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class="vector-toc-numb">2</span> <span>Characteristics of agostic bonds</span> </div> </a> <button aria-controls="toc-Characteristics_of_agostic_bonds-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Characteristics of agostic bonds subsection</span> </button> <ul id="toc-Characteristics_of_agostic_bonds-sublist" class="vector-toc-list"> <li id="toc-Strength_of_bond" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Strength_of_bond"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Strength of bond</span> </div> </a> <ul id="toc-Strength_of_bond-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Related_bonding_interactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Related_bonding_interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Related bonding interactions</span> </div> </a> <button aria-controls="toc-Related_bonding_interactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Related bonding interactions subsection</span> </button> <ul id="toc-Related_bonding_interactions-sublist" class="vector-toc-list"> <li id="toc-Anagostic_bonds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Anagostic_bonds"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Anagostic bonds</span> </div> </a> <ul id="toc-Anagostic_bonds-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Function" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Function"> <div class="vector-toc-text"> <span 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mw-first-heading"><span class="mw-page-title-main">Agostic interaction</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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href="https://bs.wikipedia.org/wiki/Agosti%C4%8Dna_interakcija" title="Agostična interakcija – Bosnian" lang="bs" hreflang="bs" data-title="Agostična interakcija" 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/Interacci%C3%B3_ag%C3%B2stica" title="Interacció agòstica – Catalan" lang="ca" hreflang="ca" data-title="Interacció agòstica" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Agostische_Wechselwirkung" title="Agostische Wechselwirkung – German" lang="de" hreflang="de" data-title="Agostische Wechselwirkung" 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/Interacci%C3%B3n_ag%C3%B3stica" title="Interacción agóstica – Spanish" lang="es" hreflang="es" data-title="Interacción agóstica" 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/Interaction_agostique" title="Interaction agostique – French" lang="fr" hreflang="fr" data-title="Interaction agostique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Interaksi_agostik" title="Interaksi agostik – Indonesian" lang="id" hreflang="id" data-title="Interaksi agostik" 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href="https://sr.wikipedia.org/wiki/Agosti%C4%8Dka_interakcija" title="Agostička interakcija – Serbian" lang="sr" hreflang="sr" data-title="Agostička interakcija" 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/Agosti%C4%8Dka_interakcija" title="Agostička interakcija – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Agostička interakcija" 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-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%B3%D0%BE%D1%81%D1%82%D0%B8%D1%87%D0%BD%D0%B0_%D0%B2%D0%B7%D0%B0%D1%94%D0%BC%D0%BE%D0%B4%D1%96%D1%8F" title="Агостична взаємодія – Ukrainian" lang="uk" hreflang="uk" 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The present address (URL) is a <a href="/wiki/Help:Permanent_link" title="Help:Permanent link">permanent link</a> to this version.</b></p><div id="revision-info-current-plain" style="display: none;">Revision as of 06:24, 11 August 2024 by <a href="/wiki/User:Alsosaid1987" class="mw-userlink" title="User:Alsosaid1987" data-mw-revid="1239737449"><bdi>Alsosaid1987</bdi></a> <span class="mw-usertoollinks">(<a href="/wiki/User_talk:Alsosaid1987" class="mw-usertoollinks-talk" title="User talk:Alsosaid1987">talk</a> | <a href="/wiki/Special:Contributions/Alsosaid1987" class="mw-usertoollinks-contribs" title="Special:Contributions/Alsosaid1987">contribs</a>)</span></div></div><div id="mw-revision-nav">(<a href="/w/index.php?title=Agostic_interaction&diff=prev&oldid=1239737449" title="Agostic interaction">diff</a>) <a href="/w/index.php?title=Agostic_interaction&direction=prev&oldid=1239737449" title="Agostic interaction">← Previous revision</a> | Latest revision (diff) | Newer revision → (diff)</div></div></div></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">Formation of a 3-center 2-electron bond between a transition metal and C–H bond</div> <p>In <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>, <b>agostic interaction</b> refers to the intramolecular interaction of a <a href="/wiki/Saturated_and_unsaturated_compounds#Organometallic_chemistry" title="Saturated and unsaturated compounds">coordinatively-unsaturated</a> <a href="/wiki/Transition_metal" title="Transition metal">transition metal</a> with an appropriately situated <a href="/wiki/Carbon%E2%80%93hydrogen_bond" title="Carbon–hydrogen bond">C−H bond</a> on one of its ligands. The interaction is the result of two electrons involved in the C−H bond interaction with an empty <a href="/wiki/Atomic_orbital" title="Atomic orbital">d-orbital</a> of the transition metal, resulting in a <a href="/wiki/Three-center_two-electron_bond" title="Three-center two-electron bond">three-center two-electron bond</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> It is a special case of a <a href="/wiki/Sigma_complex" title="Sigma complex">C–H sigma complex</a>. Historically, agostic complexes were the first examples of C–H sigma complexes to be observed spectroscopically and crystallographically, due to intramolecular interactions being particularly favorable and more often leading to robust complexes. Many catalytic transformations involving <a href="/wiki/Oxidative_addition" title="Oxidative addition">oxidative addition</a> and <a href="/wiki/Reductive_elimination" title="Reductive elimination">reductive elimination</a> are proposed to proceed via <a href="/wiki/Reaction_intermediate" title="Reaction intermediate">intermediates</a> featuring agostic interactions. Agostic interactions are observed throughout <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a> in <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a>, <a href="/wiki/Alkylidene" class="mw-redirect" title="Alkylidene">alkylidene</a>, and polyenyl ligands. </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=Agostic_interaction&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The term agostic, derived from the <a href="/wiki/Ancient_Greek" title="Ancient Greek">Ancient Greek</a> word for "to hold close to oneself", was coined by <a href="/wiki/Maurice_Brookhart" title="Maurice Brookhart">Maurice Brookhart</a> and <a href="/wiki/Malcolm_Green_(chemist)" title="Malcolm Green (chemist)">Malcolm Green</a>, on the suggestion of the <a href="/wiki/Classicist" class="mw-redirect" title="Classicist">classicist</a> <a href="/wiki/Jasper_Griffin" title="Jasper Griffin">Jasper Griffin</a>, to describe this and many other interactions between a transition metal and a <a href="/wiki/Carbon%E2%80%93hydrogen_bond" title="Carbon–hydrogen bond">C−H bond</a>. Often such agostic interactions involve alkyl or aryl groups that are held close to the metal center through an additional σ-bond.<sup id="cite_ref-Brook_2-0" class="reference"><a href="#cite_note-Brook-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><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> </p><p>Short interactions between hydrocarbon substituents and coordinatively unsaturated metal complexes have been noted since the 1960s. For example, in tris(<a href="/wiki/Triphenylphosphine" title="Triphenylphosphine">triphenylphosphine</a>) ruthenium dichloride, a short interaction is observed between the <a href="/wiki/Ruthenium" title="Ruthenium">ruthenium</a>(II) center and a hydrogen atom on the ortho position of one of the nine phenyl rings.<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> Complexes of <a href="/wiki/Borohydride" title="Borohydride">borohydride</a> are described as using the <a href="/wiki/Three-center_two-electron_bond" title="Three-center two-electron bond">three-center two-electron bonding</a> model. </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:AgostKubas.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/AgostKubas.png/200px-AgostKubas.png" decoding="async" width="200" height="218" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/AgostKubas.png/300px-AgostKubas.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cf/AgostKubas.png/400px-AgostKubas.png 2x" data-file-width="410" data-file-height="446" /></a><figcaption>Mo(<a href="/wiki/Tricyclohexylphosphine" title="Tricyclohexylphosphine">PCy<sub>3</sub></a>)<sub>2</sub>(CO)<sub>3</sub>, featuring an agostic interaction</figcaption></figure> <p>The nature of the interaction was foreshadowed in main group chemistry in the structural chemistry of <a href="/wiki/Trimethylaluminium" title="Trimethylaluminium">trimethylaluminium</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Characteristics_of_agostic_bonds">Characteristics of agostic bonds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Agostic_interaction&action=edit&section=2" title="Edit section: Characteristics of agostic bonds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Agostic interactions are best demonstrated by <a href="/wiki/Crystallography" title="Crystallography">crystallography</a>. <a href="/wiki/Neutron_diffraction" title="Neutron diffraction">Neutron diffraction</a> data have shown that C−H and M┄H bond distances are 5-20% longer than expected for isolated metal hydride and hydrocarbons. The distance between the metal and the hydrogen is typically 1.8–2.3 <a href="/wiki/%C3%85ngstr%C3%B6m" class="mw-redirect" title="Ångström">Å</a>, and the M┄H−C angle is in the range of 90°–140°. The presence of a <sup>1</sup>H <a href="/wiki/NMR" class="mw-redirect" title="NMR">NMR</a> signal that is shifted upfield from that of a normal aryl or alkane, often to the region normally assigned to <a href="/wiki/Hydride" title="Hydride">hydride</a> ligands. The coupling constant <sup>1</sup><i>J</i><sub>CH</sub> is typically lowered to 70–100 Hz versus the 125 Hz expected for a normal sp<sup>3</sup> carbon–hydrogen bond. </p> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:MLHGtiag.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/MLHGtiag.png/170px-MLHGtiag.png" decoding="async" width="170" height="161" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/MLHGtiag.png/255px-MLHGtiag.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7d/MLHGtiag.png/340px-MLHGtiag.png 2x" data-file-width="622" data-file-height="590" /></a><figcaption>Structure of (C<sub>2</sub>H<sub>5</sub>)TiCl<sub>3</sub>(<a href="/wiki/Dmpe" class="mw-redirect" title="Dmpe">dmpe</a>), highlighting an agostic interaction between the methyl group and the Ti(IV) center.<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></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Strength_of_bond">Strength of bond</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Agostic_interaction&action=edit&section=3" title="Edit section: Strength of bond"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>On the basis of experimental and <a href="/wiki/Computational_chemistry" title="Computational chemistry">computational</a> studies, the stabilization arising from an agostic interaction is estimated to be 10–15 kcal/mol. Recent calculations using <a href="/wiki/Compliance_Constants" class="mw-redirect" title="Compliance Constants">compliance constants</a> point to a weaker stabilisation (<10 kcal/mol).<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> Thus, agostic interactions are stronger than most <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonds</a>. Agostic bonds sometimes play a role in catalysis by increasing 'rigidity' in transition states. For instance, in <a href="/wiki/Ziegler%E2%80%93Natta_catalysis" class="mw-redirect" title="Ziegler–Natta catalysis">Ziegler–Natta catalysis</a> the highly electrophilic metal center has agostic interactions with the growing polymer chain. This increased rigidity influences the stereoselectivity of the polymerization process. </p> <div class="mw-heading mw-heading2"><h2 id="Related_bonding_interactions">Related bonding interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Agostic_interaction&action=edit&section=4" title="Edit section: Related bonding interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Cp%27Mn(CO)2(HSiPh3).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Cp%27Mn%28CO%292%28HSiPh3%29.png/170px-Cp%27Mn%28CO%292%28HSiPh3%29.png" decoding="async" width="170" height="156" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Cp%27Mn%28CO%292%28HSiPh3%29.png/255px-Cp%27Mn%28CO%292%28HSiPh3%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Cp%27Mn%28CO%292%28HSiPh3%29.png/340px-Cp%27Mn%28CO%292%28HSiPh3%29.png 2x" data-file-width="468" data-file-height="429" /></a><figcaption>A <a href="/wiki/Transition_metal_silane_complexes" class="mw-redirect" title="Transition metal silane complexes">sigma complex</a> derived from (MeC<sub>5</sub>H<sub>4</sub>)Mn(CO)<sub>3</sub> and triphenylsilane.<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></figcaption></figure><p>The term agostic is reserved to describe two-electron, three-center bonding interactions between carbon, hydrogen, and a metal. Two-electron three-center bonding is clearly implicated in the complexation of H<sub>2</sub>, e.g., in W(CO)<sub>3</sub>(PCy<sub>3</sub>)<sub>2</sub>H<sub>2</sub>, which is closely related to the agostic complex shown in the figure.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Silane" title="Silane">Silane</a> binds to metal centers often via agostic-like, three-centered Si┄H−M interactions. Because these interactions do not include carbon, however, they are not classified as agostic. </p><div class="mw-heading mw-heading3"><h3 id="Anagostic_bonds">Anagostic bonds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Agostic_interaction&action=edit&section=5" title="Edit section: Anagostic bonds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Certain M┄H−C interactions are not classified as agostic but are described by the term <i>anagostic</i>. Anagostic interactions are more electrostatic in character. In terms of structures of anagostic interactions, the M┄H distances and M┄H−C angles fall into the ranges 2.3–2.9 Å and 110°–170°, respectively.<sup id="cite_ref-Brook_2-1" class="reference"><a href="#cite_note-Brook-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Function">Function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Agostic_interaction&action=edit&section=6" title="Edit section: Function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Agostic interactions serve a key function in <a href="/wiki/Alkene#Polymerization" title="Alkene">alkene polymerization</a> and <a href="/wiki/Stereochemistry" title="Stereochemistry">stereochemistry</a>, as well as <a href="/wiki/Migratory_insertion" title="Migratory insertion">migratory insertion</a>. </p> <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=Agostic_interaction&action=edit&section=7" 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 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"><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. 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Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/AT06984.html">agostic interaction</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.AT06984">10.1351/goldbook.AT06984</a></span> </li> <li id="cite_note-Brook-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Brook_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Brook_2-1"><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="CITEREFBrookhartGreen1983" class="citation journal cs1"><a href="/wiki/Maurice_Brookhart" title="Maurice Brookhart">Brookhart, Maurice</a>; <a href="/wiki/Malcolm_Green_(chemist)" title="Malcolm Green (chemist)">Green, Malcolm L. 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Soc., Dalton Trans.</i> (8): 1629. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fdt9860001629">10.1039/dt9860001629</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Chem.+Soc.%2C+Dalton+Trans.&rft.atitle=Evidence+for+Carbon%E2%80%93Hydrogen%E2%80%93Titanium+Interactions%3A+Synthesis+and+Crystal+Structures+of+the+Agostic+alkyls+%5BTiCl%3Csub%3E3%3C%2Fsub%3E%28Me%3Csub%3E2%3C%2Fsub%3EPCH%3Csub%3E2%3C%2Fsub%3ECH%3Csub%3E2%3C%2Fsub%3EPMe%3Csub%3E2%3C%2Fsub%3E%29R%5D+%28R+%3D+Et+or+Me%29&rft.issue=8&rft.pages=1629&rft.date=1986&rft_id=info%3Adoi%2F10.1039%2Fdt9860001629&rft.au=Z.+Dawoodi&rft.au=M.+L.+H.+Green&rft.au=V.+S.+B.+Mtetwa&rft.au=K.+Prout&rft.au=A.+J.+Schultz&rft.au=J.+M.+Williams&rft.au=T.+F.+Koetzle&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1230034&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAgostic+interaction" class="Z3988"></span></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="CITEREFVon_FrantziusStreubelBrandhorstGrunenberg2006" class="citation journal cs1">Von Frantzius, Gerd; Streubel, Rainer; Brandhorst, Kai; Grunenberg, Jörg (2006). "How Strong is an Agostic Bond? Direct Assessment of Agostic Interactions Using the Generalized Compliance Matrix". <i>Organometallics</i>. <b>25</b> (1): 118–121. <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%2Fom050489a">10.1021/om050489a</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organometallics&rft.atitle=How+Strong+is+an+Agostic+Bond%3F+Direct+Assessment+of+Agostic+Interactions+Using+the+Generalized+Compliance+Matrix&rft.volume=25&rft.issue=1&rft.pages=118-121&rft.date=2006&rft_id=info%3Adoi%2F10.1021%2Fom050489a&rft.aulast=Von+Frantzius&rft.aufirst=Gerd&rft.au=Streubel%2C+Rainer&rft.au=Brandhorst%2C+Kai&rft.au=Grunenberg%2C+J%C3%B6rg&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAgostic+interaction" 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="CITEREFNikonov,_G._I.2005" class="citation journal cs1">Nikonov, G. I. (2005). "Recent Advances in Nonclassical Interligand SiH Interactions". <i>Adv. Organomet. Chem</i>. Advances in Organometallic Chemistry. <b>53</b>: 217–309. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0065-3055%2805%2953006-5">10.1016/s0065-3055(05)53006-5</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780120311538" title="Special:BookSources/9780120311538"><bdi>9780120311538</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Adv.+Organomet.+Chem.&rft.atitle=Recent+Advances+in+Nonclassical+Interligand+SiH+Interactions&rft.volume=53&rft.pages=217-309&rft.date=2005&rft_id=info%3Adoi%2F10.1016%2Fs0065-3055%2805%2953006-5&rft.isbn=9780120311538&rft.au=Nikonov%2C+G.+I.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAgostic+interaction" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKubas2001" class="citation book cs1">Kubas, G. J. (2001). <i>Metal Dihydrogen and σ-Bond Complexes</i>. New York: Kluwer Academic. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-306-46465-2" title="Special:BookSources/978-0-306-46465-2"><bdi>978-0-306-46465-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Metal+Dihydrogen+and+%CF%83-Bond+Complexes&rft.place=New+York&rft.pub=Kluwer+Academic&rft.date=2001&rft.isbn=978-0-306-46465-2&rft.aulast=Kubas&rft.aufirst=G.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAgostic+interaction" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBragaGrepioniTedescoBiradha1997" class="citation journal cs1">Braga, D.; Grepioni, F.; Tedesco, E.; Biradha, K.; Desiraju, G. R. (1997). "Hydrogen Bonding in Organometallic Crystals. 6. X−H┄M Hydrogen Bonds and M┄(H−X) Pseudo-Agostic Bonds". <i>Organometallics</i>. <b>16</b> (9): 1846–1856. <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%2Fom9608364">10.1021/om9608364</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organometallics&rft.atitle=Hydrogen+Bonding+in+Organometallic+Crystals.+6.+X%E2%88%92H%E2%94%84M+Hydrogen+Bonds+and+M%E2%94%84%28H%E2%88%92X%29+Pseudo-Agostic+Bonds&rft.volume=16&rft.issue=9&rft.pages=1846-1856&rft.date=1997&rft_id=info%3Adoi%2F10.1021%2Fom9608364&rft.aulast=Braga&rft.aufirst=D.&rft.au=Grepioni%2C+F.&rft.au=Tedesco%2C+E.&rft.au=Biradha%2C+K.&rft.au=Desiraju%2C+G.+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAgostic+interaction" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Agostic_interaction&action=edit&section=8" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.ilpi.com/organomet/agostic.html">Agostic interactions</a></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 dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist 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.navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Organometallic_chemistry" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Organometallics" title="Template:Organometallics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Organometallics" title="Template talk:Organometallics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Organometallics" title="Special:EditPage/Template:Organometallics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Organometallic_chemistry" style="font-size:114%;margin:0 4em"><a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">Organometallic chemistry</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Principles</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/Crystal_field_theory" title="Crystal field theory">Crystal field theory</a></li> <li><a href="/wiki/Ligand_field_theory" 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 href="/wiki/Hapticity" title="Hapticity">Hapticity</a></li> <li><a href="/wiki/Spin_states_(d_electrons)" title="Spin states (d electrons)">spin states</a></li> <li><a class="mw-selflink selflink">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" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Organometallic_chemistry" title="Category:Organometallic chemistry">Category</a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Commons page"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span> <b><a href="https://commons.wikimedia.org/wiki/Category:Organometallic_chemistry" class="extiw" title="commons:Category:Organometallic chemistry">Commons</a></b></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Chemical_bonds" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="3"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Chemical_bonds" title="Template:Chemical bonds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemical_bonds" title="Template talk:Chemical bonds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemical_bonds" title="Special:EditPage/Template:Chemical bonds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Chemical_bonds" style="font-size:114%;margin:0 4em"><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bonds</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intramolecular_force" title="Intramolecular force">Intramolecular</a><br />(strong)</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/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 class="mw-selflink selflink">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 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 src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" 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