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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Intermolecular Aliphatic C-F···H-C Interaction in the Presence of "Stronger" Hydrogen Bond Acceptors:
Cody Ross Pitts1, Maxime A Siegler1, Thomas Lectka1
1Department of Chemistry, Johns Hopkins University , 3400 North Charles Street, Baltimore, Maryland 21218, United States.
Abstract:
An unprecedented intermolecular aliphatic C-F···H-C interaction was observed in the X-ray crystal structure of a fluorinated triterpenoid. Despite the notion of fluorine being a poor acceptor, computational and IR studies revealed this interaction to be a weak to moderate hydrogen bond with a C-H stretch vibration frequency blue-shifted by 14 cm-1 and d(F-H) = 2.13 Å. In addition, the aliphatic C-F bond is the preferred acceptor in the presence of multiple, traditionally stronger oxygen-based hydrogen bond acceptors.
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