Abstract
Three compounds with phenyl and pentafluorophenyl rings bridged by (CH2)3 and (CH2)2SiMe2 units were synthesized by hydrosilylation and C−C coupling reactions. Their solid-state structures are dominated by intermolecular π stacking interactions, primarily leading to dimeric or chain-type aggregates. Analysis of free molecules in the gas phase by electron diffraction revealed the most abundant conformer to be significantly stabilized by intramolecular π–π interactions. For the silicon compounds, structures characterized by σ–π interactions between methyl and pentafluorophenyl groups are second lowest in energy and cannot be excluded completely by the gas electron diffraction experiments. C6H5(CH2)3C6F5, in contrast, is present as a single conformer. The gas-phase structures served as a reference for the evaluation of a series of (dispersion-corrected) quantum-chemical calculations.
| Original language | English |
|---|---|
| Pages (from-to) | 13259-13263 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 56 |
| Issue number | 43 |
| DOIs | |
| Publication status | Published - 16 Oct 2017 |
| Externally published | Yes |
Funding
We thank Dr. Christian G. Reuter for maintenance of the gas electron diffractometer at Bielefeld University, Dipl.-Ing. Klaus-Peter Mester and Gerd Lipinski for recording NMR spectra, Heinz-Werner Patruck for measuring mass spectra, and Brigitte Michel for elemental analysis. We gratefully acknowledge financial support from the Deutsche For-schungsgemeinschaft through the SPP1807 (Mi477/28-1) and core facility GED@Bi (Mi477/35-1). Quantum-chemical calculations were carried out at the Paderborn Center for Parallel Computing (PC2).
| Funders | Funder number |
|---|---|
| Deutsche Forschungsgemeinschaft | Mi477/28-1, SPP1807, Mi477/35-1 |
