CF2H, a Hydrogen Bond Donor
Journal article, 2017

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.. Exptl. evidence, corroborated by theory, reveals the distinctive nature of CF2H hydrogen bonding interactions relative to their normal OH hydrogen bonding counterparts.

electronegativity

energy decomposition analysis

blue shifting

hydrogen bonding

Author

Chanan D. Sessler

Martin Rahm

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Sabine Becker

Jacob M. Goldberg

F. Wang

Stephen J. Lippard

Journal of the American Chemical Society

0002-7863 (ISSN) 1520-5126 (eISSN)

Vol. 139 27 9325-9332

Subject Categories

Theoretical Chemistry

Organic Chemistry

DOI

10.1021/jacs.7b04457

PubMed

28576078

More information

Created

10/7/2017