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An Unexpected and Significantly Lower Hydrogen‐Bond‐Donating Capacity of Fluorohydrins Compared to Nonfluorinated Alcohols
Author(s) -
Graton Jérôme,
Wang Zhong,
Brossard AnneMarie,
Gonçalves Monteiro Daniela,
Le Questel JeanYves,
Linclau Bruno
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201202059
Subject(s) - intramolecular force , chemistry , alcohol , hydrogen bond , vicinal , fluorine , medicinal chemistry , inductive effect , organic chemistry , molecule
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.