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

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-07, Vol.89 (13), p.9681-9685
Main Authors: Wang, Muyuan, Garrison, Nathaniel, Nguyen, Phuong Minh, Prasad, Aarush, Wang, Yuang, Kwon, Hyeok-Kyu, Kim, Gina, Siegler, Maxime A., Lectka, Thomas
Format: Article
Language:English
Subjects:
hydrogen
hydrogen bonding
organic chemistry
spectroscopy
X-ray diffraction
Online Access:Get full text
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Summary: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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c00873