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interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Halogenov%C3%A1_vazba" title="Halogenová vazba – Czech" lang="cs" hreflang="cs" data-title="Halogenová vazba" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Halogenbindung" title="Halogenbindung – German" lang="de" hreflang="de" data-title="Halogenbindung" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Enlace_de_hal%C3%B3geno" title="Enlace de halógeno – Spanish" lang="es" hreflang="es" data-title="Enlace de halógeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Liaison_halog%C3%A8ne" title="Liaison halogène – French" lang="fr" hreflang="fr" data-title="Liaison halogène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%95%A0%EB%A1%9C%EC%A0%A0_%EA%B2%B0%ED%95%A9" title="할로젠 결합 – Korean" lang="ko" hreflang="ko" data-title="할로젠 결합" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Legame_ad_alogeno" title="Legame ad alogeno – Italian" lang="it" hreflang="it" data-title="Legame ad alogeno" data-language-autonym="Italiano" data-language-local-name="Italian" 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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Net attractive interaction involving one of the halogen elements</div> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, a <b>halogen bond</b> (<b>XB</b> or <b>HaB</b><sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>) occurs when there is evidence of a net attractive interaction between an <a href="/wiki/Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a> region associated with a <a href="/wiki/Halogen" title="Halogen">halogen</a> atom in a <a href="/wiki/Molecular_entity" title="Molecular entity">molecular entity</a> and a <a href="/wiki/Nucleophilic" class="mw-redirect" title="Nucleophilic">nucleophilic</a> region in another, or the same, molecular entity.<sup id="cite_ref-:0_2-0" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Like a <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bond</a>, the result is not a formal <a href="/wiki/Chemical_bond" title="Chemical bond">chemical bond</a>, but rather a strong <a href="/wiki/Electrostatics" title="Electrostatics">electrostatic</a> attraction.<sup id="cite_ref-Metrangolo_2005_3-0" class="reference"><a href="#cite_note-Metrangolo_2005-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Gilday_2015_4-0" class="reference"><a href="#cite_note-Gilday_2015-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Mathematically, the interaction can be decomposed in two terms: one describing an electrostatic, <a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">orbital-mixing</a> charge-transfer and another describing <a href="/w/index.php?title=Electron-cloud&action=edit&redlink=1" class="new" title="Electron-cloud (page does not exist)">electron-cloud</a> dispersion. Halogen bonds find application in <a href="/wiki/Supramolecular_chemistry" title="Supramolecular chemistry">supramolecular chemistry</a>;<sup id="cite_ref-Metrangolo_2005_3-1" class="reference"><a href="#cite_note-Metrangolo_2005-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Gilday_2015_4-1" class="reference"><a href="#cite_note-Gilday_2015-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-supramolecular2511_5-0" class="reference"><a href="#cite_note-supramolecular2511-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Drug_design" title="Drug design">drug design</a> and <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a>;<sup id="cite_ref-BioUses_6-0" class="reference"><a href="#cite_note-BioUses-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Cavallo_2016_7-0" class="reference"><a href="#cite_note-Cavallo_2016-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Crystal_engineering" title="Crystal engineering">crystal engineering</a><sup id="cite_ref-Cavallo_2016_7-1" class="reference"><a href="#cite_note-Cavallo_2016-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Liquid_crystal" title="Liquid crystal">liquid crystals</a>;<sup id="cite_ref-Metrangolo_2005_3-2" class="reference"><a href="#cite_note-Metrangolo_2005-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> and organic <a href="/wiki/Catalysis" title="Catalysis">catalysis</a>.<sup id="cite_ref-Cavallo_2016_7-2" class="reference"><a href="#cite_note-Cavallo_2016-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Definition">Definition</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen_bond&action=edit&section=1" title="Edit section: Definition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:IodoChlorineAmine.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/IodoChlorineAmine.jpg/105px-IodoChlorineAmine.jpg" decoding="async" width="105" height="168" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/IodoChlorineAmine.jpg/158px-IodoChlorineAmine.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cb/IodoChlorineAmine.jpg/210px-IodoChlorineAmine.jpg 2x" data-file-width="371" data-file-height="592" /></a><figcaption>Halogen bond in complex between <a href="/wiki/Iodine_monochloride" title="Iodine monochloride">iodine monochloride</a> and <a href="/wiki/Trimethylamine" title="Trimethylamine">trimethylamine</a>.</figcaption></figure> <p>Halogen bonds occur when a halogen atom is electrostatically attracted to a <a href="/wiki/Partial_charge" title="Partial charge">partial negative charge</a>. Necessarily, the atom must be covalently bonded in an <a href="/wiki/Antipodes" title="Antipodes">antipodal</a> <a href="/wiki/Sigma_bond" title="Sigma bond">σ-bond</a>; the electron concentration associated with that bond leaves a positively charged "hole" on the other side.<sup id="cite_ref-Hassel1970_8-0" class="reference"><a href="#cite_note-Hassel1970-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Although all halogens can theoretically participate in halogen bonds, the σ-hole shrinks if the electron cloud in question <a href="/wiki/Polarizability" title="Polarizability">polarizes poorly</a> or the halogen is so <a href="/wiki/Electronegativity" title="Electronegativity">electronegative</a> as to polarize the associated σ-bond.<sup id="cite_ref-Metrangolo_2005_3-3" class="reference"><a href="#cite_note-Metrangolo_2005-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Clark_2007_9-0" class="reference"><a href="#cite_note-Clark_2007-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Consequently halogen-bond propensity follows the trend<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>Note 1<span class="cite-bracket">]</span></a></sup> F < Cl < Br < I. </p><p>There is no clear distinction between halogen bonds and <a href="/wiki/Expanded_octet" class="mw-redirect" title="Expanded octet">expanded octet</a> <a href="/wiki/Bond_order" title="Bond order">partial bonds</a>; what is superficially a halogen bond may well turn out to be a full bond in an unexpectedly relevant <a href="/wiki/Resonance_structure" class="mw-redirect" title="Resonance structure">resonance structure</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Donor_characteristics">Donor characteristics</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen_bond&action=edit&section=2" title="Edit section: Donor characteristics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A halogen bond is almost <a href="/wiki/Collinearity" title="Collinearity">collinear</a> with the halogen atom's other, conventional bond, but the geometry of the electron-charge donor may be much more complex. </p> <ul><li>Multi-electron donors such as <a href="/wiki/Ether" title="Ether">ethers</a> and <a href="/wiki/Amine" title="Amine">amines</a> prefer halogen bonds collinear with the <a href="/wiki/Lone_pair" title="Lone pair">lone pair</a> and donor nucleus.</li> <li><a href="/wiki/Pyridine" title="Pyridine">Pyridine</a> derivatives tend to donate halogen bonds approximately coplanar with the ring, and the two C–N–X angles are about 120°.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Carbonyl_group" title="Carbonyl group">Carbonyl</a>, <a href="/wiki/Thioketone" title="Thioketone">thiocarbonyl-</a>, and selenocarbonyl groups, with a <a href="/wiki/Trigonal_planar_molecular_geometry" title="Trigonal planar molecular geometry">trigonal planar geometry</a> around the Lewis donor atom, can accept one or two halogen bonds.<sup id="cite_ref-Metrangolo_2008_17-0" class="reference"><a href="#cite_note-Metrangolo_2008-17"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup></li></ul> <p><a href="/wiki/Ion" title="Ion">Anions</a> are usually better halogen-bond acceptors than neutral species: the more dissociated an ion pair is, the stronger the halogen bond formed with the anion.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Comparison_to_other_bond-like_forces">Comparison to other bond-like forces</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen_bond&action=edit&section=3" title="Edit section: Comparison to other bond-like forces"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A parallel relationship can easily be drawn between halogen bonding and <a href="/wiki/Hydrogen_bonding" class="mw-redirect" title="Hydrogen bonding">hydrogen bonding</a>. Both interactions revolve around an <a href="/wiki/Electron_donor" title="Electron donor">electron donor</a>/<a href="/wiki/Electron_acceptor" title="Electron acceptor">electron acceptor</a> relationship, between a halogen-like atom and an <a href="/wiki/Electron_density" title="Electron density">electron-dense</a> one. But halogen bonding is both much stronger and more sensitive to direction than hydrogen bonding. A typical hydrogen bond has <a href="/wiki/Bond_energy" title="Bond energy">energy of formation</a> <span class="nowrap"><span data-sort-value="7004200000000000000♠"></span>20 kJ/mol</span>; known halogen <a href="/wiki/Bond_energy" title="Bond energy">bond energies</a> range from 10–200 kJ/mol.<sup id="cite_ref-Metrangolo_2008_17-1" class="reference"><a href="#cite_note-Metrangolo_2008-17"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>The σ-hole concept readily extends to pnictogen, chalcogen and aerogen bonds, corresponding to atoms of Groups <a href="/wiki/Pnictogen" title="Pnictogen">15</a>, <a href="/wiki/Chalcogen" title="Chalcogen">16</a> and <a href="/wiki/Aerogen" class="mw-redirect" title="Aerogen">18</a> (respectively).<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen_bond&action=edit&section=4" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Bromine-dioxane.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Bromine-dioxane.svg/303px-Bromine-dioxane.svg.png" decoding="async" width="303" height="65" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Bromine-dioxane.svg/455px-Bromine-dioxane.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/72/Bromine-dioxane.svg/606px-Bromine-dioxane.svg.png 2x" data-file-width="840" data-file-height="180" /></a><figcaption>Chains in the 1:1 adduct of 1,4-dioxane and bromine, the first crystallographic evidence of halogen bonding.</figcaption></figure> <p>In 1814, Jean-Jacques Colin discovered (to his surprise) that a mixture of dry gaseous ammonia and iodine formed a shiny, metallic-appearing liquid. Frederick Guthrie established the precise composition of the resulting I<sub>2</sub>···NH<sub>3</sub> complex fifty years later, but the physical processes underlying the molecular interaction remained mysterious until the development of <a href="/wiki/Robert_S._Mulliken" title="Robert S. Mulliken">Robert S. Mulliken</a>'s theory of inner-sphere and outer-sphere interactions.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> In Mulliken's categorization, the intermolecular interactions associated with small partial charges affect only the "inner sphere" of an atom's electron distribution; the electron redistribution associated with <a href="/wiki/Lewis_adduct" class="mw-redirect" title="Lewis adduct">Lewis adducts</a> affects the "outer sphere" instead.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Then, in 1954, <a href="/wiki/Odd_Hassel" title="Odd Hassel">Odd Hassel</a> fruitfully applied the distinction to rationalize the <a href="/wiki/X-ray_diffraction" title="X-ray diffraction">X-ray diffraction</a> patterns associated with a mixture of 1,4-dioxane and bromine.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> The patterns suggested that only 2.71 Å separated the dioxane <a href="/wiki/Oxygen" title="Oxygen">oxygen atoms</a> and bromine atoms, much closer than the sum (3.35 Å) of the atoms' van der Waals radii; and that the angle between the O−Br and Br−Br bond was about 180°. From these facts, Hassel concluded that halogen atoms are directly linked to electron pair donors in a direction with a bond direction that coincides with the axes of the orbitals of the lone pairs in the electron pair donor molecule.<sup id="cite_ref-Hassel1970_8-1" class="reference"><a href="#cite_note-Hassel1970-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> For this work, Hassel was awarded the 1969 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a>.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>Dumas and coworkers first coined the term "halogen bond" in 1978, during their investigations into complexes of CCl<sub>4</sub>, CBr<sub>4</sub>, SiCl<sub>4</sub>, and SiBr<sub>4</sub> with <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a>, <a href="/wiki/Tetrahydropyran" title="Tetrahydropyran">tetrahydropyran</a>, <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>, <a href="/wiki/Anisole" title="Anisole">anisole</a>, and <a href="/wiki/Di-n-butyl_ether" class="mw-redirect" title="Di-n-butyl ether">di-n-butyl ether</a> in organic solvents.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>However, it was not until the mid-1990s, that the nature and applications of the halogen bond began to be intensively studied. Through systematic and extensive <a href="/wiki/Microwave_spectroscopy" title="Microwave spectroscopy">microwave spectroscopy</a> of gas-phase halogen bond adducts, Legon and coworkers drew attention to the similarities between halogen-bonding and better-known hydrogen-bonding interactions.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>In 2007, computational calculations by Politzer and Murray showed that an anisotropic electron density distribution around the halogen nucleus — the "σ-hole"<sup id="cite_ref-Clark_2007_9-1" class="reference"><a href="#cite_note-Clark_2007-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> — underlay the high directionality of the halogen bond.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> This hole was then experimentally observed using <a href="/wiki/Kelvin_probe_force_microscope" title="Kelvin probe force microscope">Kelvin probe force microscopy</a>.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>In 2020, Kellett <i>et al.</i> showed that halogen bonds also have a π-covalent character similar to <a href="/wiki/Coordinate_covalent_bond" title="Coordinate covalent bond">metal coordination bonds</a>.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> In August 2023 the "π-hole" was too experimentally observed<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen_bond&action=edit&section=5" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Crystal_engineering">Crystal engineering</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen_bond&action=edit&section=6" title="Edit section: Crystal engineering"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Silsesquixane_halogen_bond.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Silsesquixane_halogen_bond.tif/lossy-page1-262px-Silsesquixane_halogen_bond.tif.jpg" decoding="async" width="262" height="221" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Silsesquixane_halogen_bond.tif/lossy-page1-393px-Silsesquixane_halogen_bond.tif.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Silsesquixane_halogen_bond.tif/lossy-page1-524px-Silsesquixane_halogen_bond.tif.jpg 2x" data-file-width="718" data-file-height="605" /></a><figcaption>Br···O halogen bonds observed in the 3D crystal structure of certain silsesquioxanes.<sup id="cite_ref-Janeta_2017_32-0" class="reference"><a href="#cite_note-Janeta_2017-32"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>The strength and directionality of halogen bonds are a key tool in the discipline of <a href="/wiki/Crystal_engineering" title="Crystal engineering">crystal engineering</a>, which attempts to shape crystal structures through close control of intermolecular interactions.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Halogen bonds can stabilize copolymers<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> or induce <a href="/wiki/Mesophase" title="Mesophase">mesomorphism</a> in otherwise isotropic <a href="/wiki/Liquid" title="Liquid">liquids</a>.<sup id="cite_ref-Nguyen_2004_36-0" class="reference"><a href="#cite_note-Nguyen_2004-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Indeed, halogen bond-induced liquid crystalline phases are known in both alkoxystilbazoles<sup id="cite_ref-Nguyen_2004_36-1" class="reference"><a href="#cite_note-Nguyen_2004-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Silsesquioxane" title="Silsesquioxane">silsesquioxanes</a> (pictured).<sup id="cite_ref-Janeta_2017_32-1" class="reference"><a href="#cite_note-Janeta_2017-32"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Alternatively, the <a href="/wiki/Steric_effects" title="Steric effects">steric sensitivity</a> of halogen bonds can cause bulky molecules to crystallize into <a href="/wiki/Porous_material" class="mw-redirect" title="Porous material">porous structures</a>; in one notable case, halogen bonds between <a href="/wiki/Iodine" title="Iodine">iodine</a> and <a href="/wiki/Aromatic_compound" title="Aromatic compound">aromatic</a> <a href="/wiki/Pi_Orbitals" class="mw-redirect" title="Pi Orbitals">π-orbitals</a> caused molecules to crystallize into a pattern that was nearly 40% <a href="/wiki/Void_(composites)" title="Void (composites)">void</a>.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Controlled_polymerization">Controlled polymerization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen_bond&action=edit&section=7" title="Edit section: Controlled polymerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div><p> Conjugated polymers offer the tantalizing possibility of organic molecules with a manipulable <a href="/wiki/Electronic_band_structure" title="Electronic band structure">electronic band structure</a>, but current methods for production have an uncontrolled <a href="/wiki/Topological_polymers" title="Topological polymers">topology</a>. Sun, Lauher, and Goroff discovered that certain <a href="/wiki/Amide" title="Amide">amides</a> ensure a linear polymerization of <a href="/wiki/Poly(diiododiacetylene)" class="mw-redirect" title="Poly(diiododiacetylene)">poly(diiododiacetylene)</a>. The underlying mechanism is a self-organization of the amides via hydrogen bonds that then transfers to the diiododiacetylene monomers via halogen bonds. Although pure diiododiacetylene crystals do not <a href="/wiki/Polymerization" title="Polymerization">polymerize</a> spontaneously, the halogen-bond induced organization is sufficiently strong that the cocrystals do spontaneously polymerize.<sup id="cite_ref-polysomething_38-0" class="reference"><a href="#cite_note-polysomething-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><div style="clear:both;" class=""></div> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 365px"> <div class="thumb" style="width: 360px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Monomerand6.jpg" class="mw-file-description" title="The catalyst-monomer cocrystal. Units repeat every 5.25 Å and are oriented at 51.3˚."><img alt="The catalyst-monomer cocrystal. Units repeat every 5.25 Å and are oriented at 51.3˚." src="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Monomerand6.jpg/251px-Monomerand6.jpg" decoding="async" width="251" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Monomerand6.jpg/377px-Monomerand6.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Monomerand6.jpg/502px-Monomerand6.jpg 2x" data-file-width="700" data-file-height="335" /></a></span></div> <div class="gallerytext">The catalyst-monomer cocrystal. Units repeat every 5.25 Å and are oriented at 51.3˚.</div> </li> <li class="gallerybox" style="width: 365px"> <div class="thumb" style="width: 360px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:PIDA.jpg" class="mw-file-description" title="Post-polymerization crystal structure: the oxygen atom (purple) forms a hydrogen bond (blue dashed line) and a weak halogen bond with the polymer's iodine substituents. Iodine may also form a halogen bond with the terminal nitriles (red dashed line)."><img alt="Post-polymerization crystal structure: the oxygen atom (purple) forms a hydrogen bond (blue dashed line) and a weak halogen bond with the polymer's iodine substituents. Iodine may also form a halogen bond with the terminal nitriles (red dashed line)." src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/PIDA.jpg/197px-PIDA.jpg" decoding="async" width="197" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/PIDA.jpg/295px-PIDA.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/06/PIDA.jpg/393px-PIDA.jpg 2x" data-file-width="635" data-file-height="388" /></a></span></div> <div class="gallerytext">Post-polymerization crystal structure: the oxygen atom (purple) forms a hydrogen bond (blue dashed line) and a weak halogen bond with the polymer's iodine substituents. Iodine may also form a halogen bond with the terminal nitriles (red dashed line).</div> </li> </ul> <div class="mw-heading mw-heading3"><h3 id="Biological_macromolecules">Biological macromolecules</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen_bond&action=edit&section=8" title="Edit section: Biological macromolecules"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:IDD594_protein-inhibitor_complex.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/IDD594_protein-inhibitor_complex.jpg/220px-IDD594_protein-inhibitor_complex.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/IDD594_protein-inhibitor_complex.jpg/330px-IDD594_protein-inhibitor_complex.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/IDD594_protein-inhibitor_complex.jpg/440px-IDD594_protein-inhibitor_complex.jpg 2x" data-file-width="720" data-file-height="540" /></a><figcaption> IDD 594 binding to human <a href="/wiki/Aldose_reductase" title="Aldose reductase">aldose reductase</a>: a short Br−O halogen bond contributes to inhibitor potency.<sup id="cite_ref-0.66A_39-0" class="reference"><a href="#cite_note-0.66A-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup></figcaption></figure><p>Most biological macromolecules contain few or no halogen atoms. But when molecules do contain halogens, halogen bonds are often essential to understanding molecular <a href="/wiki/Conformational_isomerism" title="Conformational isomerism">conformation</a>. Computational studies suggest that known halogenated <a href="/wiki/Nucleobase" class="mw-redirect" title="Nucleobase">nucleobases</a> form halogen bonds with <a href="/wiki/Oxygen" title="Oxygen">oxygen</a>, <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>, or <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> <i>in vitro</i>. Interestingly, oxygen atoms typically do not attract halogens with their <a href="/wiki/Lone_pair" title="Lone pair">lone pairs</a>, but rather the <a href="/wiki/Pi_Orbitals" class="mw-redirect" title="Pi Orbitals">π</a> electrons in the <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a> or <a href="/wiki/Amide_group" class="mw-redirect" title="Amide group">amide group</a>.<sup id="cite_ref-BioUses_6-1" class="reference"><a href="#cite_note-BioUses-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Halogen bonding can be significant in <a href="/wiki/Drug_design" title="Drug design">drug design</a> as well. For example, inhibitor <a href="/w/index.php?title=IDD_594&action=edit&redlink=1" class="new" title="IDD 594 (page does not exist)">IDD 594</a> binds to human <a href="/wiki/Aldose_reductase" title="Aldose reductase">aldose reductase</a> through a bromine halogen bond, as shown in the figure. The molecules fail to bind to each other if similar <a href="/wiki/Aldehyde_reductase" class="mw-redirect" title="Aldehyde reductase">aldehyde reductase</a> replaces the enzyme, or <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> replaces the drug halogen, because the variant geometries inhibit the halogen bond.<sup id="cite_ref-0.66A_39-1" class="reference"><a href="#cite_note-0.66A-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen_bond&action=edit&section=9" title="Edit section: Notes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div style="clear:left;" class=""></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text">Although <a href="/wiki/Periodic_table#Period_1" title="Periodic table">hydrogen is sometimes considered a halogen</a>, convention excludes <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonds</a> from the category of halogen bonds. For a complete analysis, see <a href="#Comparison_to_other_bond-like_forces">§ Comparison to other bond-like forces</a>.</span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen_bond&action=edit&section=10" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFVaradwajVaradwajMarquesYamashita2024" class="citation journal cs1">Varadwaj, Pradeep R.; Varadwaj, Arpita; Marques, Helder M.; Yamashita, Koichi (2024-07-03). <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/10.1021/acs.cgd.4c00228">"Definition of the Halogen Bond (IUPAC Recommendations 2013): A Revisit"</a>. <i>Crystal Growth & Design</i>. <b>24</b> (13): 5494–5525. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.cgd.4c00228">10.1021/acs.cgd.4c00228</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1528-7483">1528-7483</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Crystal+Growth+%26+Design&rft.atitle=Definition+of+the+Halogen+Bond+%28IUPAC+Recommendations+2013%29%3A+A+Revisit&rft.volume=24&rft.issue=13&rft.pages=5494-5525&rft.date=2024-07-03&rft_id=info%3Adoi%2F10.1021%2Facs.cgd.4c00228&rft.issn=1528-7483&rft.aulast=Varadwaj&rft.aufirst=Pradeep+R.&rft.au=Varadwaj%2C+Arpita&rft.au=Marques%2C+Helder+M.&rft.au=Yamashita%2C+Koichi&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2F10.1021%2Facs.cgd.4c00228&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHalogen+bond" class="Z3988"></span></span> </li> <li id="cite_note-:0-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-:0_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDesirajuHoKlooLegon2013" class="citation journal cs1">Desiraju GR, Ho PS, Kloo L, Legon AC, Marquardt R, Metrangolo P, et al. 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"Preparation of poly(diiododiacetylene), an ordered conjugated polymer of carbon and iodine". <i>Science</i>. <b>312</b> (5776): 1030–1034. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2006Sci...312.1030S">2006Sci...312.1030S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.1124621">10.1126/science.1124621</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16709780">16709780</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:36045120">36045120</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Preparation+of+poly%28diiododiacetylene%29%2C+an+ordered+conjugated+polymer+of+carbon+and+iodine&rft.volume=312&rft.issue=5776&rft.pages=1030-1034&rft.date=2006-05&rft_id=info%3Adoi%2F10.1126%2Fscience.1124621&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A36045120%23id-name%3DS2CID&rft_id=info%3Apmid%2F16709780&rft_id=info%3Abibcode%2F2006Sci...312.1030S&rft.aulast=Sun&rft.aufirst=A&rft.au=Lauher%2C+JW&rft.au=Goroff%2C+NS&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHalogen+bond" class="Z3988"></span></span> </li> <li id="cite_note-0.66A-39"><span class="mw-cite-backlink">^ <a href="#cite_ref-0.66A_39-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-0.66A_39-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHowardSanishviliCachauMitschler2004" class="citation journal cs1">Howard EI, Sanishvili R, Cachau RE, Mitschler A, Chevrier B, Barth P, et al. (June 2004). <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fprot.20015">"Ultrahigh resolution drug design I: details of interactions in human aldose reductase-inhibitor complex at 0.66 A"</a>. <i>Proteins</i>. <b>55</b> (4): 792–804. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fprot.20015">10.1002/prot.20015</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15146478">15146478</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:38388856">38388856</a>. <q>The electrostatic interaction between the Br atom of the inhibitor and the OG of Thr 113 has an unusually short distance of 2.973(4) Å. The short contact between Br and Thr 113 OG explains the selectivity of IDD 594 towards AR, because in aldehyde reductase the Thr residue is replaced by Tyr....The IDD 594-Br/Thr 113-OG interaction also contributes to the potency of the inhibitor. Other halogens, such as chlorine, cannot engage in a similar interaction (due to its lower polarizability).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proteins&rft.atitle=Ultrahigh+resolution+drug+design+I%3A+details+of+interactions+in+human+aldose+reductase-inhibitor+complex+at+0.66+A&rft.volume=55&rft.issue=4&rft.pages=792-804&rft.date=2004-06&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A38388856%23id-name%3DS2CID&rft_id=info%3Apmid%2F15146478&rft_id=info%3Adoi%2F10.1002%2Fprot.20015&rft.aulast=Howard&rft.aufirst=EI&rft.au=Sanishvili%2C+R&rft.au=Cachau%2C+RE&rft.au=Mitschler%2C+A&rft.au=Chevrier%2C+B&rft.au=Barth%2C+P&rft.au=Lamour%2C+V&rft.au=Van+Zandt%2C+M&rft.au=Sibley%2C+E&rft.au=Bon%2C+C&rft.au=Moras%2C+D&rft.au=Schneider%2C+TR&rft.au=Joachimiak%2C+A&rft.au=Podjarny%2C+A&rft_id=https%3A%2F%2Fdoi.org%2F10.1002%252Fprot.20015&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHalogen+bond" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen_bond&action=edit&section=11" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>An early review: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBent1968" class="citation journal cs1">Bent, H. A. (1968). "Structural Chemistry of Donor-Acceptor Interactions". <i>Chem. Rev</i>. <b>68</b> (5): 587–648. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr60255a003">10.1021/cr60255a003</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Rev.&rft.atitle=Structural+Chemistry+of+Donor-Acceptor+Interactions&rft.volume=68&rft.issue=5&rft.pages=587-648&rft.date=1968&rft_id=info%3Adoi%2F10.1021%2Fcr60255a003&rft.aulast=Bent&rft.aufirst=H.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHalogen+bond" class="Z3988"></span></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline 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class="navbox-group" style="width:1%"><a href="/wiki/Covalent_bond" title="Covalent bond">Covalent</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electron_deficiency" title="Electron deficiency">Electron deficiency</a> <ul><li><a href="/wiki/Three-center_two-electron_bond" title="Three-center two-electron bond">3c–2e</a></li> <li><a href="/wiki/Four-center_two-electron_bond" title="Four-center two-electron bond">4c–2e</a></li> <li><a href="/wiki/Eight-center_two-electron_bond" class="mw-redirect" title="Eight-center two-electron bond">8c–2e</a></li></ul></li> <li><a href="/wiki/Hypervalent_molecule" title="Hypervalent molecule">Hypervalence</a> <ul><li><a href="/wiki/Three-center_four-electron_bond" title="Three-center four-electron bond">3c–4e</a></li></ul></li> <li><a href="/wiki/Agostic_interaction" title="Agostic interaction">Agostic</a></li> <li><a href="/wiki/Bent_bond" title="Bent bond">Bent</a></li> <li><a href="/wiki/Coordinate_covalent_bond" title="Coordinate covalent bond">Coordinate (dipolar)</a></li> <li><a href="/wiki/Pi_backbonding" title="Pi backbonding">Pi backbond</a></li> <li><a href="/wiki/Metal%E2%80%93ligand_multiple_bond" title="Metal–ligand multiple bond">Metal–ligand multiple bond</a></li> <li><a href="/wiki/Charge-shift_bond" title="Charge-shift bond">Charge-shift</a></li> <li><a href="/wiki/Hapticity" title="Hapticity">Hapticity</a></li> <li><a href="/wiki/Conjugated_system" title="Conjugated system">Conjugation</a></li> <li><a href="/wiki/Hyperconjugation" title="Hyperconjugation">Hyperconjugation</a></li> <li><a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a> <ul><li><a href="/wiki/Homoaromaticity" title="Homoaromaticity">homo</a></li> <li><a href="/wiki/Bicycloaromaticity" title="Bicycloaromaticity">bicyclo</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Metallic_bonding" title="Metallic bonding">Metallic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Metal_aromaticity" title="Metal aromaticity">Metal aromaticity</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ionic_bonding" title="Ionic bonding">Ionic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li class="mw-empty-elt"></li></ul> </div></td></tr></tbody></table><div></div></td><td class="noviewer navbox-image" rowspan="4" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/File:Ligatio-covalens.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/200px-Ligatio-covalens.svg.png" decoding="async" width="200" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/300px-Ligatio-covalens.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/400px-Ligatio-covalens.svg.png 2x" data-file-width="597" data-file-height="265" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Chemfm_carbon_monoxide_3_1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/200px-Chemfm_carbon_monoxide_3_1.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/300px-Chemfm_carbon_monoxide_3_1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/400px-Chemfm_carbon_monoxide_3_1.svg.png 2x" data-file-width="99" data-file-height="56" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Pi-Bond.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/200px-Pi-Bond.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/300px-Pi-Bond.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/400px-Pi-Bond.svg.png 2x" data-file-width="1920" data-file-height="1080" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intermolecular_force" title="Intermolecular force">Intermolecular</a><br />(weak)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Van_der_Waals_force" title="Van der Waals force">Van der Waals<br />forces</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/London_dispersion_force" title="London dispersion force">London dispersion</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_bond" title="Hydrogen bond">Hydrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Low-barrier_hydrogen_bond" title="Low-barrier hydrogen bond">Low-barrier</a></li> <li><a href="/wiki/Resonance-assisted_hydrogen_bond" class="mw-redirect" title="Resonance-assisted hydrogen bond">Resonance-assisted</a></li> <li><a href="/wiki/Symmetric_hydrogen_bond" title="Symmetric hydrogen bond">Symmetric</a></li> <li><a href="/wiki/Dihydrogen_bond" title="Dihydrogen bond">Dihydrogen bonds</a></li> <li><a href="/wiki/C%E2%80%93H%C2%B7%C2%B7%C2%B7O_interaction" title="C–H···O interaction">C–H···O interaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Non-covalent_interactions" class="mw-redirect" title="Non-covalent interactions">Noncovalent</a><br />other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mechanically_interlocked_molecular_architectures" title="Mechanically interlocked molecular architectures">Mechanical</a></li> <li><a class="mw-selflink selflink">Halogen</a></li> <li><a href="/wiki/Chalcogen_bond" title="Chalcogen bond">Chalcogen</a></li> <li><a href="/wiki/Metallophilic_interaction" title="Metallophilic interaction">Metallophilic</a> (<a href="/wiki/Aurophilicity" title="Aurophilicity">aurophilic</a>)</li> <li><a href="/wiki/Intercalation_(chemistry)" title="Intercalation (chemistry)">Intercalation</a></li> <li><a href="/wiki/Stacking_(chemistry)" title="Stacking (chemistry)">Stacking</a></li> <li><a href="/wiki/Cation%E2%80%93pi_interaction" class="mw-redirect" title="Cation–pi interaction">Cation–pi</a></li> <li><a href="/wiki/Cation%E2%80%93pi_interaction#Anion–π_interaction" class="mw-redirect" title="Cation–pi interaction">Anion–pi</a></li> <li><a href="/wiki/Salt_bridge_(protein_and_supramolecular)" title="Salt bridge (protein and supramolecular)">Salt bridge</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bond_cleavage" title="Bond cleavage">Bond cleavage</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Heterolysis_(chemistry)" title="Heterolysis (chemistry)">Heterolysis</a></li> <li><a href="/wiki/Homolysis_(chemistry)" title="Homolysis (chemistry)">Homolysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Electron_counting" title="Electron counting">Electron counting</a> rules</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a> <ul><li><a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a></li> <li><a href="/wiki/Baird%27s_rule" title="Baird's rule">Baird's rule</a></li> <li><a href="/wiki/M%C3%B6bius_aromaticity" title="Möbius aromaticity">Möbius</a></li> <li><a href="/wiki/Spherical_aromaticity" title="Spherical aromaticity">spherical</a></li></ul></li> <li><a href="/wiki/Polyhedral_skeletal_electron_pair_theory" title="Polyhedral skeletal electron pair theory">Polyhedral skeletal electron pair theory</a></li> <li><a href="/wiki/Jemmis_mno_rules" title="Jemmis mno rules">Jemmis mno rules</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img 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