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Manuskript_327N_ChemRxiv.pdf (1.32 MB)
Inter- and Intramolecular Aryl-Aryl-Interactions in Partially Fluorinated Ethylenedioxy-Bridged Bisarenes
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
submitted on 11.07.2020 and posted on 13.07.2020by Jan-Henrik Weddeling, Yury Vishnevskiy, Beate Neumann, Hans-Georg Stammler, Norbert W. Mitzel
Several ethylenedioxy-bridged bisarenes with a variety of
type and number of aryl groups were synthesized to study non-covalent dispersion-driven inter- and intramolecular aryl-aryl-interactions
in the solid state and gas phase. Intramolecular interactions are preferably found in the gas phase. DFT calculations of dispersion-corrected energy scans for rotations around the ethylenedioxy-bridge
and optimized structures show larger interacting aromatic groups to
increase the dispersion energy. Single molecule structures generally
adopt folded conformations with short intramolecular aryl-aryl-contacts. Gas electron diffraction experiments were performed exemplarily for 1-(pentafluorophenoxy)-2-(phenoxy)ethane. A new procedure
for structure refinement was developed to deal with the conformational complexity of such molecules. The results are an experimental
confirmation of the existence of folded conformations of this
molecule with short -intramolecular aryl-aryl distances in the gas
phase. Solid-state structures are dominated by stretched structures
without intramolecular aryl-aryl-interactions but interactions with