Literature DB >> 28576078

CF2H, a Hydrogen Bond Donor.

Chanan D Sessler1, Martin Rahm2, Sabine Becker1, Jacob M Goldberg1, Fang Wang1, Stephen J Lippard1.   

Abstract

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.

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Year:  2017        PMID： 28576078      PMCID： PMC6535088          DOI： 10.1021/jacs.7b04457

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


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