Experimental measurement of noncovalent interactions between halogens and aromatic rings

Harry Adams, Scott L. Cockroft, Claudio Guardigli, Christopher A. Hunter*, Kevin R. Lawson, Julie Perkins, Sharon E. Spey, Christopher J. Urch, Rhonan Ford

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Chemical double mutant cycles have been used to quantify the interactions of halogens with the faces of aromatic rings in chloroform. The halogens are forced over the face of an aromatic ring by an array of hydrogen-bonding Interactions that lock the complexes in a single, well-defined conformation. These interaction can also be engineered, into the crystal structures of simpler model compounds, but experiments in solution show that the halogen-aromatic interactions observed in the solid state are all unfavourable, regardless of whether the aromatic rings contain electron-withdrawing or electron-donating substituents. The halogen-aromatic Interactions are repulsive by 1-3kJmol -1. The interactions with fluorine are slightly less favourable than with chlorine and bromine.

Original languageEnglish
Pages (from-to)657-665
Number of pages9
JournalChemBioChem
Volume5
Issue number5
DOIs
Publication statusPublished - 3 May 2004

Keywords

  • Double mutant cycles
  • Halogens
  • Hydrogen bonds
  • Molecular recognition
  • Pi interactions

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