Halogen Bonding in Solution

  • Anna-Carin C. Carlsson
  • Alberte X. Veiga
  • Máté ErdélyiEmail author
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 359)


Because of its expected applicability for modulation of molecular recognition phenomena in chemistry and biology, halogen bonding has lately attracted rapidly increasing interest. As most of these processes proceed in solution, the understanding of the influence of solvents on the interaction is of utmost importance. In addition, solution studies provide fundamental insights into the nature of halogen bonding, including, for example, the relative importance of charge transfer, dispersion, and electrostatics forces. Herein, a selection of halogen bonding literature is reviewed with the discussion focusing on the solvent effect and the electronic characteristics of halogen bonded complexes. Hence, charged and neutral systems together with two- and three-center bonds are presented in separate sub-sections. Solvent polarity is shown to have a slight stabilizing effect on neutral, two-center halogen bonds while strongly destabilizes charged, two-center complexes. It does not greatly influence the geometry of three-center halogen bonds, even though polar solvents facilitate dissociation of the counter-ion of charged three-center bonds. The charged three-center bonds are strengthened by increased environment polarity. Solvents possessing hydrogen bond donor functionalities efficiently destabilize all types of halogen bonds, primarily because of halogen vs hydrogen bond competition. A purely electrostatic model is insufficient for the description of halogen bonds in polar systems whereas it may give reasonable correlation to experimental data obtained in noninteracting, apolar solvents. Whereas dispersion plays a significant role for neutral, two-center halogen bonds, charged halogen bond complexes possess a significant charge transfer characteristic.


Halogen bond Solution Solvation Solvent effect 



The research leading to these results has received funding from the European Union Seventh Framework Programme (FP7/2007–2013) under grant agreement no. 259638, and from the Swedish Research Council (VR 2012–3819). Jenny Mattsson (University of Gothenburg) is gratefully acknowledged for linguistic improvement of the text.


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Authors and Affiliations

  • Anna-Carin C. Carlsson
    • 1
  • Alberte X. Veiga
    • 1
  • Máté Erdélyi
    • 1
    Email author
  1. 1.Department of Chemistry and Molecular BiologyGothenburg UniversityGothenburgSweden

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