The hydrogen bond (H-bond) is an important specific interaction between a molecule and its local environment.1 Given the strong electrostatic contribution to the overall energy of a hydrogen-bond, the introduction of a small and highly electronegative fluorine atom is expected to significantly increase the H-bond acidity of an adjacent H-bond donor.2We have shown on fluorohydrins that a OH-F interaction can occur and in that case, can strongly decrease the hydrogen bond donating capacity of the alcohol.3 One question arises from these observations: does this interaction persists when a competitive hydrogen bond donor is added?This presentation will give an overview of the recent results obtained on H-bond acidity of fluorohydrins, and NMR experiments to characterise the obtained structures. References:1) a) S. J. Grabowski, Chem. Rev., 2011 , 111, 2597; b) T. Steiner, Angew. Chem. Int. Ed., 2002 , 41, 48�76; c) C. Laurence et al., J. Med. Chem., 2009 , 52, 4073-4086.2) B. E. Smart, J. Fluorine Chem.,2001 , 109, 3-11.3) J. Graton, Z. Wang, A.-M. Brossard, D. Goncalves Monteiro, J.-Y. Le Questel, B. Linclau, Angew. Chem. Int. Ed., 2012 , 51, 6176-6180.

Observation on how intramolecular hydrogen bonding of alcohol with fluorine affects its intermolecular hydrogen bonding with acceptors

248th National Meeting (2014)

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