The Halogen Bond

The halogen bond 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. In this fairly extensive review, after a brief history of the interaction, we will provide the reader with a snapshot of where the research on the halogen bond is now, and, perhaps, where it is going. The specific advantages brought up by a design based on the use of the halogen bond will be demonstrated in quite different fields spanning from material sciences to biomolecular recognition and drug design.

• Publication year

  2016

• Venue

  Chemical Reviews

• Publication date

  2016-01-26

• Fields of study

  Medicine, Materials Science, Chemistry

• Identifiers
  DOI 10.1021/acs.chemrev.5b00484PMID 26812185PMCID 4768247
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Halogen Bonds in Organic Synthesis and Organocatalysis

  2016cited by this paper
• Halogen bonding in the design of organic phosphors.

  2016cited by this paper
• Solid-state NMR study of halogen-bonded adducts.

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• Correct electrostatic treatment of noncovalent interactions: the importance of polarization

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• A Halogen-Bonded Dimeric Resorcinarene Capsule.

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• Halogen bonds with coordinative nature: halogen bonding in a S–I+–S iodonium complex

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• Exploring σ-hole bonding in XH3Si···HMY (X=H, F, CN; M=Be, Mg; Y=H, F, CH3) complexes: a “tetrel-hydride” interaction

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• Halogen bonds in organic synthesis and organocatalysis.

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• Competition of C(sp²)-X···O halogen bonding and lone pair···π interactions: cryospectroscopic study of the complexes of C₂F₃X (X = F, Cl, Br, and I) and dimethyl ether.

  2015cited by this paper
• Strength of the pnicogen bond in complexes involving group Va elements N, P, and As.

  2015cited by this paper
• Halogen-Bond-Assisted Guest Inclusion in a Synthetic Cavity.

  2015cited by this paper
• Anion receptors based on halogen bonding with halo-1,2,3-triazoliums.

  2015cited by this paper
• Formation of Halogen Bond-Based 2D Supramolecular Assemblies by Electric Manipulation.

  2015cited by this paper
• Easily crosslinkable side-chain azobenzene polymers for fast and persistent fixation of surface relief gratings

  2015cited by this paper
• Halogen Bonding II: Impact on Materials Chemistry and Life Sciences

  2015cited by this paper
• Halogen bonding molecular capsules.

  2015cited by this paper
• Intramolecular Halogen Bonding in Solution: 15N, 13C, and 19F NMR Studies of Temperature and Solvent Effects

  2015cited by this paper
• A cryospectroscopic infrared and Raman study of the CX⋯π halogen bonding motif: complexes of the CF3Cl, CF3Br, and CF3I with ethyne, propyne and 2-butyne.

  2015cited by this paper
• Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface patterning

  2015cited by this paper
• Encapsulation of Halocarbons in a Tetrahedral Anion Cage.

  2015cited by this paper
• Tipping the Balance with the Aid of Stoichiometry: Room Temperature Phosphorescence versus Fluorescence in Organic Cocrystals

  2015cited by this paper
• Liquid Crystals for Bio-medical Applications

  2015cited by this paper
• Infrared and Raman measurements of halogen bonding in cryogenic solutions.

  2015cited by this paper
• Supramolecular amplification of amyloid self-assembly by iodination

  2015cited by this paper
• Mechanism and application of halogen bond induced fluorescence enhancement and iodine molecule cleavage in solution

  2015cited by this paper
• Halogen bonding in the gas phase: a comparison of the iodine bond in B⋯ICl and B⋯ICF3 for simple Lewis Bases B.

  2015cited by this paper
• Solution-phase self-assembly of complementary halogen bonding polymers.

  2015cited by this paper
• Fluorinated azobenzenes with highly strained geometries for halogen bond-driven self-assembly in the solid state

  2015cited by this paper
• Characteristics of a σ-Hole and the Nature of a Halogen Bond.

  2015cited by this paper
• Mathematical modeling and physical reality in noncovalent interactions

  2015cited by this paper
• N⋯I halogen bonding supported stabilization of a discrete pseudo-linear [I12]2− polyiodide

  2015cited by this paper
• Exploring Supramolecular Self-Assembly of Tetraarylporphyrins by Halogen Interactions. 3. Tin(L)2(A2B2-Porphyrin) Arrays Supported by Concerted Halogen and Hydrogen Bonding

  2015cited by this paper
• Tailoring magnetic properties of molecular materials through non-covalent interactions

  2015cited by this paper
• Application of polarizable ellipsoidal force field model to pnicogen bonds

  2015cited by this paper
• Halogen bonding enhances nonlinear optical response in poled supramolecular polymers

  2015cited by this paper
• Discriminating halogen-bonding from other noncovalent interactions by a combined NOE NMR/DFT approach.

  2015cited by this paper
• Halogen Bonding in Supramolecular Chemistry.

  2015cited by this paper
• Halogen bond: a long overlooked interaction.

  2015cited by this paper
• Characterisation of the Weak Halogen Bond in N 2 ···ICF 3 by Pure Rotational Spectroscopy

  2015cited by this paper
• Halogen-bonded photoresponsive materials.

  2015cited by this paper
• Pnicogen and hydrogen bonds: complexes between PH3X(+) and PH2X systems.

  2015cited by this paper
• Organizing radical species in the solid state with halogen bonding.

  2015cited by this paper
• Chalcogen-bonded complexes. Selenium-bound adducts of NH3, H2O, PH3, and H2S with OCSe, SCSe, and CSe2

  2015cited by this paper
• Statistical analysis of σ-holes: a novel complementary view on halogen bonding.

  2014cited by this paper
• Azobenzene-based difunctional halogen-bond donor: towards the engineering of photoresponsive co-crystals.

  2014cited by this paper
• The exploration of supramolecular interactions stemming from the [UO2(NCS)4(H2O)]2− tecton and substituted pyridinium cations

  2014cited by this paper
• Inter-layer charge disproportionation in the dual-layer organic metal (tTTF-I)2ClO4 with unsymmetrical I···O halogen bond interactions.

  2014cited by this paper
• Halogen- and Hydrogen-Bonded Salts and Co-crystals Formed from 4-Halo-2,3,5,6-tetrafluorophenol and Cyclic Secondary and Tertiary Amines: Orthogonal and Non-orthogonal Halogen and Hydrogen Bonding, and Synthetic Analogues of Halogen-Bonded Biological Systems

  2014cited by this paper
• Experimental evidence for 'carbon bonding' in the solid state from charge density analysis.

  2014cited by this paper
• Three mixed-ligand coordination networks modulated by flexible N-donor ligands: syntheses, topological structures, and temperature-sensitive luminescence properties

  2014cited by this paper
• The strength and directionality of a halogen bond are co-determined by the magnitude and size of the σ-hole.

  2014cited by this paper
• Concentration dependent halogen-bond density in the 2D self-assembly of a thienophenanthrene derivative at the aliphatic acid/graphite interface.

  2014cited by this paper
• Competition and cooperation: hydrogen and halogen bonding in co-crystals involving 4-iodotetrafluorobenzoic acid, 4-iodotetrafluorophenol and 4-bromotetrafluorophenol

  2014cited by this paper
• Halogen bonded analogues of deep cavity cavitands.

  2014cited by this paper
• Tailoring intermolecular interactions for efficient room-temperature phosphorescence from purely organic materials in amorphous polymer matrices.

  2014cited by this paper
• Fluorine-induced J-aggregation enhances emissive properties of a new NLO push–pull chromophore

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• Synthesis of an extended halogen-bonded metal–organic structure in a one-pot mechanochemical reaction that combines covalent bonding, coordination chemistry and supramolecular synthesis

  2014cited by this paper
• Halogen Bond: Its Role beyond Drug-Target Binding Affinity for Drug Discovery and Development

  2014cited by this paper
• Humidity-responsive liquid crystalline polymer actuators with an asymmetry in the molecular trigger that bend, fold, and curl.

  2014cited by this paper
• Tuning the halogen/hydrogen bond competition: a spectroscopic and conceptual DFT study of some model complexes involving CHF2I.

  2014cited by this paper
• Iodide-induced shuttling of a halogen- and hydrogen-bonding two-station rotaxane.

  2014cited by this paper
• New strategies and implications for the photoalignment of liquid crystalline polymers

  2014cited by this paper
• The phosphorescent co-crystals of 1,4-diiodotetrafluorobenzene and bent 3-ring-N-heterocyclic hydrocarbons by C–I⋯N and C–I⋯π halogen bonds

  2014cited by this paper
• Interaction of the electrophilic bis(pentafluorophenyl)iodonium cation [(C6F5)2I]+ with the ambident pseudohalogenide anions [SCN]− and [CN]−

  2014cited by this paper
• The many faces of halogen bonding: a review of theoretical models and methods

  2014cited by this paper
• The structural landscape of heteroaryl-2-imidazoles: competing halogen- and hydrogen-bond interactions

  2014cited by this paper
• The phosphorescent behaviors of 9-bromo- and 9-iodophenanthrene in crystals modulated by π–π interactions, C–H⋯π hydrogen bond and C–I⋯π halogen bond

  2014cited by this paper
• Observation of strong halogen bonds in the solid state structures of bis-haloimidazolium macrocycles

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• ortho-Fluoroazobenzenes: visible light switches with very long-Lived Z isomers.

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• Halotriazolium axle functionalised [2]rotaxanes for anion recognition: investigating the effects of halogen-bond donor and preorganisation.

  2014cited by this paper
• Halogen bonding in water results in enhanced anion recognition in acyclic and rotaxane hosts.

  2014cited by this paper
• Effect of N-methyl and ethyl on phosphorescence of carbazole in cocrystals assembled by CI⋯π halogen bond, π-hole⋯π bond and other interactions using 1,4-diiodotetrafluorobenzene as donor

  2014cited by this paper
• The halogen bond in thiirane···ClF: an example of a Mulliken inner complex.

  2014cited by this paper
• Probing halogen bonds with solid-state NMR spectroscopy: observation and interpretation of J(77Se,31P) coupling in halogen-bonded PSe⋯I motifs

  2014cited by this paper
• An all-halogen bonding rotaxane for selective sensing of halides in aqueous media.

  2014cited by this paper
• Tetragonal porous networks made by rod-like molecules on Au(1 1 1) with halogen bonds

  2014cited by this paper
• Directed synthesis of a halogen-bonded open porphyrin network

  2014cited by this paper
• A solvent-resistant halogen bond

  2014cited by this paper
• Halogen bonds in crystal TTF derivatives: an ab initio quantum mechanical study.

  2014cited by this paper
• Halogen bonds in crystal engineering: like hydrogen bonds yet different.

  2014cited by this paper
• Polymorphs and co-crystals of haloprogin: an antifungal agent

  2014cited by this paper
• Halogen bonding of (iodoethynyl)benzene derivatives in solution.

  2014cited by this paper
• Factors affecting the strengths of σ-hole electrostatic potentials

  2014cited by this paper
• σ-Hole bonding: a physical interpretation.

  2014cited by this paper
• On-surface solvent-free crystal-to-co-crystal conversion by non-covalent interactions.

  2014cited by this paper
• Electrical magnetochiral anisotropy in a bulk chiral molecular conductor

  2014cited by this paper
• Lithium cation conducting TDI anion-based ionic liquids.

  2014cited by this paper
• A reduced radial potential energy function for the halogen bond and the hydrogen bond in complexes B···XY and B···HX, where X and Y are halogen atoms.

  2014cited by this paper
• Halogen bond-assisted electron transfer reactions of aliphatic bromosubstituted electrophiles.

  2014cited by this paper
• Synthesis and catalytic alcohol oxidation and ketone transfer hydrogenation activity of donor-functionalized mesoionic triazolylidene ruthenium(II) complexes.

  2014cited by this paper
• Pseudilins: halogenated, allosteric inhibitors of the non-mevalonate pathway enzyme IspD.

  2014cited by this paper
• On The Nature of the Halogen Bond.

  2014cited by this paper
• Synergistic spin transition between spin crossover and spin-Peierls-like singlet formation in the halogen-bonded molecular hybrid system: [Fe(Iqsal)2 ][Ni(dmit)2 ]⋅CH3 CN⋅H2 O.

  2014cited by this paper
• Photo-mechanical azobenzene cocrystals and in situ X-ray diffraction monitoring of their optically-induced crystal-to-crystal isomerisation

  2014cited by this paper
• Halogen- and hydrogen-bonding catenanes for halide-anion recognition.

  2014cited by this paper
• Halogen bonding of electrophilic bromocarbons with pseudohalide anions.

  2014cited by this paper
• σ-Hole Interactions of Covalently-Bonded Nitrogen, Phosphorus and Arsenic: A Survey of Crystal Structures

  2014cited by this paper
• Organic photomechanical materials.

  2014cited by this paper
• Halogen bond and free internal rotation: the microwave spectrum of CF3Cl-dimethyl ether.

  2014cited by this paper
• Open bis(triazolium) structural motifs as a benchmark to study combined hydrogen- and halogen-bonding interactions in oxoanion recognition processes.

  2014cited by this paper

• Edge Reconstruction Drives Electronic and Catalytic Functions in Bilayer Iodinene

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• Organocatalytic Acetalization of Aldehydes Utilizing N‐Heterocyclic Iod(az)olium Salts as the Halogen‐Bonding Catalysts

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• Self-Healing Beyond Molecular Iodine Locking in Formamidinium Lead Triiodide Perovskites

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• Structural Aspects of Proline Methanologues in Drug Design, Optimization, and Development.

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• Ultrahigh fluorescence efficiency via halogen-based bonding regulation in regioisomeric chloro-tetraphenylethylene derivatives

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• Halogen Bonds under Electric Field with Quantum Accuracy and Relativistic Basis Sets

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• Halogen-Bond Coupled Halogenated-π-Conjugation Enables Giant Birefringence in Hydrogen-Bonded Organic Frameworks.

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• Hydrogen and Halogen Bond Interactions with 2,6-Dimethoxypyridine.

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• Impact of halogen-bonding interactions on M–X bond activation pathways: a perspective

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• High-voltage Zn–Br/Cl battery via three-electron transfer leveraging a water-in-salt electrolyte

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• Halogen Bonding vs. π-Stacked (Charge-Transfer) Interaction of Phenothiazine

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• Fundamentals and solid-state applications of π-hole-driven molecular recognition

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• Structural diversity of supramolecular networks composed of 2,1,3-chalcogenadiazole silver( i ) complexes: the role of chalcogen bonding in molecular self–assembly

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• Nascent stereocontrolling approaches in σ-hole based catalysis

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• DIH-Catalyzed Vinylsulfonation via Halogen Bonding Activation of Sulfonyl Iodides for Late-Stage Functionalization.

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• Chemical and ecological evaluation of rhodanine derivatives through aquatic bioindicators

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• Spectrochemical, medicinal, and toxicological studies of Metronidazole and its derivatives: a quantum chemical and drug-design approach

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• Parallels between the chloro and methoxy groups for potency optimization.

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• Solid-state NMR characterization of weak interactions in molecular crystals

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• Asymmetric Bio- and Organocatalysis: Historical Aspects and Concepts

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• Dual σ- and π-Hole Chalcogen Bonding with Cooperative π-Stacking: Noncovalent Forces That Amplify Halogen Bond Donors

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• Photoexcited Phosphine–Acyl Iodide Complexes for the Generation of Acyl Radicals

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• Halogen bonding interactions in epoxyisoxazolo[5,4-e]isoindol derivatives: X-ray structures and theoretical study

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• The rise of halogen bonding in (stereo)selective supramolecular catalysis

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• Unveiling σ-stacking in Pentane Dimers using Matrix Isolation Infrared Spectroscopy and Ab initio Computations: The Hidden Architecture of Weak Alkane Interactions

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• Dichlorine-Containing Chlorothallate(III) (Me4N)3{[Tl2Cl9](Cl2)}: Crystal Structure and Thermal Stability.

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• The acid-base concept in modern supramolecular chemistry

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• Non-covalent interactions in the structure and function of metalloenzymes and related systems

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• Non-canonical σ-hole interactions: halogen, chalcogen, and pnictogen bonds in biomolecular structure and drug design

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• Halide Bond Assisted Double Desymmetrization of Meso‐Dicarboxylic Acids with Symmetrical Olefins via Asymmetric Halogenation

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• Redox-Switchable Halogen Bonding in Haloanthracene Mediators Enables Efficient Electrocatalytic C-N Coupling.

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• The use of an interpretable machine-learning approach to disclose the molecular assemblage on melting transition

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• [N⋯Br⋯N]+ Type Halogen Bonding: From Structure to Applications.

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• Constructing an Optimum Receptor Based on Trifurcated Chalcogen Bonding.

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• Perfluoroalkylation reactions via halogen-bonded electron donor-acceptor (EDA) complexes of amines and perfluoroalkyl halides under visible light

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• Revisiting the Nature of Frequencies Shifted to Red or Blue in the LiH⋯HX Complexes (X = F, Cl, CN , and CCH ) and the Role of the Dihydrogen Bond Strength

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• Impact of Peripheral Halogenation on the Structure-Property Relationships of Tetrathienoanthracene (TTA) Derivatives: Synthesis, Structural Characterization, and Theoretical Studies

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• Shedding Light on the Capabilities of Heteroditopic Mechanically Interlocked Molecules in Ion-Pair Sensing.

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• Benefits of Categorizing Noncovalent Bonds Based on Hydrogen, Halogen, Chalcogen, and Pnictogen Bonds.

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• Controlling the Arrangement of [Fe4L6]8+ Cages in the Solid State.

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