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Net attractive interaction involving one of the halogen elements
a halogen bond (XB or HaB) occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom
Halogen_bond
Group of chemical compounds derived from alkanes containing one or more halogens
as halogenoalkanes or alkyl halides) are alkanes containing one or more halogen substituents of hydrogen . They are a subset of the general class of halocarbons
Haloalkane
Group of chemical elements
like the triiodide ion. Look up halogen in Wiktionary, the free dictionary. Halogen bond Halogen addition reaction Halogen lamp Halogenation Interhalogen
Halogen
Italian chemist
also has an interest in crystal engineering, in particular by using the halogen bond. He is past-president of the Physical and Biophysical Chemistry Division
Pierangelo_Metrangolo
Chemical bond which does not involve the sharing of electrons
similar to the dipole–dipole interaction known as hydrogen bonding. In halogen bonding, a halogen atom acts as an electrophile, or electron-seeking species
Non-covalent_interaction
Net attractive interaction involving one of the chalcogen elements
In chemistry, a chalcogen bond (ChB) is an attractive interaction in the family of σ-hole interactions, along with halogen bonds. Electrostatic, charge-transfer
Chalcogen_bond
Association of atoms to form chemical compounds
respect to their heavier analogues. In some cases a similar halogen bond can be formed by a halogen atom located between two electronegative atoms on different
Chemical_bond
Solid consisting of discrete molecules
interactions, quadrupole interactions, π–π interactions, hydrogen bonding, halogen bonding, London dispersion forces, and in some molecular solids, coulombic
Molecular_solid
Intermolecular forces between oppositely-charged sites on molecules
tetrel bonding (in which a sigma hole resides on an atom of group IV), pnictogen bonding (group V), chalcogen bonding (group VI), and halogen bonding (group
Sigma_hole_interactions
Italian chemist
al. Halogen Bonding in Supramolecular Chemistry Angew. Chem. Int. Ed. 2008, 47, 6114-6127 ( DOI: 10.1002/anie.200800128 ) G. Resnati et al. Halogen bonded
Giuseppe_Resnati
Covalent bond between carbon and fluorine atoms
can have a bond dissociation energy (BDE) of up to 130 kcal/mol. The BDE (strength of the bond) of C–F is higher than other carbon–halogen and carbon–hydrogen
Carbon–fluorine_bond
Molecules that can produce radicals and catalyze radical reactions
examples are molecules with a nitrogen-halogen bond, azo compounds, and organic and inorganic peroxides. Halogens undergo homolytic fission relatively easily
Radical_initiator
Reaction which adds a halogen molecule
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
Halogen_addition_reaction
Chemical bonding involving attraction between ions
electronegative atoms (such as halogens) often have only one or two empty electron states in their valence shell, and frequently bond with other atoms or gain
Ionic_bonding
Ring molecules with several ether (–O–) groups
shown to coordinate to Lewis acids through electrostatic, σ-hole (see halogen bond) interactions, between the Lewis basic oxygen atoms of the crown ether
Crown_ether
Chemical reaction
stereochemistry of the double bond. The presence of alkoxyl or related chelating groups accelerates lithium–halogen exchange. Lithium halogen exchange is typically
Metal–halogen_exchange
Chemical compound
strong halogen bond donor. Perkins, Catherine; Libri, Stefano; Adams, Harry; Brammer, Lee (2012). "Diiodoacetylene: Compact, Strong Ditopic Halogen Bond Donor"
Diiodoacetylene
Group of atoms giving a molecule characteristic properties
Haloalkanes are a class of molecule that is defined by a carbon–halogen bond. This bond can be relatively weak (in the case of an iodoalkane) or quite
Functional_group
Covalent bond involving 12 bonding electrons
A sextuple bond is a type of covalent bond involving 12 bonding electrons and in which the bond order is 6. The only known molecules with true sextuple
Sextuple_bond
Chemical element with atomic number 35 (Br)
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
Bromine
Chemical bond involving four bonding electrons; has one sigma plus one pi bond
reactions of the halogens). Chemical compounds with double bonds Ethylene carbon–carbon double bond Acetone carbon–oxygen double bond Dimethyl sulfoxide
Double_bond
Study of compounds with carbon to zinc bonds
initial step is an oxidative addition of zinc metal into the carbon-halogen bond, thus forming a carbon-zinc enolate. This C-Zn enolate can then rearrange
Organozinc_chemistry
Branch of organic chemistry
metal into the carbon-halogen bond. However, such reactions are temperamental, typically requiring a very weak carbon-halogen bond (e.g. an alkyl iodide
Organotin_chemistry
Chemical element with atomic number 53 (I)
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
Iodine
Chemical reaction in which a carbon-halogen bond is cleaved
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),
Dehalogenation
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
Polyhalogen_ions
Designing solid structures with tailored properties
engineering strategies currently in use are hydrogen- and halogen bonding and coordination bonding. These may be understood with key concepts such as the
Crystal_engineering
Chemical reaction mechanism
halides cannot undergo the classic 'backside' SN2 reaction. The carbon-halogen bond is in the plane of the ring because the carbon atom has a trigonal planar
Nucleophilic aromatic substitution
Nucleophilic_aromatic_substitution
the carbon-halogen bond. At local contact temperatures ranging between 305-330 °C, the additive thermally decomposes and the reactive halogen atoms form
Extreme_pressure_additive
Polyatomic ion
low boiling points (−72 °C and −6 °C respectively) and short nitrogen–halogen bond lengths (N–F 135 pm, N–Cl 184 pm). Addition of one electron forms the
Nitronium_ion
Category of chemical elements
AV & Matile S 2015, "Anion transport with halogen bonds", in Metrangolo P & Resnati G (eds.), Halogen Bonding I: Impact on Materials Chemistry and Life
Nonmetal
Organic compound containing at least one covalent carbon-bromine bond
carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Carbon–halogen bond strengths, or bond dissociation energies are
Organobromine_chemistry
Chemical compounds containing iodine
Iodine is quite reactive, but it is much less reactive than the other halogens. For example, while chlorine gas will halogenate carbon monoxide, nitric
Iodine_compounds
Chemical compound
cis-polydichloroacetylene. Like other haloalkynes, dichloroacetylene is a strong halogen bond donor. It forms an air-stable azeotrope with ether, boiling at 32 °C
Dichloroacetylene
Chemical compound
and [CuI2(CNXyl)4] (109 mg/mL). The effect is attributed to strong halogen bonding between the iodine atoms of the solvent and the halide ligands of some
Diiodomethane
Chemical element with atomic number 17 (Cl)
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
Chlorine
Chemical compound
Müller-Bunz, Helge; Gilheany, Declan (2013). "Direct evidence of a multicentre halogen bond: Unexpected contraction of the P–XXX–P fragment in triphenylphosphine
Triphenylphosphine_dibromide
Three linked but pairwise separated rings
has been synthesized by design by Giuseppe Resnati and coworkers via halogen bond driven self-assembly. In order to access the molecular Borromean ring
Borromean_rings
Anions composed of many iodine atoms
Triiodide Polyhalogen ions Iodine–starch test Dye-sensitized solar cell Halogen bond Catenation Inorganic polymer Housecroft, Catherine E.; Sharpe, Alan G
Polyiodide
Electron in the outer shell of an atom's energy levels
(a covalent bond), or it can remove electrons from another atom (an ionic bond). The most reactive kind of nonmetal element is a halogen (e.g., fluorine
Valence_electron
Type of organic chemical reaction
involve loss of sigma bonded groups to form a pi bond on the structure, such as loss of hydrogen and halogen atoms from an alkane to form an alkene. The E2
Elimination_reaction
Organic compound containing at least one covalent carbon-iodine bond
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
Organoiodine_chemistry
Organic compounds with a carbon-carbon-oxygen ring
is offset by the larger bond enthalpy of the newly introduced C-O bond (when compared to that of the cleaved C-halogen bond). Formation of epoxides from
Epoxide
Use of metal-based Lewis acids to catalyze organic reactions
simple metal halide salt – promotes heterolytic cleavage of a carbon–halogen bond in an alkyl halide and generates a carbocation, which undergoes electrophilic
Lewis_acid_catalysis
Electrophilic addition of hydrogen halides to alkenes
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
Hydrohalogenation
Rule in geometry of individual molecules
2019-08-15. Retrieved 2023-12-06. Grabowski, Sławomir J. (2011-11-10). "Halogen Bond and Its Counterparts: Bent's Rule Explains the Formation of Nonbonding
Bent's_rule
Polymeric arrays of repeating units connected by non-covalent bonds
interactions, hydrogen bonding, Coulomb or ionic interactions, π-π stacking, metal coordination, halogen bonding, chalcogen bonding, and host–guest interaction
Supramolecular_polymer
Chemical compounds containing C–Li bonds
solution. Lithium–halogen exchange involves heteroatom exchange between an organohalide and organolithium species. Lithium–halogen exchange is very useful
Organolithium_reagent
Enzyme
carbon-halogen bond through the formation of an epoxide from a vicinal hydroxyl group. The substrate binds to the active site through hydrogen bonding that
Halohydrin_dehalogenase
Any chemical compound having at least one bromine atom
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
Bromine_compounds
Net attractive interaction involving one of the pnictogen elements
may be in the same or another molecule. Closely related to halogen and chalcogen bonding, pnictogen bonds are a form of non-covalent interaction which
Pnictogen_bond
Organic reaction
described as "organometallic". Zinc metal is inserted into the carbon-halogen bond of the α-haloester by oxidative addition 1. This compound dimerizes and
Reformatsky_reaction
Molecule containing main group elements with more than eight valence electrons
below. The Si-halogen bonds range from close to the expected van der Waals value in A (a weak bond) almost to the expected covalent single bond value in C
Hypervalent_molecule
Class of enzymes
2NO4, and PDB: 2NO5. Goldman P, Milne GW, Keister DB (1968). "Carbon-halogen bond cleavage. 3. Studies on bacterial halidohrolases". J. Biol. Chem. 243
(S)-2-haloacid_dehalogenase
Chemical compound
to the halogen bonding concept, the trichloride anion can be described as a donor-acceptor complex consisting of a chloride anion (the halogen donor)
Triethylmethylammonium trichloride
Triethylmethylammonium_trichloride
Group of atoms introduced into a compound to prevent subsequent reactions
1016/S0040-4039(00)97045-X. Corrado Malanga, Serena Mannucci, Luciano Lardicci: "Carbon-halogen bond activation by nickel catalyst: Synthesis of alkenes, from 1,2-dihalides"
Protecting_group
Organic derivative of iodine
partially-covalent bond between the iodine and the counterion. Some authors have described this interaction as an example of halogen bonding, but the interaction
Hypervalent organoiodine compounds
Hypervalent_organoiodine_compounds
Chemical reaction
N-halogenated ammonium salt 22 undergoes homolytic cleavage of the nitrogen-halogen bond to generate the nitrogen-centered radical cation 23. In contrast, it
Hofmann–Löffler_reaction
American physicist and chemist (1896–1986)
burial. Mulliken symbols Adiabatic electron transfer Bonding molecular orbital Delta bond Halogen bond Walsh diagram Platt, J. R. (1966). "1966 Nobel Laureate
Robert_S._Mulliken
Norwegian physical chemist and Nobel Laureate (1897–1981)
a Knight of the Order of St. Olav in 1960. Cyclohexane conformation Halogen bond Tor Dahl. "Odd Hassel". Norsk biografisk leksikon. Retrieved February
Odd_Hassel
Class of germanium (II) compounds
caged singlet radical pair was proposed for C-Cl bond insertion. However, the interaction between halogen electrons and empty p-orbital of the germylene
Germylene
Permanent bond dipole due to electron-rich or -poor groups in a molecule
permanent dipole in a bond. It is present in a σ (sigma) bond, unlike the electromeric effect which is present in a π (pi) bond. The halogen atoms in an alkyl
Inductive_effect
Term which determines total number of rings and π bonds
the compound c = number of nitrogen atoms in the compound f = number of halogen atoms in the compound or r i n g s + π b o n d s = C − H 2 − X 2 + N
Degree_of_unsaturation
Organic cation
effects. The linear sp-hybridized vinyl cation may be attacked by the halogen from two directions. When attacked from the less sterically hindered side
Vinyl_cation
Chemical phenomenon
carbon-hydrogen and carbon-halogen bonds break to form a double bond. C=C Pi bond. An E1 reaction is the Ionization of the carbon-halogen bond breaking to give
Evelyn_effect
Molecule containing only halogen elements of two or more kinds
those of the two parent halogens. The covalent bond between the two atoms has some ionic character, the less electronegative halogen, X, being oxidised and
Interhalogen
Any chemical compound having at least one fluorine atom
carbon–fluorine bond of the smaller molecules is formed in three principal ways: Fluorine replaces a halogen or hydrogen, or adds across a multiple bond. The direct
Fluorine_compounds
Cross-coupling reaction between boronic acid & an organohalide
oxidative addition step breaks the carbon-halogen bond where the palladium is now bound to both the halogen (X) as well as the R1 group. Oxidative addition
Suzuki_reaction
Any onium ion containing a halogen atom carrying a positive charge
from the formal addition of a halogenium ion X+ to a C=C double bond, as when a halogen is added to an alkene. The formation of 5-membered halonium ions
Halonium_ion
Organic compounds that contain sulfur
represented as having a formal triple bond. A wide range of organosulfur compounds are known which contain one or more halogen atom ("X" in the chemical formulas
Organosulfur_chemistry
Indian chemist and professor (born 1970)
Bhatnagar Prize, one of the highest Indian science awards, in 2015. Halogen bond India portal Chemistry portal "Brief Profile of the Awardee". Shanti
Pradyut_Ghosh
Chemical compound
NIST. Retrieved 2 September 2025. Huber, Stefan (19 April 2021). Halogen Bonding in Solution. John Wiley & Sons. p. 157. ISBN 978-3-527-34731-5. Retrieved
Difluoroiodomethane
German chemist
Dietzek, M. Schmitt, J. Popp, M. D. Hager*, U. S. Schubert*: Polymeric halogen bond based donor systems showing self-healing behavior in thin films. In:
Ulrich_S._Schubert
Classification of membrane proteins including ion channels
Tris-thiourea Tripodal-based Chloride Carrier (TTT-CC) Family 2.B.16 The Halogen-bond-containing Compound Anion Carrier (HCAC) Family 2.B.17 The Isophthalaminde
Transporter Classification Database
Transporter_Classification_Database
Parameter used to characterize molecular geometry
Chojnacki, J. (2018). "Novel complexes possessing Hg‒(Cl, Br, I)···O=C halogen bonding and unusual Hg2S2(Br/I)4 kernel. The usefulness of τ4′ structural parameter"
Geometry_index
Hydrocarbon compound containing one or more C=C bonds
hydrocarbon containing one or more carbon–carbon double bonds. The double bond may be internal or at the terminal position. Terminal alkenes are also known
Alkene
Hydrocarbon compound containing one or more C≡C bonds
the H–C≡C bond angles are 180°. By virtue of this bond angle, alkynes are rod-like. Correspondingly, cyclic alkynes are rare due to bond strain. As such
Alkyne
Bonding of atoms of the same element into chains or rings
boron, silicon, phosphorus, sulfur and halogens. The ability of an element to catenate is primarily based on the bond energy of the element to itself, which
Catenation
Branch of chemistry
complexes may then be accessed from displacement of the newly formed bismuth-halogen bond with an alkyl or aryl lithium or Grignard reagent. For example: Me3Bi
Organobismuth_chemistry
Academic journal
Metrangolo, P.; Pilati, T; Resnati, G. (2006). "Halogen bonding and other noncovalent interactions involving halogens: a terminology issue". CrystEngComm. 8 (12):
CrystEngComm
Molecules of the form >N–S(=O)–
Maguire, A. R.; Lawrence, S. E. (2013). "Co-crystallisation Through Halogen Bonding with Racemic or Enantiopure Sulfinamides". CrystEngComm. 15 (37): 7571–7575
Sulfinamide
Chemical reaction
reaction. Typical electrophilic additions to alkenes with reagents are: Halogen addition reactions: X2 Hydrohalogenations: HX Hydration reactions: H2O
Electrophilic_addition
Russian chemist
mono- and dihalocarbenes (in particular, dichlorocarbene) across mercury-halogen bond, obtaining asymmetric mercury derivatives that contained a trichloromethyl
Oleg_Reutov
Chemical compound containing carbon and at least one halogen
one or more carbon atoms are linked by covalent bonds with one or more halogen atoms (fluorine, chlorine, bromine, iodine, or astatine – group 17) resulting
Halocarbon
Representation method in chemistry
The skeletal formula, line-angle formula, bond-line formula or shorthand formula of an organic compound is a type of minimalist structural formula representing
Skeletal_formula
Chemical notation
yield normal covalent bonds. A few examples of this type of ligand are H, halogens (Cl, Br, F, etc.), OH, CN, CH3, and NO (bent). L-type ligands are neutral
Covalent bond classification method
Covalent_bond_classification_method
Chemical compounds containing an –O–N≡C group
pseudohalic ion because its charge and reactivity are similar to those of the halogens. The name is derived from the Latin fulminātus, meaning to explode like
Fulminate
Atom, molecule, or ion that has an unpaired valence electron; typically highly reactive
K. (1956-04-01). "The Degradation Of Carboxylic Acid Salts By Means Of Halogen - The Hunsdiecker Reaction". Chemical Reviews. 56 (2): 219–269. doi:10
Radical_(chemistry)
Chemical compound
chlorides and fluorides: C4H9Li + RX → C4H9X + RLi (X = Br, I) This lithium–halogen exchange reaction is useful for preparation of several types of RLi compounds
N-Butyllithium
Diagrams for the bonding between atoms of a molecule and lone pairs of electrons
or Lewis electron dot structures (LEDs) – are diagrams that show the bonding between atoms of a molecule, as well as the lone pairs of electrons that
Lewis_structure
Chemical compound found in some lichens
of chlorine substituents in lichexanthones properties: the ionic and halogen bond interactions". Theoretical Chemistry Accounts. 137 (8). doi:10.1007/s00214-018-2294-0
Lichexanthone
Ming-Chang; Li, Jia-Jia; Lian, Jia-Min; Chen, Jin; Du, Ke-Zhao (March 2026). "Halogen-Bond Coupled Halogenated-π-Conjugation Enables Giant Birefringence in Hydrogen-Bonded
Giant_birefringence
American chemist
(2016-11-02). "Elucidating the Effects of Fluoro and Nitro Substituents on Halogen Bond Driven Assemblies of Pyridyl-Capped π-Conjugated Molecules". Crystal
Davita_Watkins
Chemical compound
5-HT6 receptor antagonist with procognitive activity - Importance of a halogen bond interaction to stabilize the binding". Scientific Reports. 7 (1) 41293
JNJ-18038683
Organometallic compounds used in organic synthesis
creating new carbon–carbon bonds. The carbon-magnesium bond in Grignard reagent is a polar covalent bond. The carbon atom has negative excess charge and acts
Grignard_reagent
System for naming organic chemical compounds
triple bond: ethyne (acetylene), propyne (methylacetylene). In haloalkanes and haloarenes (R−X), Halogen functional groups are prefixed with the bonding position
IUPAC nomenclature of organic chemistry
IUPAC_nomenclature_of_organic_chemistry
Yaxin Wang, Junhua Wang, Guo-Xing Li, Gang He, Gong Chen (2017-03-17), "Halogen-Bond-Promoted Photoactivation of Perfluoroalkyl Iodides: A Photochemical Protocol
Perfluoroalkyl_iodide
Award in crystallography
supramolecular synthon concept, and for establishing the structural significance of weak hydrogen bonding and halogen bonding in molecular crystals and biology.".
Ewald_Prize
Chemical compound
colorless liquid with a pleasant odor. Because it contains bromine, a halogen, it is part of a larger class of compounds known as alkyl halides. Because
2-Bromobutane
Functional group with the chemical structure R–S–S–R′
remove TCEP before modification of protein thiols. In Zincke cleavage, halogens oxidize disulfides to a sulfenyl halide: ArSSAr + Cl2 → 2 ArSCl More unusually
Disulfide
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