Can the −CF<sub>3</sub> Group Act as a Tight, Well-Defined Hydrogen Bond Acceptor? A Clear Crystallographic CF<sub>2</sub>–F···H–N<sup>+</sup> Interaction Says Yes
Muyuan Wang, Nathaniel G. Garrison, Phuong Minh Nguyen, Aarush Prasad, Yuang Wang, Hyeok-Kyu Kwon, Gina Kim, Maxime A. Siegler, Thomas Lectka
Abstract
The CF 3 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 CF 3 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.
Topics & Concepts
ChemistryHydrogen bondCrystallographyAcceptorGroup (periodic table)Intermolecular forceCrystal structureX-ray crystallographyStereochemistryMoleculeDiffractionPhysicsOrganic chemistryCondensed matter physicsOpticsFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsMolecular Spectroscopy and Structure