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<div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Doubly bridging carbide ligands</span> </div> </a> <ul id="toc-Doubly_bridging_carbide_ligands-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Terminal_carbides" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Terminal_carbides"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Terminal carbides</span> </div> </a> <ul id="toc-Terminal_carbides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Preparative_routes_and_characterization" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Preparative_routes_and_characterization"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Preparative routes and characterization</span> </div> </a> <button aria-controls="toc-Preparative_routes_and_characterization-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 Preparative routes and characterization subsection</span> </button> <ul id="toc-Preparative_routes_and_characterization-sublist" class="vector-toc-list"> <li id="toc-Carbido_clusters_2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carbido_clusters_2"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Carbido clusters</span> </div> </a> <ul id="toc-Carbido_clusters_2-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Doubly_bridging_carbide_ligands_2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Doubly_bridging_carbide_ligands_2"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Doubly bridging carbide ligands</span> </div> </a> <ul id="toc-Doubly_bridging_carbide_ligands_2-sublist" class="vector-toc-list"> <li id="toc-Cumulenic" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cumulenic"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.1</span> <span>Cumulenic</span> </div> </a> <ul id="toc-Cumulenic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metallocarbyne" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Metallocarbyne"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.2</span> <span>Metallocarbyne</span> </div> </a> <ul id="toc-Metallocarbyne-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Polar_covalent" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Polar_covalent"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.3</span> <span>Polar covalent</span> </div> </a> <ul id="toc-Polar_covalent-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Terminal_carbido_ligands" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Terminal_carbido_ligands"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Terminal carbido ligands</span> </div> </a> <ul id="toc-Terminal_carbido_ligands-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>See also</span> </div> </a> <ul id="toc-See_also-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> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> 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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">Coordination complex that contains a carbon atom as a ligand</div> <p>A <b>metal carbido complex</b> is a <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complex</a> that contains a <a href="/wiki/Carbon" title="Carbon">carbon</a> atom as a <a href="/wiki/Ligand" title="Ligand">ligand</a>. They are analogous to <a href="/wiki/Metal_nitrido_complex" title="Metal nitrido complex">metal nitrido complexes</a>. Carbido complexes are a molecular subclass of <a href="/wiki/Carbide" title="Carbide">carbides</a>, which are prevalent in organometallic and inorganic chemistry. Carbido complexes represent models for intermediates in <a href="/wiki/Fischer%E2%80%93Tropsch" class="mw-redirect" title="Fischer–Tropsch">Fischer–Tropsch</a> synthesis, <a href="/wiki/Olefin_metathesis" title="Olefin metathesis">olefin metathesis</a>, and related catalytic industrial processes.<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> Ruthenium-based carbido complexes are by far the most synthesized and characterized to date. Although, complexes containing chromium, gold, iron, nickel, molybdenum, osmium, rhenium, and tungsten cores are also known. Mixed-metal carbides are also known.<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><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> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Carbido_clusters">Carbido clusters</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metal_carbido_complex&action=edit&section=1" title="Edit section: Carbido clusters"><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:Fe5C(CO)15.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Fe5C%28CO%2915.png/220px-Fe5C%28CO%2915.png" decoding="async" width="220" height="215" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Fe5C%28CO%2915.png/330px-Fe5C%28CO%2915.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Fe5C%28CO%2915.png/440px-Fe5C%28CO%2915.png 2x" data-file-width="643" data-file-height="628" /></a><figcaption>Structure of <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap"><a href="/wiki/Iron" title="Iron">Fe</a><sub class="template-chem2-sub">5</sub>C(CO)<sub class="template-chem2-sub">15</sub></span>.<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></figcaption></figure> <p>Most molecular carbido complexes are clusters, usually featuring carbide as a six-fold <a href="/wiki/Bridging_ligand" title="Bridging ligand">bridging ligand</a>. Examples include [<a href="/wiki/Rhodium" title="Rhodium">Rh</a><sub>6</sub>C(CO)<sub>15</sub>]<sup>2−</sup>, and [<a href="/wiki/Ruthenium" title="Ruthenium">Ru</a><sub>6</sub>C(CO)<sub>16</sub>]<sup>2−</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> Though exceptions exist, such as the nonanuclear Ruthenium cluster (μ-C)Ru<sub>9</sub>(CO)<sub>14</sub> (μ<sup>3</sup>-η<sup>5</sup>: η<sup>2</sup>:η<sup>2</sup>-C<sub>9</sub>H<sub>7</sub>)<sub>2,</sub> containing a tripped trigonal prism geometry around the carbide.<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> </p><p>The <a href="/wiki/Iron" title="Iron">iron</a> carbonyl carbides exist not only in the encapsulated carbon ([<a href="/wiki/Iron" title="Iron">Fe</a><sub>6</sub>C(CO)<sub>16</sub>]<sup>2−</sup>) but also with exposed carbon centres as in Fe<sub>5</sub>C(CO)<sub>15</sub> and Fe<sub>4</sub>C(CO)<sub>13.</sub><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> </p><p> Bimetallic and exotic clusters such as metal carbide clusterfullerenes (MCCF's) have also been able to be prepared.<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><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><figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Au6C(PPh3)6.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Au6C%28PPh3%296.png/240px-Au6C%28PPh3%296.png" decoding="async" width="240" height="209" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Au6C%28PPh3%296.png/360px-Au6C%28PPh3%296.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Au6C%28PPh3%296.png/480px-Au6C%28PPh3%296.png 2x" data-file-width="862" data-file-height="749" /></a><figcaption>The complex <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Gold" title="Gold">Au</a><sub class="template-chem2-sub">6</sub>C(<a href="/wiki/Phosphorus" title="Phosphorus">P</a><a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">Ph</a><sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">6</sub>]<sup>2+</sup></span>, containing a carbon-gold core.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Doubly_bridging_carbide_ligands">Doubly bridging carbide ligands</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metal_carbido_complex&action=edit&section=2" title="Edit section: Doubly bridging carbide ligands"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Bridging carbido ligands can be subdivided into three classes: </p> <ul><li>cumulenic <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">L<sub class="template-chem2-sub"><i>n</i></sub>M=C=M'L<sub class="template-chem2-sub"><i>n</i></sub></span>,</li> <li>metallocarbyne <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">L<sub class="template-chem2-sub"><i>n</i></sub>M≡C−M'L<sub class="template-chem2-sub"><i>n</i></sub></span>, and</li> <li>polar covalent <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">L<sub class="template-chem2-sub"><i>n</i></sub>M≡C:→M'L<sub class="template-chem2-sub"><i>n</i></sub></span>.<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></ul> <p>Cumulenic compounds generally bridge two metal atoms of the same element and are symmetrical.<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> However, there are exceptions to this.<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> </p><p>In contrast, metallocarbyne compounds are generally constitutionally heterobimetallic, with complexes containing varying coordination geometries being common. These moieties have been able to serve as precursors to elaborate molecular scaffolds such as porphyrin derivatives.<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><p>The polar covalent class is distinguished from metallocarbynes by a very fine line. This carbide-metal interaction is considered labile in nature. Carbon here can be understood fundamentally as being similar to CO ligands, that is, dative (L-type). Although, this class has also been described to some extent being analogous to the behavior of Lewis acid adduct-forming terminal nitrido and oxo complexes e.g. (PMe<sub>2</sub>Ph)<sub>2</sub>Cl-Re≡N-BCl<sub>3</sub> and tBu(CH<sub>2</sub>)<sub>3</sub>(Br)W=O-AlBr<sub>3</sub>.<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> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:PolarCovalent.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/PolarCovalent.png/220px-PolarCovalent.png" decoding="async" width="220" height="153" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/9/9b/PolarCovalent.png 1.5x" data-file-width="228" data-file-height="159" /></a><figcaption>Zwitterionic canonical depiction of polar covalent metal-carbide bond</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Terminal_carbides">Terminal carbides</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metal_carbido_complex&action=edit&section=3" title="Edit section: Terminal carbides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In rare cases, carbido ligands are terminal. One example is <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RuC(PCy<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>Cl<sub class="template-chem2-sub">2</sub></span> with a Ru-C distance of 163 <a href="/wiki/Picometre" title="Picometre">pm</a>, typical for a triple bond.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The complex can be obtained by metathesis of <a href="/wiki/Vinyl_acetate" title="Vinyl acetate">vinyl acetate</a> to give <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Ru(CH-<i>p</i>-C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">4</sub>Me)(PCy<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>Cl<sub class="template-chem2-sub">2</sub>]</span> results in a metastable <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ru(Cl<sub class="template-chem2-sub">2</sub>)(PCy<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub>HOAc</span> complex, which eliminates acetic acid.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Such transition metal, one coordinate-carbon bonded complexes are comparable to carbon monoxide, cyanide, and isonitrile analogues. These carbides can be used as synthons to access a wide range of carbyne complexes, the most notable being Fischer carbynes.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> American chemist <a href="/wiki/Christopher_C._Cummins" title="Christopher C. Cummins">Christopher C. Cummins</a> is one of the pioneers of this area. </p> <div class="mw-heading mw-heading2"><h2 id="Preparative_routes_and_characterization">Preparative routes and characterization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metal_carbido_complex&action=edit&section=4" title="Edit section: Preparative routes and characterization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Carbido_clusters_2">Carbido clusters</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metal_carbido_complex&action=edit&section=5" title="Edit section: Carbido clusters"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Synthesis of carbido clusters can be accomplished by hydrolysis, thermolysis of labile ligands, thermal rearrangements, and photolysis. Their synthesis has historically been crudely achieved by serendipitous chance following apparent random molecular organization. One example is the following reaction: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:CarbidoClusterSynthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/CarbidoClusterSynthesis.png/343px-CarbidoClusterSynthesis.png" decoding="async" width="343" height="53" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/CarbidoClusterSynthesis.png/515px-CarbidoClusterSynthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9a/CarbidoClusterSynthesis.png/686px-CarbidoClusterSynthesis.png 2x" data-file-width="713" data-file-height="110" /></a></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Doubly_bridging_carbide_ligands_2">Doubly bridging carbide ligands</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metal_carbido_complex&action=edit&section=6" title="Edit section: Doubly bridging carbide ligands"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Cumulenic">Cumulenic</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metal_carbido_complex&action=edit&section=7" title="Edit section: Cumulenic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Synthetic routes to cumulenic carbido complexes can be efficient and lead to rapid, near quantitative product formation with simple purifications.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> This dimerization involves the formation of a vinylidene from an alkyne. Mechanistically, there are various proposed pathways, starting with oxidative addition of the alkyne to the metal core, followed by either intramolecular 1,2-H shifts or intermolecular 1,3-H shifts.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> For Ruthenium coordination complexes, bridging Ru-Cl bond lengths have been observed to lie in the range of 1.76-1.8 Å. Ru-C bonds can vary significantly as a result of trans effect phenomena which is caused by the respective ethylene and vinylidene ligands. </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Synthesis_of_Cumulenic_Complex.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Synthesis_of_Cumulenic_Complex.png/264px-Synthesis_of_Cumulenic_Complex.png" decoding="async" width="264" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Synthesis_of_Cumulenic_Complex.png/396px-Synthesis_of_Cumulenic_Complex.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Synthesis_of_Cumulenic_Complex.png/528px-Synthesis_of_Cumulenic_Complex.png 2x" data-file-width="962" data-file-height="381" /></a><figcaption>Acetylene-based synthesis of cumulenic carbido complex</figcaption></figure> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Alkynetovinylidene.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Alkynetovinylidene.png/305px-Alkynetovinylidene.png" decoding="async" width="305" height="195" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Alkynetovinylidene.png/458px-Alkynetovinylidene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/69/Alkynetovinylidene.png/610px-Alkynetovinylidene.png 2x" data-file-width="700" data-file-height="447" /></a><figcaption>Proposed hydride shift mechanisms for alkyne being transformed into vinylidene</figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Metallocarbyne">Metallocarbyne</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metal_carbido_complex&action=edit&section=8" title="Edit section: Metallocarbyne"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The appropriate halocarbyne precursors of choice can be reacted with <a href="/wiki/Organolithium_reagent" title="Organolithium reagent">organolithium reagents</a> to afford the respective lithiocarbyne derivate by virtue of <a href="/wiki/Metal%E2%80%93halogen_exchange" title="Metal–halogen exchange">lithium/halogen exchange</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> This species can serve as a lynchpin for subsequent carbide linkage with an additional metal complex. Phosphine-based analogues were first introduced by Templeton and co.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> These types of complexes can be characterized crystallographically and are distinguishable by their C<sub>s</sub> symmetry. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Phosphoniocarbyne.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Phosphoniocarbyne.png/220px-Phosphoniocarbyne.png" decoding="async" width="220" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Phosphoniocarbyne.png/330px-Phosphoniocarbyne.png 1.5x, //upload.wikimedia.org/wikipedia/commons/2/28/Phosphoniocarbyne.png 2x" data-file-width="428" data-file-height="134" /></a><figcaption>Synthesis of Templeton Phosphoniocarbyne</figcaption></figure> <figure class="mw-halign-none" typeof="mw:File/Thumb"><a href="/wiki/File:Bridging_Carbido_Complex.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Bridging_Carbido_Complex.png/257px-Bridging_Carbido_Complex.png" decoding="async" width="257" height="181" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Bridging_Carbido_Complex.png/386px-Bridging_Carbido_Complex.png 1.5x, //upload.wikimedia.org/wikipedia/commons/d/d9/Bridging_Carbido_Complex.png 2x" data-file-width="454" data-file-height="319" /></a><figcaption>Common synthetic route for bridging carbido complex</figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Polar_covalent">Polar covalent</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metal_carbido_complex&action=edit&section=9" title="Edit section: Polar covalent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Addition of tricyclohexylphosphine to the carbene complex (PPh<sub>3</sub>)<sub>2</sub>(Cl)<sub>2</sub>Ru=C(CHCO<sub>2</sub>Me)<sub>2</sub> results in olefin extrusion and yields an air stable anionic carbido complex. This species displaces a dimethyl sulfide ligand from PdCl<sub>2</sub>(SMe)<sub>2</sub> to give the μ-carbido bimetallic complex (PCy<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub>Ru≡C-PdCl<sub>2</sub>(SMe<sub>2</sub>). Spark towards a novel type of bonding was proposed following empirical observations wherein the carbido-palladium interaction could be readily disturbed. Reversible coordination ensues upon exposure of the bimetallic complex to carbon monoxide. Additionally, no coordination occurs if the anionic carbido complex contains bulky ligands such as <a href="/wiki/SIMes" title="SIMes">H<sub>2</sub>IMes</a>. This indicates that the thermodynamic sink towards making the C-M bond is not very favorable, suggesting a weak interaction. Although not intuitive, characterization of this type of bonding can be inferred if <sup>13</sup>C NMR shifts are observed to be far downfield, and C-M bond lengths are similar to those of complexes proven to contain carbon-based σ-donor ligands such as [(Et<sub>2</sub>H<sub>2</sub>Im)PdCl(μ-Cl)]<sub>2.</sub><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:PolarCovalentSynthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/PolarCovalentSynthesis.png/610px-PolarCovalentSynthesis.png" decoding="async" width="610" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/PolarCovalentSynthesis.png/915px-PolarCovalentSynthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/3/3f/PolarCovalentSynthesis.png 2x" data-file-width="1078" data-file-height="199" /></a><figcaption>Preparation of carbide complex exhibiting polar covalent C-M bonding</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Terminal_carbido_ligands">Terminal carbido ligands</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metal_carbido_complex&action=edit&section=10" title="Edit section: Terminal carbido ligands"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metathesis using Grubbs-type alkylidene complexes can be used to synthesize terminal carbido-containing complexes. One example is RuC(PCy<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub> with a Ru-C distance of 163 <a href="/wiki/Picometre" title="Picometre">pm</a>, typical for a triple bond.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> The complex can be obtained by metathesis of <a href="/wiki/Vinyl_acetate" title="Vinyl acetate">vinyl acetate</a> to give [Ru(CH-<i>p</i>-C<sub>6</sub>H<sub>4</sub>Me)(PCy<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub>] results in a metastable Ru(Cl<sub>2</sub>)(PCy<sub>3</sub>)<sub>2</sub>C<sub>2</sub>HOAc complex, which eliminates acetic acid.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>The "naked" carbido ligand is weakly basic, forming complexes with other metal centers. The C-M bond is typically found to be around 1.65 <a href="/wiki/Angstroms" class="mw-redirect" title="Angstroms">Å</a>. The <sup>13</sup><a href="/wiki/CNMR" class="mw-redirect" title="CNMR">C NMR</a> resonance values for the carbido carbons vary widely, but range from δ211-406.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Another example of a terminal carbido complex is Li[MoC(NR2)3] (Mo-C distance of 172 pm), which forms upon deprotonation of the respective methylidyne precursor.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Carbenesynthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Carbenesynthesis.png/680px-Carbenesynthesis.png" decoding="async" width="680" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Carbenesynthesis.png/1020px-Carbenesynthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Carbenesynthesis.png/1360px-Carbenesynthesis.png 2x" data-file-width="2044" data-file-height="433" /></a><figcaption>Synthesis of a terminal carbido complex.</figcaption></figure> <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=Metal_carbido_complex&action=edit&section=11" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Metallocarbohedryne" title="Metallocarbohedryne">Metallocarbohedryne</a> ("met-car"), a stable cluster with formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">M<sub class="template-chem2-sub">8</sub>C<sub class="template-chem2-sub">12</sub></span> (M = Ti, Zr, V, etc.<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Avoid_weasel_words" class="mw-redirect" title="Wikipedia:Avoid weasel words"><span title="The material near this tag possibly uses too vague attribution or weasel words. (September 2022)">which?</span></a></i>]</sup>)</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=Metal_carbido_complex&action=edit&section=12" 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"><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="CITEREFReinholdtBendix2022" class="citation journal cs1">Reinholdt, Anders; 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.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 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 class="mw-selflink selflink">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="Coordination_complexes" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed 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"><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:Coordination_complexes" title="Template:Coordination complexes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Coordination_complexes" title="Template talk:Coordination complexes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Coordination_complexes" title="Special:EditPage/Template:Coordination complexes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Coordination_complexes" style="font-size:114%;margin:0 4em"><a href="/wiki/Coordination_complex" title="Coordination complex">Coordination complexes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">H donors:</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/Transition_metal_hydride" title="Transition metal hydride">H<sup>−</sup></a></li> <li><a href="/wiki/Dihydrogen_complex" title="Dihydrogen complex">H<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">B donors:</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/Transition_metal_boryl_complex" title="Transition metal boryl complex">BR<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Metallaborane" title="Metallaborane">B<sub>m</sub>H<sub>n</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">C donors:</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/Transition_metal_alkyl_complexes" title="Transition metal alkyl complexes">R<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_acyl_complexes" title="Transition metal acyl complexes">RC(O)<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_formyl_complex" title="Transition metal formyl complex">HC(O)<sup>−</sup></a></li> <li><a href="/wiki/Transition-metal_allyl_complex" title="Transition-metal allyl complex">CH<sub>2</sub>＝CH-CH<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Trimethylenemethane_complexes" title="Trimethylenemethane complexes">C(CH<sub>2</sub>)<sub>3</sub></a></li> <li><a href="/wiki/Transition_metal_alkene_complex" title="Transition metal alkene complex">CH<sub>2</sub>＝CH<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_alkyne_complex" title="Transition metal alkyne complex">RC<sub>2</sub>R</a></li> <li><a href="/wiki/Transition_metal_benzyne_complex" title="Transition metal benzyne complex">C<sub>6</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Cyanometalate" title="Cyanometalate">CN<sup>−</sup></a></li> <li><a href="/wiki/Metal_carbonyl" title="Metal carbonyl">CO</a></li> <li><a href="/wiki/Metal_carbon_dioxide_complex" title="Metal carbon dioxide complex">CO<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_carbide" class="mw-redirect" title="Transition metal carbide">C<sup>4-</sup></a></li> <li><a href="/wiki/Transition_metal_arene_complex" title="Transition metal arene complex">C<sub>6</sub>R<sub>6</sub></a></li> <li><a href="/wiki/Transition_metal_fullerene_complex" title="Transition metal fullerene complex">C<sub>60</sub> & C<sub>70</sub></a></li> <li><a href="/wiki/Transition_metal_isocyanide_complexes" title="Transition metal isocyanide complexes">RNC</a></li> <li><a href="/wiki/Transition_metal_carbene_complex" title="Transition metal carbene complex">=CR<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_carbyne_complex" title="Transition metal carbyne complex">≡CR</a></li> <li><a href="/wiki/Metallocene" title="Metallocene">C<sub>5</sub>H<sub>5</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_indenyl_complex" title="Transition metal indenyl complex">C<sub>9</sub>H<sub>7</sub><sup>−</sup></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Si donors:</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/Transition_metal_silane_complexes" class="mw-redirect" title="Transition metal silane complexes">H<sub>n</sub>SiR<sub>4−n</sub></a></li> <li><a href="/wiki/Transition_metal_silyl_complexes" title="Transition metal silyl complexes">R<sub>3</sub>Si<sup>−</sup></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">N donors:</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/Metal_ammine_complex" title="Metal ammine complex">NH<sub>3</sub></a></li> <li><a href="/wiki/Transition_metal_azide_complex" title="Transition metal azide complex">N<sub>3</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_imidazole_complex" title="Transition metal imidazole complex">imidazole</a></li> <li><a href="/wiki/Metal_nitrosyl_complex" title="Metal nitrosyl complex">NO</a></li> <li><a href="/wiki/Transition_metal_nitroso_complexes" title="Transition metal nitroso complexes">RNO</a></li> <li><a href="/wiki/Transition_metal_nitrite_complex#Bonding_modes" title="Transition metal nitrite complex">NO<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_pyridine_complexes" title="Transition metal pyridine complexes">py</a></li> <li><a href="/wiki/Transition_metal_amino_acid_complexes" title="Transition metal amino acid complexes">amino acid</a></li> <li><a href="/wiki/Metal_nitrido_complex" title="Metal nitrido complex">N<sup>3-</sup></a></li> <li><a href="/wiki/Transition_metal_imido_complex" title="Transition metal imido complex">RN<sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_nitrile_complexes" title="Transition metal nitrile complexes">RCN</a></li> <li><a href="/wiki/Transition_metal_complexes_of_2,2%27-bipyridine" title="Transition metal complexes of 2,2'-bipyridine">bipy</a></li> <li><a href="/wiki/Transition_metal_complexes_of_1,10-phenanthroline" title="Transition metal complexes of 1,10-phenanthroline">phen</a></li> <li><a href="/wiki/Transition_metal_porphyrin_complexes" title="Transition metal porphyrin complexes">porphyrin</a></li> <li><a href="/wiki/Metal_bis(trimethylsilyl)amides" title="Metal bis(trimethylsilyl)amides">(Me<sub>3</sub>Si)<sub>2</sub>N<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_dinitrogen_complex" title="Transition metal dinitrogen complex">N<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_complexes_of_thiocyanate" title="Transition metal complexes of thiocyanate"><i>N</i>CS<sup>-</sup></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">P donors:</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/Metal_phosphine_complex" class="mw-redirect" title="Metal phosphine complex">PR<sub>3</sub></a></li> <li><a href="/wiki/Transition_metal_phosphido_complexes" title="Transition metal phosphido complexes">PR<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_complexes_of_phosphine_oxides#Secondary_phosphine_oxides_as_ligands" title="Transition metal complexes of phosphine oxides">PR<sub>2</sub>OH</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">O donors:</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/Metal_aquo_complex" title="Metal aquo complex">H<sub>2</sub>O</a></li> <li><a href="/wiki/Transition_metal_ether_complex" title="Transition metal ether complex">R<sub>2</sub>O</a></li> <li><a href="/wiki/Metal_alkoxide" class="mw-redirect" title="Metal alkoxide">RO<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_oxo_complex" title="Transition metal oxo complex">O<sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_dioxygen_complex" title="Transition metal dioxygen complex">O<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_carbonate_and_bicarbonate_complexes" title="Transition metal carbonate and bicarbonate complexes">CO<sub>3</sub><sup>2-</sup>/HCO<sub>3</sub><sup>-</sup></a></li> <li><a href="/wiki/Transition_metal_oxalate_complex" title="Transition metal oxalate complex">C<sub>2</sub>O<sub>4</sub><sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_carboxylate_complex" title="Transition metal carboxylate complex">RCO<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Metal_acetylacetonates" title="Metal acetylacetonates">acac</a></li> <li><a href="/wiki/Transition_metal_complexes_of_aldehydes_and_ketones" title="Transition metal complexes of aldehydes and ketones">R<sub>2</sub>CO</a></li> <li><a href="/wiki/Transition_metal_nitrite_complex" title="Transition metal nitrite complex">ONO<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_nitrate_complex" title="Transition metal nitrate complex">NO<sub>3</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_perchlorate_complexes" title="Transition metal perchlorate complexes">ClO<sub>4</sub><sup>-</sup></a></li> <li><a href="/wiki/Transition_metal_complexes_of_pyridine-N-oxides" title="Transition metal complexes of pyridine-N-oxides">C<sub>5</sub>H<sub>5</sub>NO</a></li> <li><a href="/wiki/Transition_metal_sulfoxide_complex" title="Transition metal sulfoxide complex">OSR<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_sulfate_complex" title="Transition metal sulfate complex">SO<sub>4</sub><sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_phosphate_complex" title="Transition metal phosphate complex">PO<sub>4</sub><sup>3-</sup></a></li> <li><a href="/wiki/Transition_metal_complexes_of_phosphine_oxides" title="Transition metal complexes of phosphine oxides">OPR<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">S donors:</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/Transition_metal_dithiocarbamate_complexes" title="Transition metal dithiocarbamate complexes">R<sub>2</sub>NCS<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_thiolate_complex" title="Transition metal thiolate complex">RS<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_thioether_complex" title="Transition metal thioether complex">R<sub>2</sub>S</a></li> <li><a href="/wiki/Metal_dithiolene_complex" title="Metal dithiolene complex">R<sub>2</sub>C<sub>2</sub>S<sub>2</sub><sup>2-</sup></a></li> <li><a href="/wiki/Metal_sulfur_dioxide_complex" title="Metal sulfur dioxide complex">SO<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_thiosulfate_complex" title="Transition metal thiosulfate complex">S<sub>2</sub>O<sub>3</sub><sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_sulfoxide_complex" title="Transition metal sulfoxide complex">SR<sub>2</sub>O</a></li> <li><a href="/wiki/Transition_metal_complexes_of_thiocyanate" title="Transition metal complexes of thiocyanate">NC<i>S</i><sup>-</sup></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Halide donors:</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="/w/index.php?title=Fluoro_complex&action=edit&redlink=1" class="new" title="Fluoro complex (page does not exist)">F<sup>−</sup></a></li> <li><a href="/wiki/Difluorine_complex" title="Difluorine complex">F<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_chloride_complex" title="Transition metal chloride complex">Cl<sup>−</sup></a></li> <li><a href="/w/index.php?title=Bromo_complex&action=edit&redlink=1" class="new" title="Bromo complex (page does not exist)">Br<sup>−</sup></a></li> <li><a href="/w/index.php?title=Iodo_complex&action=edit&redlink=1" class="new" title="Iodo complex (page does not exist)">I<sup>−</sup></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" href="https://en.wikipedia.org/w/index.php?title=Metal_carbido_complex&oldid=1184679693">https://en.wikipedia.org/w/index.php?title=Metal_carbido_complex&oldid=1184679693</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Organometallic_compounds" title="Category:Organometallic compounds">Organometallic compounds</a></li><li><a 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