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              <p>Hydrogen bonding is the most important noncovalent interaction involved in molecular binding events. Herein, how γ ‐fluorination alters the hydrogen bond (HB)‐donating capacities of aliphatic alcohol groups is described. Herein, it is shown that the increase in HB‐donating capacity due to the fluorine electronegativity can be significantly attenuated by 6‐membered F•••HO intramolecular HB (IMHB), to the point where even in acyclic structures a decrease in alcohol HB‐donating capacity is observed. The correlation of experimental HB‐donating capacities (p K AHY ‐scale) with an easily computed descriptor, the Kenny molecular electrostatic potential V α (r), is discussed. It is shown that F•••HO IMHB leads to a V α (r) reduction which, in the case of highly populated IMHB conformers, leads to an underestimation of HB‐donating capacities. The use of conformational electrostatic potentials, however, was found to be very useful to describe OH•••F IMHB, as well as to explain variations in experimental alcohol HB‐donating capacities. Notably, V α (r)‐analysis allowed the identification of the importance of conformational equilibria in explaining HB‐donating capacity variations of identical fluorohydrin motifs, and notably it also reveals a cooperative effect involving a difluoromethyl group (CF 2 H) on alcohol HB‐donating capacity.</p>
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