Halogen bond

In chemistry, a halogen bond (XB or HaB[1]) occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity.[2] Like a hydrogen bond, the result is not a formal chemical bond, but rather a strong electrostatic attraction.[3][4] Mathematically, the interaction can be decomposed in two terms: one describing an electrostatic, orbital-mixing charge-transfer and another describing electron-cloud dispersion. Halogen bonds find application in supramolecular chemistry;[3][4][5] drug design and biochemistry;[6][7] crystal engineering[7] and liquid crystals;[3] and organic catalysis.[7]

  1. ^ Varadwaj, Pradeep R.; Varadwaj, Arpita; Marques, Helder M.; Yamashita, Koichi (2024-07-03). "Definition of the Halogen Bond (IUPAC Recommendations 2013): A Revisit". Crystal Growth & Design. 24 (13): 5494–5525. doi:10.1021/acs.cgd.4c00228. ISSN 1528-7483.
  2. ^ Desiraju GR, Ho PS, Kloo L, Legon AC, Marquardt R, Metrangolo P, et al. (2013). "Definition of the Halogen Bond (IUPAC Recommendations 2013)". Pure Appl. Chem. 85 (8): 1711–1713. doi:10.1351/pac-rec-12-05-10.
  3. ^ a b c Metrangolo P, Neukirch H, Pilati T, Resnati G (May 2005). "Halogen bonding based recognition processes: a world parallel to hydrogen bonding". Accounts of Chemical Research. 38 (5): 386–395. doi:10.1021/ar0400995. PMID 15895976.
  4. ^ a b Gilday LC, Robinson SW, Barendt TA, Langton MJ, Mullaney BR, Beer PD (August 2015). "Halogen Bonding in Supramolecular Chemistry". Chemical Reviews. 115 (15): 7118–7195. doi:10.1021/cr500674c. PMID 26165273.
  5. ^ Metrangolo P, Resnati G (June 2001). "Halogen bonding: a paradigm in supramolecular chemistry". Chemistry. 7 (12): 2511–2519. doi:10.1002/1521-3765(20010618)7:12<2511::AID-CHEM25110>3.0.CO;2-T. PMID 11465442.
  6. ^ Auffinger P, Hays FA, Westhof E, Ho PS (November 2004). "Halogen bonds in biological molecules". Proceedings of the National Academy of Sciences of the United States of America. 101 (48): 16789–16794. Bibcode:2004PNAS..10116789A. doi:10.1073/pnas.0407607101. PMC 529416. PMID 15557000.
  7. ^ a b c Cavallo G, Metrangolo P, Milani R, Pilati T, Priimagi A, Resnati G, Terraneo G (February 2016). "The Halogen Bond". Chemical Reviews. 116 (4): 2478–2601. doi:10.1021/acs.chemrev.5b00484. PMC 4768247. PMID 26812185.