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<li id="toc-Historically_important_compounds_where_the_ligands_are_described_with_hapticity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Historically_important_compounds_where_the_ligands_are_described_with_hapticity"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Historically important compounds where the ligands are described with hapticity</span> </div> </a> <ul id="toc-Historically_important_compounds_where_the_ligands_are_described_with_hapticity-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Examples" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Examples"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Examples</span> </div> </a> <button aria-controls="toc-Examples-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon 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id="toc-Hapticity_vs._denticity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Hapticity_vs._denticity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Hapticity vs. denticity</span> </div> </a> <ul id="toc-Hapticity_vs._denticity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hapticity_and_fluxionality" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Hapticity_and_fluxionality"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Hapticity and fluxionality</span> </div> </a> <ul id="toc-Hapticity_and_fluxionality-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> 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Available in 19 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-19" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">19 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AA%D9%84%D8%A7%D9%85%D8%B3_(%D9%83%D9%8A%D9%85%D9%8A%D8%A7%D8%A1)" title="تلامس (كيمياء) – Arabic" lang="ar" hreflang="ar" data-title="تلامس (كيمياء)" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Hapti%C4%8Dnost" title="Haptičnost – Bosnian" lang="bs" hreflang="bs" data-title="Haptičnost" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Hapticitat" title="Hapticitat – Catalan" lang="ca" hreflang="ca" data-title="Hapticitat" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Hapticita" title="Hapticita – Czech" lang="cs" hreflang="cs" data-title="Hapticita" 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/Haptizit%C3%A4t" title="Haptizität – German" lang="de" hreflang="de" data-title="Haptizität" 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/Hapticidad" title="Hapticidad – Spanish" lang="es" hreflang="es" data-title="Hapticidad" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%DB%8C%D9%88%D9%86%D8%AF%D9%BE%D9%88%D8%B4%DB%8C" title="پیوندپوشی – Persian" lang="fa" hreflang="fa" data-title="پیوندپوشی" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Hapticit%C3%A9" title="Hapticité – French" lang="fr" hreflang="fr" data-title="Hapticité" 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%A9%ED%86%A0%EC%88%98" title="합토수 – Korean" lang="ko" hreflang="ko" data-title="합토수" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B9%E0%A5%88%E0%A4%AA%E0%A5%8D%E0%A4%9F%E0%A4%BF%E0%A4%B8%E0%A4%BF%E0%A4%9F%E0%A5%80" title="हैप्टिसिटी – Hindi" lang="hi" hreflang="hi" data-title="हैप्टिसिटी" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Apticit%C3%A0" title="Apticità – Italian" lang="it" hreflang="it" data-title="Apticità" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Hapticiteit" title="Hapticiteit – Dutch" lang="nl" hreflang="nl" data-title="Hapticiteit" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%8F%E3%83%97%E3%83%88%E6%95%B0" title="ハプト数 – Japanese" lang="ja" hreflang="ja" data-title="ハプト数" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Hapticitate" title="Hapticitate – Romanian" lang="ro" hreflang="ro" data-title="Hapticitate" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Hapti%C4%8Dnost" title="Haptičnost – Serbian" lang="sr" hreflang="sr" data-title="Haptičnost" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Hapti%C4%8Dnost" title="Haptičnost – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Haptičnost" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Haptisuus" title="Haptisuus – Finnish" lang="fi" hreflang="fi" data-title="Haptisuus" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D0%B0%D0%BF%D1%82%D0%B8%D1%87%D0%BD%D1%96%D1%81%D1%82%D1%8C" title="Гаптичність – Ukrainian" lang="uk" hreflang="uk" data-title="Гаптичність" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%93%88%E6%99%AE%E6%89%98%E6%95%B8" title="哈普托數 – Chinese" lang="zh" hreflang="zh" data-title="哈普托數" data-language-autonym="中文" data-language-local-name="Chinese" 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Number of contiguous atoms in a ligand that bond to the central atom in a coordination complex</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the co-ordination of a ligand to a central atom. For the sense of touch in technology, see <a href="/wiki/Haptic_technology" title="Haptic technology">Haptic technology</a>.</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ferrocene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ferrocene.svg/150px-Ferrocene.svg.png" decoding="async" width="150" height="253" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ferrocene.svg/225px-Ferrocene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ferrocene.svg/300px-Ferrocene.svg.png 2x" data-file-width="103" data-file-height="174" /></a><figcaption><a href="/wiki/Ferrocene" title="Ferrocene">Ferrocene</a> contains two η<sup>5</sup>-<a href="/wiki/Cyclopentadienyl_ligand" class="mw-redirect" title="Cyclopentadienyl ligand">cyclopentadienyl ligands</a></figcaption></figure> <p>In <a href="/wiki/Coordination_chemistry" class="mw-redirect" title="Coordination chemistry">coordination chemistry</a>, <b>hapticity</b> is the <a href="/wiki/Coordination_complex" title="Coordination complex">coordination</a> of a <a href="/wiki/Ligand" title="Ligand">ligand</a> to a metal center via an uninterrupted and contiguous series of <a href="/wiki/Atom" title="Atom">atoms</a>.<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> The hapticity of a ligand is described with the Greek letter <a href="/wiki/Eta_(letter)" class="mw-redirect" title="Eta (letter)">η</a> ('eta'). For example, η<sup>2</sup> describes a ligand that coordinates through 2 contiguous atoms. In general the η-notation only applies when multiple atoms are coordinated (otherwise the <a href="/wiki/Denticity" title="Denticity">κ-notation</a> is used). In addition, if the ligand coordinates through multiple atoms that are <em>not</em> contiguous then this is considered <a href="/wiki/Denticity" title="Denticity">denticity</a><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> (not hapticity), and the κ-notation is used once again.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> When naming complexes care should be taken not to confuse η with <a href="/wiki/Mu_(letter)" title="Mu (letter)">μ</a> ('mu'), which relates to <a href="/wiki/Bridging_ligand" title="Bridging ligand">bridging ligands</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <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=Hapticity&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The need for additional nomenclature for organometallic compounds became apparent in the mid-1950s when Dunitz, <a href="/wiki/Leslie_Orgel" title="Leslie Orgel">Orgel</a>, and Rich described the structure of the "<a href="/wiki/Sandwich_compound" title="Sandwich compound">sandwich complex</a>" <a href="/wiki/Ferrocene" title="Ferrocene">ferrocene</a> by <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> where an <a href="/wiki/Iron" title="Iron">iron</a> atom is <i>"sandwiched"</i> between two parallel <a href="/wiki/Cyclopentadienyl" title="Cyclopentadienyl">cyclopentadienyl</a> rings. <a href="/wiki/F._Albert_Cotton" title="F. Albert Cotton">Cotton</a> later proposed the term <i>hapticity</i> derived from the adjectival prefix hapto (from the Greek <i>haptein</i>, to fasten, denoting contact or combination) placed before the name of the olefin,<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> where the Greek letter η (eta) is used to denote the number of contiguous atoms of a ligand that bind to a metal center. The term is usually employed to refer to ligands containing extended π-systems or where <a href="/wiki/Agostic_complex" class="mw-redirect" title="Agostic complex">agostic bonding</a> is not obvious from the formula. </p> <div class="mw-heading mw-heading3"><h3 id="Historically_important_compounds_where_the_ligands_are_described_with_hapticity">Historically important compounds where the ligands are described with hapticity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hapticity&action=edit&section=2" title="Edit section: Historically important compounds where the ligands are described with hapticity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Ferrocene" title="Ferrocene">Ferrocene</a>: bis(η<sup>5</sup>-<a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">cyclopentadienyl</a>)<a href="/wiki/Iron" title="Iron">iron</a></li> <li><a href="/wiki/Uranocene" title="Uranocene">Uranocene</a>: bis(η<sup>8</sup>-1,3,5,7-<a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">cyclooctatetraene</a>)<a href="/wiki/Uranium" title="Uranium">uranium</a></li> <li>W(CO)<sub>3</sub>(PPr<sup>i</sup><sub>3</sub>)<sub>2</sub>(η<sup>2</sup>-H<sub>2</sub>): the first compound to be synthesized with a <a href="/wiki/Dihydrogen_complex" title="Dihydrogen complex">dihydrogen</a> ligand.<sup id="cite_ref-Kubas1_8-0" class="reference"><a href="#cite_note-Kubas1-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kubas2_9-0" class="reference"><a href="#cite_note-Kubas2-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li> <li>IrCl(CO)[P(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>]<sub>2</sub>(η<sup>2</sup>-O<sub>2</sub>): the <a href="/wiki/Dioxygen_complex" class="mw-redirect" title="Dioxygen complex">dioxygen</a> derivative which forms reversibly upon oxygenation of <a href="/wiki/Vaska%27s_complex" title="Vaska's complex">Vaska's complex</a>.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hapticity&action=edit&section=3" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The η-notation is encountered in many coordination compounds: </p> <ul><li>Side-on bonding of molecules containing σ-bonds like <a href="/wiki/Dihydrogen_complex" title="Dihydrogen complex">H<sub>2</sub></a>: <ul><li>W(CO)<sub>3</sub>(P<sup>i</sup>Pr<sub>3</sub>)<sub>2</sub>(η<sup>2</sup>-H<sub>2</sub>)<sup id="cite_ref-Kubas1_8-1" class="reference"><a href="#cite_note-Kubas1-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kubas2_9-1" class="reference"><a href="#cite_note-Kubas2-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li></ul></li> <li>Side-on bonded ligands containing multiple bonded atoms, e.g. <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> in <a href="/wiki/Zeise%27s_salt" title="Zeise's salt">Zeise's salt</a> or with <a href="/wiki/Fullerene_ligand" class="mw-redirect" title="Fullerene ligand">fullerene</a>, which is bonded through donation of the π-bonding electrons: <ul><li>K[PtCl<sub>3</sub>(η<sup>2</sup>-C<sub>2</sub>H<sub>4</sub>)]<sup>.</sup><a href="/wiki/Water_of_crystallization" title="Water of crystallization">H<sub>2</sub>O</a></li></ul></li> <li>Related complexes containing bridging π-ligands: <ul><li>(μ-η<sup>2</sup>:η<sup>2</sup>-<a href="/wiki/Acetylene" title="Acetylene">C<sub>2</sub>H<sub>2</sub></a>)Co<sub>2</sub>(CO)<sub>6</sub> and (<a href="/wiki/Cp*" class="mw-redirect" title="Cp*">Cp*</a><sub>2</sub><a href="/wiki/Samarium" title="Samarium">Sm</a>)<sub>2</sub>(μ-η<sup>2</sup>:η<sup>2</sup>-<a href="/wiki/Nitrogen" title="Nitrogen">N<sub>2</sub></a>)<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></li> <li><a href="/wiki/Dioxygen_complex" class="mw-redirect" title="Dioxygen complex">Dioxygen</a> in bis{(trispyrazolylborato)copper(II)}(μ-η<sup>2</sup>:η<sup>2</sup>-O<sub>2</sub>),</li></ul></li></ul> <dl><dd><dl><dd>Note that with some <a href="/wiki/Bridging_ligand" title="Bridging ligand">bridging ligands</a>, an alternative bridging mode is observed, e.g. κ<sup>1</sup>,κ<sup>1</sup>, like in (Me<sub>3</sub>SiCH<sub>2</sub>)<sub>3</sub>V(μ-N<sub>2</sub>-κ<sup>1</sup>(N),κ<sup>1</sup>(N′))V(CH<sub>2</sub>SiMe<sub>3</sub>)<sub>3</sub> contains a bridging dinitrogen molecule, where the molecule is end-on coordinated to the two metal centers (see <a href="#Hapticity_vs._denticity">hapticity vs. denticity</a>).</dd></dl></dd></dl> <ul><li>The bonding of π-bonded species can be extended over several atoms, e.g. in <a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allyl</a>, <a href="/wiki/Butadiene" title="Butadiene">butadiene</a> ligands, but also in <a href="/wiki/Cyclopentadienyl_complex" title="Cyclopentadienyl complex">cyclopentadienyl</a> or <a href="/wiki/Benzene" title="Benzene">benzene</a> rings can share their electrons.</li> <li>Apparent violations of the <a href="/wiki/18-electron_rule" title="18-electron rule">18-electron rule</a> sometimes are explicable in compounds with unusual hapticities: <ul><li>The 18-VE complex (η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)Fe(η<sup>1</sup>-C<sub>5</sub>H<sub>5</sub>)(CO)<sub>2</sub> contains one η<sup>5</sup> bonded cyclopentadienyl, and one η<sup>1</sup> bonded cyclopentadienyl.</li> <li><a href="/wiki/Redox" title="Redox">Reduction</a> of the 18-VE compound [Ru(η<sup>6</sup>-C<sub>6</sub>Me<sub>6</sub>)<sub>2</sub>]<sup>2+</sup> (where both aromatic rings are bonded in an η<sup>6</sup>-coordination), results in another 18-VE compound: [Ru(η<sup>6</sup>-C<sub>6</sub>Me<sub>6</sub>)(η<sup>4</sup>-C<sub>6</sub>Me<sub>6</sub>)].</li></ul></li> <li>Examples of polyhapto coordinated heterocyclic and inorganic rings: Cr(η<sup>5</sup>-C<sub>4</sub>H<sub>4</sub>S)(CO)<sub>3</sub> contains the <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> heterocycle <a href="/wiki/Thiophene" title="Thiophene">thiophene</a> and Cr(η<sup>6</sup>-B<sub>3</sub>N<sub>3</sub>Me<sub>6</sub>)(CO)<sub>3</sub> contains a coordinated inorganic ring (B<sub>3</sub>N<sub>3</sub> ring).</li></ul> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:MOKLAZ.search14.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/MOKLAZ.search14.png/220px-MOKLAZ.search14.png" decoding="async" width="220" height="236" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/MOKLAZ.search14.png/330px-MOKLAZ.search14.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/MOKLAZ.search14.png/440px-MOKLAZ.search14.png 2x" data-file-width="1200" data-file-height="1289" /></a><figcaption>Structure of (η<sup>3</sup>-C<sub>5</sub>Me<sub>5</sub>)<sub>2</sub>Mo(N)(N<sub>3</sub>).<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Electrons_donated_by_"π-ligands"_versus_hapticity"><span id="Electrons_donated_by_.22.CF.80-ligands.22_versus_hapticity"></span>Electrons donated by "π-ligands" versus hapticity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hapticity&action=edit&section=4" title="Edit section: Electrons donated by "π-ligands" versus hapticity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="sortable wikitable"> <tbody><tr> <th>Ligand</th> <th>Electrons<br />contributed<br />(neutral counting)</th> <th>Electrons<br />contributed<br />(ionic counting) </th></tr> <tr> <td>η<sup>1</sup>-<a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allyl</a></td> <td>1</td> <td>2 </td></tr> <tr> <td>η<sup>3</sup>-<a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allyl</a><br />cyclopropenyl</td> <td>3</td> <td>4 </td></tr> <tr> <td>η<sup>2</sup>-<a href="/wiki/Butadiene" title="Butadiene">butadiene</a></td> <td>2</td> <td>2 </td></tr> <tr> <td>η<sup>4</sup>-<a href="/wiki/Butadiene" title="Butadiene">butadiene</a></td> <td>4</td> <td>4 </td></tr> <tr> <td>η<sup>1</sup>-<a href="/wiki/Cyclopentadienyl" title="Cyclopentadienyl">cyclopentadienyl</a></td> <td>1</td> <td>2 </td></tr> <tr> <td>η<sup>3</sup>-<a href="/wiki/Cyclopentadienyl" title="Cyclopentadienyl">cyclopentadienyl</a></td> <td>3</td> <td>4 </td></tr> <tr> <td>η<sup>5</sup>-<a href="/wiki/Cyclopentadienyl" title="Cyclopentadienyl">cyclopentadienyl</a><br />pentadienyl<br />cyclohexadienyl</td> <td>5</td> <td>6 </td></tr> <tr> <td>η<sup>2</sup>-<a href="/wiki/Benzene" title="Benzene">benzene</a></td> <td>2</td> <td>2 </td></tr> <tr> <td>η<sup>4</sup>-<a href="/wiki/Benzene" title="Benzene">benzene</a></td> <td>4</td> <td>4 </td></tr> <tr> <td>η<sup>6</sup>-<a href="/wiki/Benzene" title="Benzene">benzene</a></td> <td>6</td> <td>6 </td></tr> <tr> <td>η<sup>7</sup>-<a href="/wiki/Tropylium_cation" title="Tropylium cation">cycloheptatrienyl</a></td> <td>7</td> <td>6 or 10 </td></tr> <tr> <td>η<sup>8</sup>-<a href="/wiki/Cyclooctatetraenyl" class="mw-redirect" title="Cyclooctatetraenyl">cyclooctatetraenyl</a></td> <td>8</td> <td>10 </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Changes_in_hapticity">Changes in hapticity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hapticity&action=edit&section=5" title="Edit section: Changes in hapticity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The hapticity of a ligand can change in the course of a reaction.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> E.g. in a redox reaction: </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:EofRu(bz)2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/EofRu%28bz%292.png/300px-EofRu%28bz%292.png" decoding="async" width="300" height="149" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/EofRu%28bz%292.png/450px-EofRu%28bz%292.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8f/EofRu%28bz%292.png/600px-EofRu%28bz%292.png 2x" data-file-width="801" data-file-height="399" /></a><figcaption></figcaption></figure></dd></dl> <p>Here one of the η<sup>6</sup>-benzene rings changes to a η<sup>4</sup>-benzene. </p><p>Similarly hapticity can change during a substitution reaction: </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Eta5-eta3-eta5_Reaction(Colors).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Eta5-eta3-eta5_Reaction%28Colors%29.png/400px-Eta5-eta3-eta5_Reaction%28Colors%29.png" decoding="async" width="400" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Eta5-eta3-eta5_Reaction%28Colors%29.png/600px-Eta5-eta3-eta5_Reaction%28Colors%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/82/Eta5-eta3-eta5_Reaction%28Colors%29.png/800px-Eta5-eta3-eta5_Reaction%28Colors%29.png 2x" data-file-width="1669" data-file-height="411" /></a><figcaption></figcaption></figure></dd></dl> <p>Here the η<sup>5</sup>-cyclopentadienyl changes to an η<sup>3</sup>-cyclopentadienyl, giving room on the metal for an extra 2-electron donating ligand 'L'. Removal of one molecule of CO and again donation of two more electrons by the cyclopentadienyl ligand restores the η<sup>5</sup>-cyclopentadienyl. The so-called <a href="/wiki/Indenyl_effect" class="mw-redirect" title="Indenyl effect">indenyl effect</a> also describes changes in hapticity in a substitution reaction. </p> <div class="mw-heading mw-heading2"><h2 id="Hapticity_vs._denticity">Hapticity vs. denticity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hapticity&action=edit&section=6" title="Edit section: Hapticity vs. denticity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hapticity must be distinguished from <a href="/wiki/Denticity" title="Denticity">denticity</a>. Polydentate ligands coordinate via multiple coordination sites within the ligand. In this case the coordinating atoms are identified using the κ-notation, as for example seen in coordination of <a href="/wiki/1,2-bis(diphenylphosphino)ethane" class="mw-redirect" title="1,2-bis(diphenylphosphino)ethane">1,2-bis(diphenylphosphino)ethane</a> (Ph<sub>2</sub>PCH<sub>2</sub>CH<sub>2</sub>PPh<sub>2</sub>), to <a href="/wiki/Nickel(II)_chloride" title="Nickel(II) chloride">NiCl<sub>2</sub></a> as dichloro[ethane-1,2-diylbis(diphenylphosphane)-κ<sup>2</sup>P]nickel(II). If the coordinating atoms are contiguous (connected to each other), the η-notation is used, as e.g. in <a href="/wiki/Titanocene_dichloride" title="Titanocene dichloride">titanocene dichloride</a>: dichlorobis(η<sup>5</sup>-2,4-cyclopentadien-1-yl)titanium.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Hapticity_and_fluxionality">Hapticity and fluxionality</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hapticity&action=edit&section=7" title="Edit section: Hapticity and fluxionality"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Molecules with polyhapto ligands are often <a href="/wiki/Fluxional_molecule" title="Fluxional molecule">fluxional</a>, also known as stereochemically non-rigid. Two classes of fluxionality are prevalent for organometallic complexes of polyhapto ligands: </p> <ul><li>Case 1, typically: when the hapticity value is less than the number of sp<sup>2</sup> carbon atoms. In such situations, the metal will often migrate from carbon to carbon, maintaining the same net hapticity. The η<sup>1</sup>-C<sub>5</sub>H<sub>5</sub> ligand in (η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)Fe( η<sup>1</sup>-C<sub>5</sub>H<sub>5</sub>)(CO)<sub>2</sub> rearranges rapidly in solution such that Fe binds alternatingly to each carbon atom in the η<sup>1</sup>-C<sub>5</sub>H<sub>5</sub> ligand. This reaction is <a href="/wiki/Degenerate_energy_levels" title="Degenerate energy levels">degenerate</a> and, in the jargon of <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, it is an example of a <a href="/wiki/Sigmatropic_rearrangement" class="mw-redirect" title="Sigmatropic rearrangement">sigmatropic rearrangement</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2010)">citation needed</span></a></i>]</sup> A related example is <a href="/wiki/Bis(cyclooctatetraene)iron" title="Bis(cyclooctatetraene)iron">Bis(cyclooctatetraene)iron</a>, in which the η<sup>4</sup>- and η<sup>6</sup>-C<sub>8</sub>H<sub>8</sub> rings interconvert.</li> <li>Case 2, typically: complexes containing cyclic polyhapto ligands with maximized hapticity. Such ligands tend to rotate. A famous example is <a href="/wiki/Ferrocene" title="Ferrocene">ferrocene</a>,<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Fe(η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>, wherein the Cp rings rotate with a low <a href="/wiki/Activation_energy" title="Activation energy">energy barrier</a> about the <a href="/wiki/Principal_axis_(crystallography)" class="mw-redirect" title="Principal axis (crystallography)">principal axis</a> of the molecule that "skewers" each ring (see <a href="/wiki/Rotational_symmetry" title="Rotational symmetry">rotational symmetry</a>). This "ring torsion" explains, inter alia, why only one isomer can be isolated for Fe(η<sup>5</sup>-C<sub>5</sub>H<sub>4</sub>Br)<sub>2</sub> since the torsional barrier is very low.</li></ul> <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=Hapticity&action=edit&section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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 mw-references-columns"><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"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/H01881.html">η (eta or hapto) <i>in inorganic nomenclature</i></a>". <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><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.H01881">10.1351/goldbook.H01881</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/D01594.html">denticity</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.D01594">10.1351/goldbook.D01594</a></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/K03366.html">κ (kappa) <i>in inorganic nomenclature</i></a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.K03366">10.1351/goldbook.K03366</a></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/B00741.html">bridging ligand</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.B00741">10.1351/goldbook.B00741</a></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/M03659.html">µ- (mu) <i>in inorganic nomenclature</i></a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.M03659">10.1351/goldbook.M03659</a></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJ._DunitzL._OrgelA._Rich1956" class="citation journal cs1">J. Dunitz; L. Orgel; A. Rich (1956). <a rel="nofollow" class="external text" href="https://doi.org/10.1107%2FS0365110X56001091">"The crystal structure of ferrocene"</a>. <i>Acta Crystallographica</i>. <b>9</b> (4): 373–5. <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/10.1107%2FS0365110X56001091">10.1107/S0365110X56001091</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Crystallographica&rft.atitle=The+crystal+structure+of+ferrocene&rft.volume=9&rft.issue=4&rft.pages=373-5&rft.date=1956&rft_id=info%3Adoi%2F10.1107%2FS0365110X56001091&rft.au=J.+Dunitz&rft.au=L.+Orgel&rft.au=A.+Rich&rft_id=https%3A%2F%2Fdoi.org%2F10.1107%252FS0365110X56001091&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHapticity" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFF._A._Cotton1968" class="citation journal cs1"><a href="/wiki/F._Albert_Cotton" title="F. Albert Cotton">F. A. Cotton</a> (1968). "Proposed nomenclature for olefin-metal and other organometallic complexes". <i><a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a></i> <b>90</b> (22): 6230–6232. <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%2Fja01024a059">10.1021/ja01024a059</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Proposed+nomenclature+for+olefin-metal+and+other+organometallic+complexes&rft.volume=90&rft.issue=22&rft.pages=6230-6232&rft.date=1968&rft_id=info%3Adoi%2F10.1021%2Fja01024a059&rft.au=F.+A.+Cotton&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHapticity" class="Z3988"></span></span> </li> <li id="cite_note-Kubas1-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Kubas1_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Kubas1_8-1"><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="CITEREFKubas1988" class="citation journal cs1">Kubas, Gregory J. (March 1988). "Molecular hydrogen complexes: coordination of a σ bond to transition metals". <i><a href="/wiki/Accounts_of_Chemical_Research" title="Accounts of Chemical Research">Accounts of Chemical Research</a></i>. <b>21</b> (3): 120–128. <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%2Far00147a005">10.1021/ar00147a005</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Accounts+of+Chemical+Research&rft.atitle=Molecular+hydrogen+complexes%3A+coordination+of+a+%CF%83+bond+to+transition+metals&rft.volume=21&rft.issue=3&rft.pages=120-128&rft.date=1988-03&rft_id=info%3Adoi%2F10.1021%2Far00147a005&rft.aulast=Kubas&rft.aufirst=Gregory+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHapticity" class="Z3988"></span></span> </li> <li id="cite_note-Kubas2-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Kubas2_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Kubas2_9-1"><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="CITEREFKubas2001" class="citation book cs1">Kubas, Gregory J. (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=SSn_OQAACAAJ"><i>Metal Dihydrogen and σ-Bond Complexes - Structure, Theory, and Reactivity</i></a> (1 ed.). 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Sutton (1993). "Organometallic diazo compounds". <i><a href="/wiki/Chem._Rev." class="mw-redirect" title="Chem. Rev.">Chem. Rev.</a></i> <b>93</b> (3): 995–1022. <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%2Fcr00019a008">10.1021/cr00019a008</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=Organometallic+diazo+compounds&rft.volume=93&rft.issue=3&rft.pages=995-1022&rft.date=1993&rft_id=info%3Adoi%2F10.1021%2Fcr00019a008&rft.au=D.+Sutton&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHapticity" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJun_Ho_ShinBrian_M._BridgewaterDavid_G._ChurchillMu-Hyun_Baik2001" class="citation journal cs1">Jun Ho Shin; Brian M. Bridgewater; David G. Churchill; Mu-Hyun Baik; Richard A. Friesner; Gerard Parkin (2001). "An Experimental and Computational Analysis of the Formation of the Terminal Nitrido Complex (η<sup>3</sup>-Cp*)<sub>2</sub>Mo(N)(N<sub>3</sub>) by Elimination of N<sub>2</sub> from Cp*<sub>2</sub>Mo(N<sub>3</sub>)<sub>2</sub>: The Barrier to Elimination Is Strongly Influenced by the exo versus endo Configuration of the Azide Ligand". <i>J. Am. Chem. Soc</i>. <b>123</b> (41): 10111–10112. <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%2Fja011416v">10.1021/ja011416v</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=An+Experimental+and+Computational+Analysis+of+the+Formation+of+the+Terminal+Nitrido+Complex+%28%CE%B7%3Csup%3E3%3C%2Fsup%3E-Cp%2A%29%3Csub%3E2%3C%2Fsub%3EMo%28N%29%28N%3Csub%3E3%3C%2Fsub%3E%29+by+Elimination+of+N%3Csub%3E2%3C%2Fsub%3E+from+Cp%2A%3Csub%3E2%3C%2Fsub%3EMo%28N%3Csub%3E3%3C%2Fsub%3E%29%3Csub%3E2%3C%2Fsub%3E%3A+The+Barrier+to+Elimination+Is+Strongly+Influenced+by+the+exo+versus+endo+Configuration+of+the+Azide+Ligand&rft.volume=123&rft.issue=41&rft.pages=10111-10112&rft.date=2001&rft_id=info%3Adoi%2F10.1021%2Fja011416v&rft.au=Jun+Ho+Shin&rft.au=Brian+M.+Bridgewater&rft.au=David+G.+Churchill&rft.au=Mu-Hyun+Baik&rft.au=Richard+A.+Friesner&rft.au=Gerard+Parkin&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHapticity" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHuttnerLangeFischer1971" class="citation journal cs1">Huttner, Gottfried; Lange, Siegfried; <a href="/wiki/Ernst_Otto_Fischer" title="Ernst Otto Fischer">Fischer, Ernst O.</a> (1971). "Molecular Structure of Bis(Hexamethylbenzene)-Ruthenium(0)". <i><a href="/wiki/Angewandte_Chemie_International_Edition_in_English" class="mw-redirect" title="Angewandte Chemie International Edition in English">Angewandte Chemie International Edition in English</a></i>. <b>10</b> (8): 556–557. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.197105561">10.1002/anie.197105561</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition+in+English&rft.atitle=Molecular+Structure+of+Bis%28Hexamethylbenzene%29-Ruthenium%280%29&rft.volume=10&rft.issue=8&rft.pages=556-557&rft.date=1971&rft_id=info%3Adoi%2F10.1002%2Fanie.197105561&rft.aulast=Huttner&rft.aufirst=Gottfried&rft.au=Lange%2C+Siegfried&rft.au=Fischer%2C+Ernst+O.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHapticity" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="http://www.iupac.org/reports/provisional/abstract04/RB-prs310804/Chap9-3.04.pdf">"IR-9.2.4.1 Coordination Compounds: Describing the Constitution of Coordination Compounds: Specifying donor atoms: General"</a> <span class="cs1-format">(PDF)</span>. <a rel="nofollow" class="external text" href="http://old.iupac.org/reports/provisional/abstract04/connelly_310804.html"><i>Nomenclature of Inorganic Chemistry – Recommendations 1990 (the 'Red Book')</i></a> (Draft March 2004 ed.). <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a>. 2004. p. 16.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=IR-9.2.4.1+Coordination+Compounds%3A+Describing+the+Constitution+of+Coordination+Compounds%3A+Specifying+donor+atoms%3A+General&rft.btitle=Nomenclature+of+Inorganic+Chemistry+%E2%80%93+Recommendations+1990+%28the+%27Red+Book%27%29&rft.pages=16&rft.edition=Draft+March+2004&rft.pub=IUPAC&rft.date=2004&rft_id=http%3A%2F%2Fwww.iupac.org%2Freports%2Fprovisional%2Fabstract04%2FRB-prs310804%2FChap9-3.04.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHapticity" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBunker1965" class="citation journal cs1">Bunker, P.R. (1965). "The Vibrational Selection Rules and Torsional Barrier of Ferrocene". <i>Molecular Physics</i>. <b>9</b> (3): 247–255. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F00268976500100321">10.1080/00268976500100321</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Physics&rft.atitle=The+Vibrational+Selection+Rules+and+Torsional+Barrier+of+Ferrocene&rft.volume=9&rft.issue=3&rft.pages=247-255&rft.date=1965&rft_id=info%3Adoi%2F10.1080%2F00268976500100321&rft.aulast=Bunker&rft.aufirst=P.R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHapticity" class="Z3988"></span></span> </li> </ol></div></div> <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 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title="Ligand field theory">Ligand field theory</a></li> <li><a href="/wiki/18-electron_rule" title="18-electron rule">18-electron rule</a></li> <li><a href="/wiki/D_electron_count" title="D electron count">d electron count</a></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/Isolobal_principle" title="Isolobal principle">Isolobal principle</a></li> <li><a href="/wiki/Pi_backbonding" title="Pi backbonding">π backbonding</a></li> <li><a href="/wiki/Dewar%E2%80%93Chatt%E2%80%93Duncanson_model" title="Dewar–Chatt–Duncanson model">Dewar–Chatt–Duncanson model</a></li> <li><a class="mw-selflink selflink">Hapticity</a></li> <li><a href="/wiki/Spin_states_(d_electrons)" title="Spin states (d electrons)">spin states</a></li> <li><a href="/wiki/Agostic_interaction" title="Agostic interaction">Agostic interaction</a></li> <li><a href="/wiki/Metal%E2%80%93ligand_multiple_bond" title="Metal–ligand multiple bond">Metal–ligand multiple bond</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</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/Oxidative_addition" title="Oxidative addition">Oxidative addition</a> / <a href="/wiki/Reductive_elimination" title="Reductive elimination">reductive elimination</a></li> <li><a href="/wiki/Migratory_insertion" title="Migratory insertion">Migratory insertion</a></li> <li><a href="/wiki/Beta-Hydride_elimination" class="mw-redirect" title="Beta-Hydride elimination">β-hydride elimination</a></li> <li><a href="/wiki/Transmetalation" title="Transmetalation">Transmetalation</a></li> <li><a href="/wiki/Carbometalation" title="Carbometalation">Carbometalation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Types of compounds</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/Gilman_reagent" title="Gilman reagent">Gilman reagents</a></li> <li><a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a></li> <li><a href="/wiki/Cyclopentadienyl_complex" title="Cyclopentadienyl complex">Cyclopentadienyl complexes</a></li> <li><a href="/wiki/Transition_metal_indenyl_complex" title="Transition metal indenyl complex">Transition metal indenyl complexes</a></li> <li><a href="/wiki/Transition_metal_fullerene_complex" title="Transition metal fullerene complex">Transition metal fullerene complexes</a></li> <li><a href="/wiki/Metallocene" title="Metallocene">Metallocenes</a></li> <li><a href="/wiki/Metal_tetranorbornyl" title="Metal tetranorbornyl">Metal tetranorbornyls</a></li> <li><a href="/wiki/Sandwich_compound" title="Sandwich compound">Sandwich compounds</a></li> <li><a href="/wiki/Half_sandwich_compound" title="Half sandwich compound">Half sandwich compounds</a></li> <li><a href="/wiki/Transition_metal_acyl_complexes" title="Transition metal acyl complexes">Transition metal acyl complexes</a></li> <li><a href="/wiki/Transition_metal_carbene_complex" title="Transition metal carbene complex">Transition metal carbene complexes</a></li> <li><a href="/wiki/Transition_metal_carbyne_complex" title="Transition metal carbyne complex">Transition metal carbyne complexes</a></li> <li><a href="/wiki/Transition_metal_alkene_complex" title="Transition metal alkene complex">Transition metal alkene complexes</a></li> <li><a href="/wiki/Transition_metal_alkyne_complex" title="Transition metal alkyne complex">Transition metal alkyne complexes</a></li> <li><a href="/wiki/Transition-metal_allyl_complex" title="Transition-metal allyl complex">Transition-metal allyl complexes</a></li> <li><a href="/wiki/Metal_carbido_complex" title="Metal carbido complex">Transition metal carbides</a></li> <li><a href="/wiki/Arene_complexes_of_univalent_gallium,_indium,_and_thallium" title="Arene complexes of univalent gallium, indium, and thallium">Arene complexes of univalent gallium, indium, and thallium</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Applications</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/Carbonylation" title="Carbonylation">Carbonylation</a></li> <li><a href="/wiki/Cativa_process" title="Cativa process">Cativa process</a></li> <li><a href="/wiki/Grignard_reaction" title="Grignard reaction">Grignard reaction</a></li> <li><a href="/wiki/Monsanto_process" title="Monsanto process">Monsanto process</a></li> <li><a href="/wiki/Olefin_metathesis" title="Olefin metathesis">Olefin metathesis</a></li> <li><a href="/wiki/Shell_higher_olefin_process" title="Shell higher olefin process">Shell higher olefin process</a></li> <li><a href="/wiki/Ziegler%E2%80%93Natta_catalyst" title="Ziegler–Natta catalyst">Ziegler–Natta process</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related branches of <a href="/wiki/Chemistry" title="Chemistry">chemistry</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/Organic_chemistry" title="Organic chemistry">Organic chemistry</a></li> <li><a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">Inorganic chemistry</a></li> <li><a href="/wiki/Bioinorganic_chemistry" title="Bioinorganic chemistry">Bioinorganic chemistry</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" 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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 class="mw-selflink selflink">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 href="/wiki/Halogen_bond" title="Halogen bond">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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