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Halogen bonding with the halogenabenzene bird structure, halobenzene and halocyclopentadiene

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Abstract

The ability of the “bird-like” halogenabenzene molecule, referred to as X-bird (X= Cl to At), to form halogen-bonded complexes with the nucleophiles H2O and NH3 was investigated using double-hybrid density functional theory and the aug-cc-pVTZ/aug-cc-pVTZ-PP basis set. The structures and interaction energies were compared with 5-halocyclopenta-1,3-diene (halocyclopentadiene; an isomer of halogenabenzene) and halobenzene, also complexed with H2O and NH3. The unusual structure of the X-bird, with the halogen bonded to two carbon atoms, results in two distinct σ-holes, roughly at the extension of the C-X bonds. Based on the behaviour of the interaction energy (which increases for heavier halogens) and van der Waals (vdW) ratio (which decreases for heavier halogens), it is concluded that the X-bird forms proper halogen bonds with H2O and NH3. The interaction energies are larger than those of the halogen-bonded complexes involving halobenzene and halocyclopentadiene, presumably due to the presence of a secondary interaction.
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Original languageEnglish
Pages (from-to)2111-2118
JournalJournal of Computational Chemistry
Volume40
Issue number24
Early online date29 May 2019
DOIs
Publication statusPublished - 15 Sep 2019

    Research areas

  • Halogen bond, Halogenabenzene, Halobenzene, Halocyclopentadiene, Double hybrid density functional theory

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