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Updated: Oct 4, 2025

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Published on: July 27, 2022
Spectroscopic and Crystallographic Characterization of the R3 N+ -C-H⋅⋅⋅X Interaction
Joseph N Capilato1, Stefan A Harry1, Maxime A Siegler1
1Department of Chemistry, Johns Hopkins University, 3400 N Charles Street, Baltimore, MD 21218, USA.
Abstract:
As appreciation for nonclassical hydrogen bonds has progressively increased, so have efforts to characterize these interesting interactions. Whereas several kinds of C-H hydrogen bonds have been well-studied, much less is known about the R3 N+ -C-H⋅⋅⋅X variety. Herein, we present crystallographic and spectroscopic evidence for the existence of these interactions, with special relevance to Selectfluor chemistry. Of particular note is the propensity for Lewis bases to engage in nonclassical hydrogen bonding over halogen bonding with the electrophilic F atom of Selectfluor. Further, the first examples of 1 H NMR experiments detailing R3 N+ -C-H⋅⋅⋅X (X=O, N) hydrogen bonds are described.
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