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Directionality of intermolecular C–F···F–C interactions in crystals: experimental and theoretical charge density study

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Abstract

Bonding intermolecular F···F interactions were analyzed in crystal of a fluorinated benzene derivative using topological analysis of experimental charge density distribution. It was found that the values of electron density and potential energy density in bond critical points of the F···F interactions in crystal depended on the distance between the fluorine atoms, rather than on the corresponding C–F···F angles. The directionality of these F···F interactions was demonstrated by DFT-D and MP2 calculations for model hexafluorobenzene dimers. Possible discrepancies between dimerization energies computed by ab initio methods and via empirical correlations are discussed.

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Acknowledgments

This study was financially supported by Russian Science Foundation (Project 14-13-00884).

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Authors and Affiliations

  1. Higher Chemical College of the Russian Academy of Sciences, Miusskaya Sq, 9, 125190, Moscow, Russian Federation

    V. A. Karnoukhova

  2. A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova St. 28, 119991, Moscow, Russian Federation

    V. A. Karnoukhova, I. V. Fedyanin & K. A. Lyssenko

Authors
  1. V. A. Karnoukhova
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  2. I. V. Fedyanin
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  3. K. A. Lyssenko
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Correspondence to I. V. Fedyanin.

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Dedicated to the memory of Prof. Oleg V. Shishkin.

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Karnoukhova, V.A., Fedyanin, I.V. & Lyssenko, K.A. Directionality of intermolecular C–F···F–C interactions in crystals: experimental and theoretical charge density study. Struct Chem 27, 17–24 (2016). https://doi.org/10.1007/s11224-015-0622-8

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  • DOI: https://doi.org/10.1007/s11224-015-0622-8

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