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. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Graton, J., Wang, Z., Brossard, A. M., Gonçalves Monteiro, D., Le Questel, J. Y., & Linclau, B. (2012). An unexpected and significantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols. Angewandte Chemie - International Edition, 51(25), 6176–6180. https://doi.org/10.1002/anie.201202059
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