Halogen Bond: A Long Overlooked Interaction

  • Gabriella CavalloEmail author
  • Pierangelo Metrangolo
  • Tullio Pilati
  • Giuseppe Resnati
  • Giancarlo Terraneo
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 358)


Because of their high electronegativity, halogen atoms are typically considered, in most of their derivatives, as sites of high electron density and it is commonly accepted that they can form attractive interactions by functioning as the electron donor site (nucleophilic site). This is the case when they work as hydrogen bond acceptor sites. However, the electron density in covalently bound halogens is anisotropically distributed. There is a region of higher electron density, accounting for the ability of halogens to function as electron donor sites in attractive interactions, and a region of lower electron density where the electrostatic potential is frequently positive (mainly in the heavier halogens). This latter region is responsible for the ability of halogen atoms to function as the electron-acceptor site (electrophilic site) in attractive interactions formed with a variety of lone pair-possessing atoms, anions, and π-systems. This ability is quite general and is shown by a wide diversity of halogenated compounds (e.g., organohalogen derivatives and dihalogens). According to the definition proposed by the International Union of Pure and Applied Chemistry, any attractive interactions wherein the halogen atom is the electrophile is named halogen bond (XB). In this chapter, it is discussed how the practice and the concept of XB developed and a brief history of the interaction is presented. Papers (either from the primary or secondary literature) which have reported major experimental findings in the field or which have given important theoretical contributions for the development of the concept are recollected in order to trace how a unifying and comprehensive categorization emerged encompassing all interactions wherein halogen atoms function as the electrophilic site.


Crystal engineering Halogen bond Noncovalent interactions Self-assembly Supramolecular chemistry 



We are grateful to all colleagues, graduate and Ph.D. students, and postdoctoral associates who worked with us on XB. Some of them are mentioned in the references. Their dedication and enthusiasm has been fundamental. The authors are also grateful to the IUPAC for supporting the project no. 2009-032-1-100 “Categorizing Halogen Bonding and Other Noncovalent Interactions Involving Halogen Atoms.”


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Copyright information

© Springer International Publishing Switzerland 2014

Authors and Affiliations

  • Gabriella Cavallo
    • 1
    Email author
  • Pierangelo Metrangolo
    • 1
  • Tullio Pilati
    • 1
  • Giuseppe Resnati
    • 1
  • Giancarlo Terraneo
    • 1
  1. 1.Laboratory of Nanostructured Fluorinated Materials (NFMLab), Department of Chemistry, Materials, and Chemical Engineering “Giulio Natta”Politecnico di MilanoMilanoItaly

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