While theory unambiguously supports the existence of hydrogen bonds to the fluorine atom in fluoroorganics, experimentally the evidence is less clear.  Specifically, only intramolecular hydrogen bonds to fluorine are seen, and even this result is contested.  In this paper, two methods are used to measure the strength of intramolecular hydrogen bonds with fluorine. One method is high level computational work. The second is an NMR method, whereby the compound to be studied is titrated with a weak Lewis base such as CH3CN. This experiment is also run as a competition experiment with a suitable model compound. Compounds studied include the 2-fluoro derivatives of phenol, aniline, and acetanilide.

On the strength of intramolecular hydrogen bonds to fluorine: Theory and experiment

247th National Meeting (2014)

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