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Aryl–Aryl Interactions in (Aryl‐Perhalogenated) 1,2‐Diaryldisilanes
Author(s) -
Linnemannstöns Marvin,
Schwabedissen Jan,
Neumann Beate,
Stammler HansGeorg,
Berger Raphael J. F.,
Mitzel Norbert W.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905727
Subject(s) - aryl , intramolecular force , chemistry , molecule , conformational isomerism , crystallography , stereochemistry , solid state , london dispersion force , salt (chemistry) , medicinal chemistry , organic chemistry , alkyl , van der waals force
Three 1,2‐diaryltetramethyldisilanes X 5 C 6 ‐(SiMe 2 ) 2 ‐C 6 X 5 with two C 6 H 5 , C 6 F 5 , or C 6 Cl 5 groups were studied concerning the importance of London dispersion driven interactions between their aryl groups. They were prepared from 1,2‐dichlorotetramethyldisilane by salt elimination. Their structures were determined in the solid state by X‐ray diffraction and for free molecules by gas electron‐diffraction. The solid‐state structures of the fluorinated and chlorinated derivatives are dominated by aryl–aryl interactions. Unexpectedly, Cl 5 C 6 ‐(SiMe 2 ) 2 ‐C 6 Cl 5 exists exclusively as an eclipsed syn ‐conformer in the gas phase with strongly distorted Si‐C 6 Cl 5 units due to strong intramolecular interactions. In contrast, F 5 C 6 ‐(SiMe 2 ) 2 ‐C 6 F 5 reveals weaker interactions. The contributions to the total interaction energy were analyzed by SAPT calculations.