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.

energy decomposition analysis

blue shifting

hydrogen bonding

electronegativity

Author

Chanan D. Sessler

Massachusetts Institute of Technology (MIT)

Martin Rahm

Cornell University

Sabine Becker

Massachusetts Institute of Technology (MIT)

Jacob M. Goldberg

Massachusetts Institute of Technology (MIT)

F. Wang

Massachusetts Institute of Technology (MIT)

Stephen J. Lippard

Massachusetts Institute of Technology (MIT)

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

Latest update

5/21/2021