An unexpected and significantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols. [VIP paper]

An unexpected and significantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols. [VIP paper]

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...

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Bibliographic Details
Main Authors: Graton, Jérôme (Author), Wang, Zhong (Author), Brossard, Anne-Marie (Author), Gonçalves Monteiro, Daniela (Author), Le Questel, Jean-Yves (Author), Linclau, Bruno (Author)
Format: Article
Language:English
Published: 2012-06-18.
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Summary: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.

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