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Three-center two-electron bond - Wikipedia

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href="https://fa.wikipedia.org/wiki/%D9%BE%DB%8C%D9%88%D9%86%D8%AF_%D8%AF%D9%88_%D8%A7%D9%84%DA%A9%D8%AA%D8%B1%D9%88%D9%86_-%D8%B3%D9%87_%D9%85%D8%B1%DA%A9%D8%B2%DB%8C" title="پیوند دو الکترون -سه مرکزی – Persian" lang="fa" hreflang="fa" data-title="پیوند دو الکترون -سه مرکزی" 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/Liaison_%C3%A0_trois_centres_et_deux_%C3%A9lectrons" title="Liaison à trois centres et deux électrons – French" lang="fr" hreflang="fr" data-title="Liaison à trois centres et deux électrons" 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/Ikatan_tiga-pusat_dua-elektron" title="Ikatan tiga-pusat dua-elektron – 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</div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Electron-deficient chemical bond where three atoms share two electrons</div> <p class="mw-empty-elt"> </p><p>A <b>three-center two-electron (3c–2e) bond</b> is an <a href="/wiki/Electron_deficiency" title="Electron deficiency">electron-deficient</a> <a href="/wiki/Chemical_bond" title="Chemical bond">chemical bond</a> where three <a href="/wiki/Atom" title="Atom">atoms</a> share two <a href="/wiki/Electron" title="Electron">electrons</a>. The combination of three <a href="/wiki/Atomic_orbital" title="Atomic orbital">atomic orbitals</a> form three <a href="/wiki/Molecular_orbital" title="Molecular orbital">molecular orbitals</a>: one bonding, one <i>non</i>-bonding, and one <i>anti</i>-bonding. The two electrons go into the bonding orbital, resulting in a net bonding effect and constituting a chemical bond among all three atoms. In many common bonds of this type, the bonding orbital is shifted towards two of the three atoms instead of being spread equally among all three. Example molecules with 3c–2e bonds are the <a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">trihydrogen cation</a> (<span class="chemf nowrap">H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>) and <a href="/wiki/Diborane" title="Diborane">diborane</a> (<span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span></span>). In these two structures, the three atoms in each 3c-2e bond form an angular geometry, leading to a <a href="/wiki/Bent_bond" title="Bent bond">bent bond</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Boranes_and_carboranes">Boranes and carboranes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Three-center_two-electron_bond&amp;action=edit&amp;section=1" title="Edit section: Boranes and carboranes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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">Further information: <a href="/wiki/Polyhedral_skeletal_electron_pair_theory" title="Polyhedral skeletal electron pair theory">Polyhedral skeletal electron pair theory</a></div> <p>An extended version of the 3c–2e bond model features heavily in <a href="/wiki/Cluster_compound" class="mw-redirect" title="Cluster compound">cluster compounds</a> described by the polyhedral skeletal electron pair theory, such as <a href="/wiki/Boranes" title="Boranes">boranes</a> and <a href="/wiki/Carborane" title="Carborane">carboranes</a>. These molecules derive their stability from having a completely filled set of bonding molecular orbitals as outlined by <a href="/wiki/Polyhedral_skeletal_electron_pair_theory" title="Polyhedral skeletal electron pair theory">Wade's rules</a>. </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Diborane_resonance.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Diborane_resonance.svg/400px-Diborane_resonance.svg.png" decoding="async" width="400" height="49" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Diborane_resonance.svg/600px-Diborane_resonance.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/80/Diborane_resonance.svg/800px-Diborane_resonance.svg.png 2x" data-file-width="570" data-file-height="70" /></a><figcaption>Resonance structures of 3c-2e bond in diborane.</figcaption></figure> <p>The monomer <a href="/wiki/Borane" title="Borane">BH<sub>3</sub></a> is unstable since the boron atom has an empty p-orbital. A <b>B−H−B</b> 3-center-2-electron bond is formed when a boron atom shares electrons with a B−H bond on another boron atom. The two electrons (corresponding to one bond) in a <b>B−H−B</b> bonding molecular orbital are spread out across three internuclear spaces.<sup id="cite_ref-Mayer_1-0" class="reference"><a href="#cite_note-Mayer-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> </p><p>In <a href="/wiki/Diborane" title="Diborane">diborane</a> (B<sub>2</sub>H<sub>6</sub>), there are two such 3c-2e bonds: two H atoms bridge the two B atoms, leaving two additional H atoms in ordinary B−H bonds on each B. As a result, the molecule achieves stability since each B participates in a total of four bonds and all bonding molecular orbitals are filled, although two of the four bonds are 3-center B−H−B bonds. The reported <a href="/wiki/Bond_order" title="Bond order">bond order</a> for each B−H interaction in a bridge is 0.5,<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> so that the bridging B−H−B bonds are weaker and longer than the terminal B−H bonds, as shown by the <a href="/wiki/Bond_length" title="Bond length">bond lengths</a> in the structural diagram. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Diborane-2D.png" class="mw-file-description" title="Diborane. The two central hydrogen atoms are simultaneously bonded to both boron atoms in 3c-2e bonds."><img alt="Diborane. The two central hydrogen atoms are simultaneously bonded to both boron atoms in 3c-2e bonds." src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Diborane-2D.png/280px-Diborane-2D.png" decoding="async" width="280" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Diborane-2D.png/420px-Diborane-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/Diborane-2D.png/560px-Diborane-2D.png 2x" data-file-width="1100" data-file-height="526" /></a></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Transition_metal_complexes">Transition metal complexes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Three-center_two-electron_bond&amp;action=edit&amp;section=2" title="Edit section: Transition metal complexes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure 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/144px-Cp%27Mn%28CO%292%28HSiPh3%29.png" decoding="async" width="144" height="132" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Cp%27Mn%28CO%292%28HSiPh3%29.png/216px-Cp%27Mn%28CO%292%28HSiPh3%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Cp%27Mn%28CO%292%28HSiPh3%29.png/288px-Cp%27Mn%28CO%292%28HSiPh3%29.png 2x" data-file-width="468" data-file-height="429" /></a><figcaption>One of many <a href="/wiki/Transition_metal_silane_complexes" class="mw-redirect" title="Transition metal silane complexes">transition metal silane complexes</a>, examples feature three-center two-electron bonding.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup></figcaption></figure> <p>Three-center, two-electron bonding is pervasive in organotransition metal chemistry. A celebrated family of compounds featuring such interactions as called <a href="/wiki/Agostic_complex" class="mw-redirect" title="Agostic complex">agostic complexes</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Other_compounds">Other compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Three-center_two-electron_bond&amp;action=edit&amp;section=3" title="Edit section: Other compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>This bonding pattern is also seen in <a href="/wiki/Trimethylaluminium" title="Trimethylaluminium">trimethylaluminium</a>, which forms a dimer Al<sub>2</sub>(CH<sub>3</sub>)<sub>6</sub> with the carbon atoms of two of the <a href="/wiki/Methyl_group" title="Methyl group">methyl groups</a> in bridging positions. This type of bond also occurs in <a href="/wiki/Carbon" title="Carbon">carbon</a> compounds, where it is sometimes referred to as <a href="/wiki/Hyperconjugation" title="Hyperconjugation">hyperconjugation</a>; another name for asymmetrical three-center two-electron bonds. </p> <div class="mw-heading mw-heading3"><h3 id="Beryllium">Beryllium</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Three-center_two-electron_bond&amp;action=edit&amp;section=4" title="Edit section: Beryllium"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first stable subvalent Be complex ever observed contains a three-center two-electron π-bond that consists of donor-acceptor interactions over the C-Be-C core of a Be(0)-carbene adduct.<sup id="cite_ref-Arrowsmith_4-0" class="reference"><a href="#cite_note-Arrowsmith-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Carbocations">Carbocations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Three-center_two-electron_bond&amp;action=edit&amp;section=5" title="Edit section: Carbocations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Carbocation" title="Carbocation">Carbocation</a> <a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">rearrangement reactions</a> occur through three-center bond transition states. Because the three center bond structures have about the same energy as carbocations, there is generally virtually no activation energy for these rearrangements so they occur with extraordinarily high rates. </p><p><a href="/wiki/Carbonium_ion" title="Carbonium ion">Carbonium ions</a> such as <a href="/wiki/Ethanium" title="Ethanium">ethanium</a> <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">7</sub></span></span></span> have three-center two-electron bonds. Perhaps the best known and studied structure of this sort is the <a href="/wiki/2-Norbornyl_cation" title="2-Norbornyl cation">2-Norbornyl cation</a>. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Three-center_two-electron_bond&amp;action=edit&amp;section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Three-center_four-electron_bond" title="Three-center four-electron bond">Three-center four-electron bond</a></li> <li><a href="/wiki/2-Norbornyl_cation" title="2-Norbornyl cation">2-Norbornyl cation</a></li> <li><a href="/wiki/Dihydrogen_complex" title="Dihydrogen complex">Dihydrogen complex</a></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=Three-center_two-electron_bond&amp;action=edit&amp;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"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-Mayer-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Mayer_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFI._Mayer1989" class="citation journal cs1">I. Mayer (1989). "Bond orders in three-centre bonds: an analytical investigation into the electronic structure of diborane and the three-centre four-electron bonds of hypervalent sulphur". <i><a href="/wiki/Journal_of_Molecular_Structure" title="Journal of Molecular Structure">Journal of Molecular Structure</a></i>. <b>186</b>: <span class="nowrap">43–</span>52. <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%2F0166-1280%2889%2987037-X">10.1016/0166-1280(89)87037-X</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+Molecular+Structure&amp;rft.atitle=Bond+orders+in+three-centre+bonds%3A+an+analytical+investigation+into+the+electronic+structure+of+diborane+and+the+three-centre+four-electron+bonds+of+hypervalent+sulphur&amp;rft.volume=186&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E43-%3C%2Fspan%3E52&amp;rft.date=1989&amp;rft_id=info%3Adoi%2F10.1016%2F0166-1280%2889%2987037-X&amp;rft.au=I.+Mayer&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AThree-center+two-electron+bond" class="Z3988"></span></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/F._Albert_Cotton" title="F. Albert Cotton">F. Albert Cotton</a>, <a href="/wiki/Geoffrey_Wilkinson" title="Geoffrey Wilkinson">Geoffrey Wilkinson</a> and Paul L. Gaus, <i>Basic Inorganic Chemistry</i>, 2nd ed. (Wiley 1987), p.113</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"><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>. <b>53</b>: <span class="nowrap">217–</span>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>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Adv.+Organomet.+Chem.&amp;rft.atitle=Recent+advances+in+nonclassical+interligand+SiH+interactions&amp;rft.volume=53&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E217-%3C%2Fspan%3E309&amp;rft.date=2005&amp;rft_id=info%3Adoi%2F10.1016%2Fs0065-3055%2805%2953006-5&amp;rft.au=Nikonov%2C+G.+I.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AThree-center+two-electron+bond" class="Z3988"></span></span> </li> <li id="cite_note-Arrowsmith-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-Arrowsmith_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFArrowsmith,_M;_Braunschweig,_H.;_Celik,_M.A.;_Dellermann,_T.;_Dewhurst,_R.D.;_Ewing,_W.C.;_Hammond,_K.;_Kramer,_T.;_Krummenacher,_I.;_Mies,_J.;_Radacki,_K.;_and_Schuster,_J.K.2016" class="citation journal cs1">Arrowsmith, M; Braunschweig, H.; Celik, M.A.; Dellermann, T.; Dewhurst, R.D.; Ewing, W.C.; Hammond, K.; Kramer, T.; Krummenacher, I.; Mies, J.; Radacki, K.; and Schuster, J.K. (2016). "Neutral zero-valent s-block complexes with strong multiple bonding". <i>Nature Chemistry</i>. <b>8</b> (9): <span class="nowrap">890–</span>894. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2016NatCh...8..890A">2016NatCh...8..890A</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnchem.2542">10.1038/nchem.2542</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27334631">27334631</a>.</cite><span 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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 class="mw-selflink selflink">3c–2e</a></li> <li><a href="/wiki/Four-center_two-electron_bond" title="Four-center two-electron bond">4c–2e</a></li> <li><a href="/wiki/Eight-center_two-electron_bond" class="mw-redirect" title="Eight-center two-electron bond">8c–2e</a></li></ul></li> <li><a href="/wiki/Hypervalent_molecule" title="Hypervalent molecule">Hypervalence</a> <ul><li><a href="/wiki/Three-center_four-electron_bond" title="Three-center four-electron bond">3c–4e</a></li></ul></li> <li><a href="/wiki/Agostic_interaction" title="Agostic interaction">Agostic</a></li> <li><a href="/wiki/Bent_bond" title="Bent bond">Bent</a></li> <li><a href="/wiki/Coordinate_covalent_bond" title="Coordinate covalent bond">Coordinate (dipolar)</a></li> <li><a href="/wiki/Pi_backbonding" title="Pi backbonding">Pi backbond</a></li> <li><a href="/wiki/Metal%E2%80%93ligand_multiple_bond" title="Metal–ligand multiple bond">Metal–ligand multiple bond</a></li> <li><a href="/wiki/Charge-shift_bond" title="Charge-shift bond">Charge-shift</a></li> <li><a href="/wiki/Hapticity" title="Hapticity">Hapticity</a></li> <li><a href="/wiki/Conjugated_system" title="Conjugated system">Conjugation</a></li> <li><a href="/wiki/Hyperconjugation" title="Hyperconjugation">Hyperconjugation</a></li> <li><a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a> <ul><li><a href="/wiki/Homoaromaticity" title="Homoaromaticity">homo</a></li> <li><a href="/wiki/Bicycloaromaticity" title="Bicycloaromaticity">bicyclo</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Metallic_bonding" title="Metallic bonding">Metallic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Metal_aromaticity" title="Metal aromaticity">Metal aromaticity</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ionic_bonding" title="Ionic bonding">Ionic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li class="mw-empty-elt"></li></ul> </div></td></tr></tbody></table><div></div></td><td class="noviewer navbox-image" rowspan="4" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/File:Ligatio-covalens.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/200px-Ligatio-covalens.svg.png" decoding="async" width="200" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/300px-Ligatio-covalens.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/400px-Ligatio-covalens.svg.png 2x" data-file-width="597" data-file-height="265" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Chemfm_carbon_monoxide_3_1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/200px-Chemfm_carbon_monoxide_3_1.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/300px-Chemfm_carbon_monoxide_3_1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/400px-Chemfm_carbon_monoxide_3_1.svg.png 2x" data-file-width="99" data-file-height="56" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Pi-Bond.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/200px-Pi-Bond.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/300px-Pi-Bond.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/400px-Pi-Bond.svg.png 2x" data-file-width="1920" data-file-height="1080" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intermolecular_force" title="Intermolecular force">Intermolecular</a><br />(weak)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Van_der_Waals_force" title="Van der Waals force">Van der Waals<br />forces</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/London_dispersion_force" title="London dispersion force">London dispersion</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_bond" title="Hydrogen bond">Hydrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Low-barrier_hydrogen_bond" title="Low-barrier hydrogen bond">Low-barrier</a></li> <li><a href="/wiki/Resonance-assisted_hydrogen_bond" class="mw-redirect" title="Resonance-assisted hydrogen bond">Resonance-assisted</a></li> <li><a href="/wiki/Symmetric_hydrogen_bond" title="Symmetric hydrogen bond">Symmetric</a></li> <li><a href="/wiki/Dihydrogen_bond" title="Dihydrogen bond">Dihydrogen bonds</a></li> <li><a href="/wiki/C%E2%80%93H%C2%B7%C2%B7%C2%B7O_interaction" title="C–H···O interaction">C–H···O interaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Non-covalent_interactions" class="mw-redirect" title="Non-covalent interactions">Noncovalent</a><br />other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mechanically_interlocked_molecular_architectures" title="Mechanically interlocked molecular architectures">Mechanical</a></li> <li><a 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&#39;s rule">Hückel's rule</a></li> <li><a href="/wiki/Baird%27s_rule" title="Baird&#39;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> <!-- NewPP limit report Parsed by mw‐web.codfw.main‐7777d9bc4f‐rd4vq Cached time: 20250204085401 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.271 seconds Real time usage: 0.354 seconds Preprocessor visited node count: 1347/1000000 Post‐expand include size: 51689/2097152 bytes Template argument size: 3074/2097152 bytes Highest expansion depth: 16/100 Expensive parser function count: 4/500 Unstrip recursion depth: 1/20 Unstrip post‐expand size: 21667/5000000 bytes Lua time usage: 0.172/10.000 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