4 years ago

CF2H, a Hydrogen Bond Donor

CF2H, a Hydrogen Bond Donor
Stephen J. Lippard, Martin Rahm, Sabine Becker, Fang Wang, Jacob M. Goldberg, Chanan D. Sessler
The CF2H group, a potential surrogate for the OH group, can act as an unusual hydrogen bond donor, as confirmed by crystallographic, spectroscopic, and computational methods. Here, we demonstrate the bioisosterism of the OH and CF2H groups and the important roles of CF2–H···O hydrogen bonds in influencing intermolecular interactions and conformational preferences. Experimental evidence, corroborated by theory, reveals the distinctive nature of CF2H hydrogen bonding interactions relative to their normal OH hydrogen bonding counterparts.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b04457

DOI: 10.1021/jacs.7b04457

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