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J Am Chem Soc. 2017 Jul 12;139(27):9325-9332. doi: 10.1021/jacs.7b04457. Epub 2017 Jun 27.

CF2H, a Hydrogen Bond Donor.

Author information

1
Department of Chemistry, Massachusetts Institute of Technology , 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
2
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University , Ithaca, New York 14853, United States.

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.

PMID:
28576078
PMCID:
PMC6535088
DOI:
10.1021/jacs.7b04457
[Indexed for MEDLINE]
Free PMC Article

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