On the Nature of Improper Hydrogen Bonding in RCH₂F and RCHF₂ Motifs.

ABSTRACT: The RCH₂F and RCHF₂ groups are substituents of interest in medicinal and agrochemicals products. They have a polar aspect relative to the methyl (RCH₃) or trifluoromethyl (RCF₃) groups which results in a lowering of Log P's (water affinity). Here we use a computational approach to explore the nature of the interaction between RCH₂F and RCHF₂ in methanes and ethanes with chloride ion (and water), as a hydrogen bonding acceptor. A key observation is that the hydrogen atoms geminal to the fluorine(s) become less positively charged with increasing fluorination, a trend anticipated to weaken, not strengthen, their hydrogen bonding interactions. However this study demonstrates a dominating role for the electrostatic interaction of

SUBMITTER: Piscelli BA 

PROVIDER: S-EPMC12790382 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature