Net attractive interaction involving one of the halogen elements
In chemistry, a halogen bond (XB) 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.[1] Like a hydrogen bond, the result is not a formal chemical bond, but rather a strong electrostatic attraction.[2][3] 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;[2][3][4] drug design and biochemistry;[5][6] crystal engineering[6] and liquid crystals;[2] and organic catalysis.[6]
^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.
^ abcMetrangolo 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.
^ abGilday 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.
^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.
^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.
^ abcCavallo 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.
chemistry, a halogenbond (XB) occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in...
as halogenoalkanes or alkyl halides) are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although...
The halogens (/ˈhælədʒən, ˈheɪ-, -loʊ-, -ˌdʒɛn/) are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine...
interactions, quadrupole interactions, π–π interactions, hydrogen bonding, halogenbonding, London dispersion forces, and in some molecular solids, coulombic...
respect to their heavier analogues. In some cases a similar halogenbond can be formed by a halogen atom located between two electronegative atoms on different...
A halogen addition reaction is a simple organic reaction where a halogen molecule is added to the carbon–carbon double bond of an alkene functional group...
In chemistry, a chalcogen bond (ChB) is an attractive interaction in the family of σ-hole interactions, along with halogen bonds. Electrostatic, charge-transfer...
Haloalkanes are a class of molecule that is defined by a carbon–halogenbond. This bond can be relatively weak (in the case of an iodoalkane) or quite...
tetrel bonding (in which a sigma hole resides on an atom of group IV), pnictogen bonding (group V), chalcogen bonding (group VI), and halogenbonding (group...
states. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in...
examples are molecules with a nitrogen-halogenbond, azo compounds, and organic and inorganic peroxides. Halogens undergo homolytic fission relatively easily...
one-step mechanism in which carbon-hydrogen and carbon-halogen bonds break to form a double bond (C=C Pi bond). The specifics of the reaction are as follows:...
element; it has symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its...
shown to coordinate to Lewis acids through electrostatic, σ-hole (see halogenbond) interactions, between the Lewis basic oxygen atoms of the crown ether...
element; it has symbol I and atomic number 53. The heaviest of the stable halogens, it exists at standard conditions as a semi-lustrous, non-metallic solid...
halides cannot undergo the classic 'backside' SN2 reaction. The carbon-halogenbond is in the plane of the ring because the carbon atom has a trigonal planar...
a reduced bond order, all three halogen atoms are tightly bound. The fluorine–fluorine bond of trifluoride, with bond order 0.5, has a bond-strength is...
reactions of the halogens). Chemical compounds with double bonds Ethylene Carbon-carbon double bond Acetone Carbon-oxygen double bond Dimethyl sulfoxide...
also has an interest in crystal engineering, in particular by using the halogenbond. He is Vice-President and President-Elect of the Physical and Biophysical...
low boiling points (−72 °C and −6 °C respectively) and short nitrogen–halogenbond lengths (N–F 135 pm, N–Cl 184 pm). Addition of one electron forms the...
strength of the bond between the carbon and halogen atom. The bond dissociation energies of carbon-halogen bonds are described as: H3C−I (234 kJ/mol),...
afforded by the radial-nodeless 3d orbitals. Like the other carbon–halogen bonds, the C–Br bond is a common functional group that forms part of core organic...
is offset by the larger bond enthalpy of the newly introduced C-O bond (when compared to that of the cleaved C-halogenbond). Formation of epoxides from...
carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Carbon–halogenbond strengths, or bond dissociation energies are...
haloalkanes. If the two carbon atoms at the double bond are linked to a different number of hydrogen atoms, the halogen is found preferentially at the carbon with...
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