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Halogen Bonding in Hypervalent Iodine Compounds.

Luca Catalano1, Gabriella Cavallo1, Pierangelo Metrangolo2

  • 1Laboratory of Nanostructured Fluorinated Materials (NFMLab), Department of Chemistry, Materials, and Chemical Engineering "Giulio Natta", Politecnico di Milano, Via L. Mancinelli 7, 20131, Milan, Italy.

Topics in Current Chemistry
|January 27, 2016
PubMed
Summary
This summary is machine-generated.

Halogen bonds involve electrophilic halogens interacting with electron donors. This study proposes extending the halogen bond definition to longer, weaker interactions in hypervalent iodine compounds, offering a more descriptive term than secondary bonding.

Keywords:
Crystal engineeringHalogen bondHypervalent iodineSupramolecular chemistry

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Area of Science:

  • Inorganic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • Halogen bonds are typically defined for monovalent halogen derivatives, involving electrophilic halogens acting as Lewis acids.
  • Hypervalent iodine compounds feature complex bonding patterns around the iodine atom.
  • Understanding non-covalent interactions in these systems is crucial for predicting crystal structures and reactivity.

Purpose of the Study:

  • To demonstrate that geometric features in hypervalent iodine derivatives support classifying certain longer bonds as halogen bonds.
  • To propose the use of the term 'halogen bond' for specific interactions in hypervalent iodine compounds.
  • To highlight the descriptive advantages of 'halogen bond' over 'secondary bonding' for these interactions.

Main Methods:

  • Analysis of geometric features and bonding patterns in ionic and neutral hypervalent iodine derivatives (λ(3)- and λ(5)-iodanes).
  • Investigation of electron density distribution and electrostatic potential around iodine atoms.
  • Comparison of observed short contacts with established halogen bond definitions and geometrical prerequisites.

Main Results:

  • Anisotropic electron density distribution around iodine in hypervalent derivatives creates regions of positive electrostatic potential.
  • These positive potentials (caps) influence and potentially dictate crystal packing.
  • Short cation-anion contacts and interactions with lone-pair donors in iodane derivatives align with halogen bond characteristics.

Conclusions:

  • The directional nature and geometric prerequisites of interactions in hypervalent iodine compounds justify their classification as halogen bonds.
  • The term 'halogen bond' offers a more descriptive account of directionality and structure-interaction relationships compared to 'secondary bonding'.
  • This broadened definition enhances the understanding of intermolecular forces in hypervalent iodine chemistry and crystal engineering.