The fluorine atom is widely incorporated in bioactive compounds with the aim to improve their biological properties. This approach had great successes as shown by the number of fluorinated drugs on the market.1 In fact, the fluorination of an organic compound can significantly modify its physical properties. Among these, the hydrogen bond (H-bond) is one of the most important interactions which is implicated in the binding affinity of a drug with its biological target. The strong inductive effect of fluorine is generally considered to lead to an increase in hydrogen bond donating capacity of an adjacent hydrogen bond donor.3We have shown that this is not always the case for fluorohydrins and that a reduction in hydrogen bond donating capacity is also possible. This study demonstrates that the influence of fluorine is strongly dependent of the relative orientation between the fluorine atom and the hydroxyl group (see scheme below).3This presentation will give an overview of the recent results obtained, with a tentative rationale for the observed effects. References:1) a) K. M�ller, C. Faeh, F. Diederich, Science, 2007  , 317, 1881-1886, b) S. Purser, P. R. Moore, S. Swallow and V. Gouverneur, Chem. Soc. Rev., 2008  , 37, 320-330.2) 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.

Effect of fluorine introduction on hydrogen bond donating capacity of alcohols

248th National Meeting (2014)

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