Can the -CF3 Group Act as a Tight, Well-Defined Hydrogen Bond Acceptor? A Clear Crystallographic CF2-F···H-N+ Interaction Says Yes
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Updated: Jun 22, 2025

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Muyuan Wang1, Nathaniel Garrison1, Phuong Minh Nguyen1
1Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, Maryland 21218, United States.
Abstract:
The CF3 group is well noted for being noninteractive with other functional groups. In this Note, we present a highly rigid model system containing a significant hydrogen bonding interaction between a charged N-H donor and a CF3 acceptor that challenges this accepted wisdom. Spectroscopic and single crystal X-ray crystallography data characterize this interaction, consistent with a weak to moderate hydrogen bond that would be difficult to observe in an intermolecular system.
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