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Halogen bonding in differently charged complexes: basic profile, essential interaction terms and intrinsic σ-hole.

Zhengdan Zhu1, Guimin Wang1, Zhijian Xu1

  • 1CAS Key Laboratory of Receptor Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. zjxu@simm.ac.cn wlzhu@simm.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, China.

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This study reveals that halogen bonds (XB) are stable even with charged donors or acceptors. Orbital interactions and electron transfer explain these complex halogen bonding behaviors.

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Area of Science:

  • Supramolecular Chemistry
  • Computational Chemistry
  • Chemical Physics

Background:

  • Halogen bonds (XB) are crucial non-covalent interactions.
  • Understanding XB interactions with charged donors/acceptors is challenging.
  • Previous studies noted difficulties in explaining electrophilicity/nucleophilicity in charged XB systems.

Purpose of the Study:

  • To computationally explore 9 designed halogen bonding (XB) systems mimicking all possible charge states.
  • To elucidate the nature of halogen bonds involving differently charged donors and acceptors.
  • To understand the underlying mechanisms governing the stability and strength of these interactions.

Main Methods:

  • Computational design and exploration of 9 unique halogen bonding systems.
  • Calculation of binding energies for various halogen bond types (Cl, Br, I).
  • Analysis of orbital interactions, dispersion forces, and intermolecular electron transfer.

Main Results:

  • All designed halogen bonds (XB) were found to be stable, with significant binding energies.
  • Attractive orbital and dispersion interactions were consistently observed.
  • Unidirectional intermolecular electron transfer from acceptor to donor occurred in all complexes.
  • Intrinsic properties like the sigma-hole and acceptor electronics govern XB behavior regardless of charge.
  • Intramolecular charge redistribution enhances XB stability in a system-dependent manner.

Conclusions:

  • Orbital-based interactions successfully explain complex halogen bonding behaviors in charged systems.
  • Electrostatic interactions significantly influence overall halogen bond strength.
  • This research provides a framework for understanding and applying halogen bonds in diverse chemical contexts.