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σ-Hole Bonding: A Physical Interpretation

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Halogen Bonding I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 358))

Abstract

The anisotropic electronic densities of covalently-bonded Group IV–VII atoms frequently give rise to regions of positive electrostatic potential on the extensions of covalent bonds to these atoms. Through such positive “σ-holes,” the atoms can interact attractively and highly directionally with negative sites such as the lone pairs of Lewis bases, anions, π electrons, etc. In the case of Group VII this is called “halogen bonding.” Hydrogen bonding can be viewed as a less directional subset of σ-hole interactions. Since positive σ-holes often exist in conjunction with regions of negative potential, the atoms can also interact favorably with positive sites. In accordance with the Hellmann–Feynman theorem, all of these interactions are purely Coulombic in nature (which encompasses polarization and dispersion). The strength of σ-hole bonding increases with the magnitudes of the potentials of the positive σ-hole and the negative site; their polarizabilities must sometimes also be taken explicitly into account.

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Acknowledgements

This work was supported by the Deutsche Forschungsgemeinschaft as part of the Excellence Cluster “Engineering of Advanced Materials” and SFB953 “Synthetic Carbon Allotropes”.

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Authors and Affiliations

  1. Department of Chemistry, University of New Orleans, New Orleans, LA, 70148, USA

    Peter Politzer & Jane S. Murray

  2. CleveThcoComp, 1951 W. 26th Street, Cleveland, OH, 44113, USA

    Peter Politzer & Jane S. Murray

  3. Computer-Chemie-Centrum, Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Nägelsbachstrasse 25, 91052, Erlangen, Germany

    Timothy Clark

  4. Centre for Molecular Design, University of Portsmouth, King Henry Building, King Henry I Street, Portsmouth, PO1 2DY, UK

    Timothy Clark

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  1. Peter Politzer
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Correspondence to Peter Politzer .

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Editors and Affiliations

  1. Dipartimento di Chimica, Polytechnic University of Milan, Milano, Italy

    Pierangelo Metrangolo

  2. Dipartimento di Chimica, Polytechnic University of Milan, Milano, Italy

    Giuseppe Resnati

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Politzer, P., Murray, J.S., Clark, T. (2014). σ-Hole Bonding: A Physical Interpretation. In: Metrangolo, P., Resnati, G. (eds) Halogen Bonding I. Topics in Current Chemistry, vol 358. Springer, Cham. https://doi.org/10.1007/128_2014_568

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