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Fluorine as hydrogen bond acceptor: Experimental Evidence and Computational Calculations

Dalvit, Claudio and Invernizzi, Christian and Vulpetti, Anna (2014) Fluorine as hydrogen bond acceptor: Experimental Evidence and Computational Calculations. Chemistry A European Journal.

Abstract

Hydrogen bonding interactions play an important role in many chemical and biological systems. Fluorine acting as an hydrogen bond acceptor in intermolecular and intramolecular interactions has been the subject of many discussions and there are different opinions about it. Recently, we have proposed a correlation between the propensity of fluorine to be involved in hydrogen bond and its 19F NMR chemical shift. We now provide additional experimental and computational evidence for this correlation. The strength of hydrogen bond complexes involving fluorine moieties with diverse 19F NMR chemical shifts was measured and characterized in simple systems using three NMR parameters and compared to the well-known hydrogen bond complex formed between acetophenone and p-fluorophenol. Computed values of the molecular electrostatic potential at the different fluorine atoms and the analysis of the electron density topology at bond critical points correlate well with the NMR results.

Item Type: Article
Keywords: Fluorine, Hydrogen bond, Fluorine NMR spectroscopy, Fluorine NMR screening, molecular electrostatic potential, non-covalent interactions
Date Deposited: 13 Oct 2015 13:13
Last Modified: 13 Oct 2015 13:13
URI: https://oak.novartis.com/id/eprint/21254

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