An Unexpected and Significantly Lower Hydrogen‐Bond‐Donating Capacity of Fluorohydrins Compared to Nonfluorinated Alcohols

Abstract

Rewriting the rules as fluorination does not always increase hydrogen-bond acidity: while the strongly electron-withdrawing fluorine significantly enhances alcohol H-bond acidity in anti-vicinal fluorohydrins, an intramolecular F???HO interaction overrules completely the inductive effect. This leads to an overall decrease in alcohol H-bond acidity, compared to the corresponding nonfluorinated alcohol.