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CF2H, a Hydrogen Bond Donor.

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.

SUBMITTER: Sessler CD 

PROVIDER: S-EPMC6535088 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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CF<sub>2</sub>H, a Hydrogen Bond Donor.

Sessler Chanan D CD   Rahm Martin M   Becker Sabine S   Becker Sabine S   Goldberg Jacob M JM   Wang Fang F   Lippard Stephen J SJ  

Journal of the American Chemical Society 20170627 27

The CF<sub>2</sub>H 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 CF<sub>2</sub>H groups and the important roles of CF<sub>2</sub>-H···O hydrogen bonds in influencing intermolecular interactions and conformational preferences. Experimental evidence, corroborated by theory, reveals the distinctive nature of CF<sub>2</sub>H hyd  ...[more]

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