethyl)silanes were synthesized by salt elimination reactions and their structures were determined by X-ray diffraction analysis. Tris(pentafluorophenyl)(phenylethyl)silane reveals a folded structure due to intramolecular pi-stacking interactions, while those with a lower degree of fluorination show either intermolecular pi-stacking or no interplay between the aryl groups. A similar folded structure was observed for (4-methylphenethyl)tris(pentafluorophenyl)silane and [2-(naphth-2-yl)ethyl]tris(pentafluorophenyl)silane, both generated from the corresponding trichlorosilanes. In contrast, the inversely fluorinated [2-(pentafluorophenyl)ethyl]triphenylsilane only revealed intermolecular pi-stacking interactions. Compounds with tetrafluoropyridyl substituents behave differently; with these compounds, pi-stacking is only observed between the fluorinated units. All compounds were analyzed by NMR and IR spectroscopy, elemental analyses and single-crystal X-ray diffraction, and found to have strong H/C/N/F center dot center dot center dot F and N center dot center dot center dot C contacts.
Stichworte
inter; intramolecular pi-stacking; solid-state structures; London; dispersion; bridged arenes; fluorinated arenes
Erscheinungsjahr
2020
Zeitschriftentitel
SYNTHESIS-STUTTGART
Band
52
Ausgabe
7
Seite(n)
1025-1034
ISSN
0039-7881
eISSN
1437-210X
Page URI
https://pub.uni-bielefeld.de/record/2943309

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Linnemannstöns M, Neumann B, Stammler H-G, Mitzel NW. Synthesis and Structural Diversity of Triaryl(phenylethyl)silanes. SYNTHESIS-STUTTGART. 2020;52(7):1025-1034.
Linnemannstöns, M., Neumann, B., Stammler, H. - G., & Mitzel, N. W. (2020). Synthesis and Structural Diversity of Triaryl(phenylethyl)silanes. SYNTHESIS-STUTTGART, 52(7), 1025-1034. doi:10.1055/s-0039-1690785
Linnemannstöns, M., Neumann, B., Stammler, H. - G., and Mitzel, N. W. (2020). Synthesis and Structural Diversity of Triaryl(phenylethyl)silanes. SYNTHESIS-STUTTGART 52, 1025-1034.
Linnemannstöns, M., et al., 2020. Synthesis and Structural Diversity of Triaryl(phenylethyl)silanes. SYNTHESIS-STUTTGART, 52(7), p 1025-1034.
M. Linnemannstöns, et al., “Synthesis and Structural Diversity of Triaryl(phenylethyl)silanes”, SYNTHESIS-STUTTGART, vol. 52, 2020, pp. 1025-1034.
Linnemannstöns, M., Neumann, B., Stammler, H.-G., Mitzel, N.W.: Synthesis and Structural Diversity of Triaryl(phenylethyl)silanes. SYNTHESIS-STUTTGART. 52, 1025-1034 (2020).
Linnemannstöns, Marvin, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. “Synthesis and Structural Diversity of Triaryl(phenylethyl)silanes”. SYNTHESIS-STUTTGART 52.7 (2020): 1025-1034.