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Following Halogen Bonds Formation with Bader’s Atoms-in-Molecules Theory

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Applications of Topological Methods in Molecular Chemistry

Part of the book series: Challenges and Advances in Computational Chemistry and Physics ((COCH,volume 22))

Abstract

In this chapter. we will show how Bader’s atoms-in-molecules theory enables to unravel the main physicochemical factors that drive the formation of halogen bonds, which are intriguing and fascinating noncovalent interactions at work as well as in crystals, biological and chemical systems, and which have found numerous applications in, among other fields, drug design and supramolecular chemistry. In particular, the use of Pendás and coworkers’ interacting quantum atoms scheme will cast the light on the nature of such interactions (more or less electrostatic, more or less covalent) and will provide useful hints to account for the existence or absence of energy minima in the corresponding potential energy surface. Importantly, such a rationalizing approach can be carried out whatever the system and also possesses predictive power.

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Notes

  1. 1.

    Very small negative values for large separation distances are due to basis set superposition errors.

  2. 2.

    It is fundamental to notice that this critical point is a BCP at the equilibrium geometry for the chlorine and bromine complexes, while no BCP is present along the fluorine pathway since it does not feature any equilibrium geometry.

  3. 3.

    We use this partner instead of NH3 because, with ammonia, the creation of a F…H–N hydrogen bond is largely favoured; besides, the F2…NCCH3 complex has been already studied by Politzer and coworkers [109], so that comparisons of the different theoretical approaches are possible.

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Acknowledgements

V.T. and L.J. gratefully acknowledge the CRIHAN computational centre for providing computational resources, the Centre National de la Recherche Scientifique (CNRS) for a “Chaire d’Excellence” at the University of Rouen, and the Labex SynOrg (ANR-11-LABX-0029).

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  1. Normandy University, COBRA UMR 6014 & FR 3038, Université de Rouen, INSA Rouen, CNRS, 1 rue Tesniére, 76821, Cedex, Mont St Aignan, France

    Vincent Tognetti & Laurent Joubert

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  1. Vincent Tognetti
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  2. Laurent Joubert
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Correspondence to Vincent Tognetti or Laurent Joubert .

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Editors and Affiliations

  1. LCC-CNRS, Toulouse, France

    Remi Chauvin

  2. LCC-CNRS, Toulouse, France

    Christine Lepetit

  3. Théorique, UMR 761, Laboratoire de Chimie, Paris, France

    Bernard Silvi

  4. CNRS/UPM, MONARIS UMR 8233 (LADIR + LM2N), Paris, France

    Esmail Alikhani

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Tognetti, V., Joubert, L. (2016). Following Halogen Bonds Formation with Bader’s Atoms-in-Molecules Theory. In: Chauvin, R., Lepetit, C., Silvi, B., Alikhani, E. (eds) Applications of Topological Methods in Molecular Chemistry. Challenges and Advances in Computational Chemistry and Physics, vol 22. Springer, Cham. https://doi.org/10.1007/978-3-319-29022-5_16

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