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href="#η2,_η2-coordination_bridging_two_metal_centers"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>η<sup>2</sup>, η<sup>2</sup>-coordination bridging two metal centers</span> </div> </a> <ul id="toc-η2,_η2-coordination_bridging_two_metal_centers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Benzyne_complexes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Benzyne_complexes"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Benzyne complexes</span> </div> </a> <ul id="toc-Benzyne_complexes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Applications</span> </div> </a> <ul id="toc-Applications-sublist" class="vector-toc-list"> </ul> </li> <li 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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"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Semihydrogenation&redirect=no" class="mw-redirect" title="Semihydrogenation">Semihydrogenation</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><p>In <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>, a <b>transition metal alkyne complex</b> is a <a href="/wiki/Coordination_compound" class="mw-redirect" title="Coordination compound">coordination compound</a> containing one or more alkyne <a href="/wiki/Ligand" title="Ligand">ligands</a>. Such compounds are intermediates in many catalytic reactions that convert alkynes to other organic products, e.g. <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> and <a href="/wiki/Alkyne_trimerization" class="mw-redirect" title="Alkyne trimerization">trimerization</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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_alkyne_complex&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Transition metal alkyne complexes are often formed by the displacement of labile ligands by the alkyne. For example, a variety of <a href="/wiki/Dicobalt_hexacarbonyl_acetylene_complex" title="Dicobalt hexacarbonyl acetylene complex">cobalt-alkyne complexes</a> arise by the reaction of alkynes with dicobalt octacarbonyl.<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> </p> <dl><dd><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">Co<sub class="template-chem2-sub">2</sub>(CO)<sub class="template-chem2-sub">8</sub> + R<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub> → (R<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub>)Co<sub class="template-chem2-sub">2</sub>(CO)<sub class="template-chem2-sub">6</sub> + 2 CO</span></dd></dl> <p>Many alkyne complexes are produced by reduction of metal halides:<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> <dl><dd>Cp<sub>2</sub>TiCl<sub>2</sub> + Mg + Me<sub>3</sub>SiC≡CSiMe<sub>3</sub> → Cp<sub>2</sub>Ti[(CSiMe<sub>3</sub>)<sub>2</sub>] + MgCl<sub>2</sub></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_alkyne_complex&action=edit&section=2" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:VarietyPackAlkyneCmpx.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/VarietyPackAlkyneCmpx.svg/620px-VarietyPackAlkyneCmpx.svg.png" decoding="async" width="620" height="143" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/VarietyPackAlkyneCmpx.svg/930px-VarietyPackAlkyneCmpx.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/VarietyPackAlkyneCmpx.svg/1240px-VarietyPackAlkyneCmpx.svg.png 2x" data-file-width="8728" data-file-height="2014" /></a><figcaption>Structures of various metal-alkyne complexes.</figcaption></figure> <p>The coordination of alkynes to transition metals is similar to that of alkenes. The bonding is described by the <a href="/wiki/Dewar%E2%80%93Chatt%E2%80%93Duncanson_model" title="Dewar–Chatt–Duncanson model">Dewar–Chatt–Duncanson model</a>. Upon complexation the C-C bond elongates and the alkynyl carbon bends away from 180º. For example, in the phenylpropyne complex Pt(PPh<sub>3</sub>)<sub>2</sub>(MeC<sub>2</sub>Ph), the C-C distance is 1.277(25) vs 1.20 Å for a typical alkyne. The C-C-C angle distorts 40° from linearity upon complexation.<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> Because the bending induced by complexation, strained alkynes such as cycloheptyne and cyclooctyne are stabilized by complexation.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>The C≡C vibration of alkynes occurs near 2300 cm<sup>−1</sup> in the IR spectrum. This mode shifts upon complexation to around 1800 cm<sup>−1</sup>, indicating a weakening of the C-C bond. </p> <div class="mw-heading mw-heading3"><h3 id="η2-coordination_to_a_single_metal_center"><span id=".CE.B72-coordination_to_a_single_metal_center"></span>η<sup>2</sup>-coordination to a single metal center</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_alkyne_complex&action=edit&section=3" title="Edit section: η2-coordination to a single metal center"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When bonded side-on to a single metal atom, an alkyne serves as a dihapto usually two-electron donor. For early metal complexes, e.g., Cp<sub>2</sub>Ti(C<sub>2</sub>R<sub>2</sub>), strong π-backbonding into one of the π* antibonding orbitals of the alkyne is indicated. This complex is described as a metallacyclopropene derivative of Ti(IV). For late transition metal complexes, e.g., Pt(PPh<sub>3</sub>)<sub>2</sub>(MeC<sub>2</sub>Ph), the π-backbonding is less prominent, and the complex is assigned oxidation state 0.<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><sup id="cite_ref-Crabtree_7-0" class="reference"><a href="#cite_note-Crabtree-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>In some complexes, the alkyne is classified as a four-electron donor. In these cases, both pairs of pi-electrons donate to the metal. This kind of bonding was first implicated in complexes of the type W(CO)(R<sub>2</sub>C<sub>2</sub>)<sub>3</sub>.<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> </p> <div class="mw-heading mw-heading3"><h3 id="η2,_η2-coordination_bridging_two_metal_centers"><span id=".CE.B72.2C_.CE.B72-coordination_bridging_two_metal_centers"></span>η<sup>2</sup>, η<sup>2</sup>-coordination bridging two metal centers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_alkyne_complex&action=edit&section=4" title="Edit section: η2, η2-coordination bridging two metal centers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because alkynes have two π bonds, alkynes can form stable complexes in which they bridge two metal centers. The alkyne donates a total of four electrons, with two electrons donated to each of the metals. And example of a complex with this bonding scheme is η<sup>2</sup>-diphenylacetylene-(hexacarbonyl)dicobalt(0).<sup id="cite_ref-Crabtree_7-1" class="reference"><a href="#cite_note-Crabtree-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Benzyne_complexes">Benzyne complexes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_alkyne_complex&action=edit&section=5" title="Edit section: Benzyne complexes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Transition_metal_benzyne_complex" title="Transition metal benzyne complex">Transition metal benzyne complexes</a> represent a special case of alkyne complexes since the free benzynes are not stable in the absence of the metal.<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="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_alkyne_complex&action=edit&section=6" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metal alkyne complexes are intermediates in the semi<a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> of alkynes to alkenes: </p> <dl><dd>C<sub>2</sub>R<sub>2</sub> + H<sub>2</sub> → <i>cis</i>-C<sub>2</sub>R<sub>2</sub>H<sub>2</sub></dd></dl> <p>This transformation is conducted on a large scale in refineries, which unintentionally produce acetylene during the production of ethylene. It is also useful in the preparation of fine chemicals. <a href="/wiki/Semihydrogenation" class="mw-redirect" title="Semihydrogenation">Semihydrogenation</a> affords cis alkenes.<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> </p><p>Metal-alkyne complexes are also intermediates in the metal-catalyzed <a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">trimerization</a> and tetramerizations. <a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a> is produced from acetylene via the intermediacy of metal alkyne complexes. Variants of this reaction are exploited for some syntheses of substituted <a href="/wiki/Pyridine" title="Pyridine">pyridines</a>. </p><p>The <a href="/wiki/Pauson%E2%80%93Khand_reaction" title="Pauson–Khand reaction">Pauson–Khand reaction</a> provides a route to cyclopentenones via the intermediacy of cobalt-alkyne complexes. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:Pauson_Khand_reaction_original.svg" class="mw-file-description" title="PK reaction"><img alt="PK reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Pauson_Khand_reaction_original.svg/338px-Pauson_Khand_reaction_original.svg.png" decoding="async" width="338" height="114" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Pauson_Khand_reaction_original.svg/507px-Pauson_Khand_reaction_original.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/Pauson_Khand_reaction_original.svg/676px-Pauson_Khand_reaction_original.svg.png 2x" data-file-width="338" data-file-height="114" /></a><figcaption>PK reaction</figcaption></figure> <p><a href="/wiki/Acrylic_acid" title="Acrylic acid">Acrylic acid</a> was once prepared by the <a href="/wiki/Hydrocarboxylation" class="mw-redirect" title="Hydrocarboxylation">hydrocarboxylation</a> of acetylene:<sup id="cite_ref-Ullmann_11-0" class="reference"><a href="#cite_note-Ullmann-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>C<sub>2</sub>H<sub>2</sub> + H<sub>2</sub>O + CO → H<sub>2</sub>C=CHCO<sub>2</sub>H</dd></dl> <p>With the shift away from coal-based (acetylene) to petroleum-based feedstocks (olefins), catalytic reactions with alkynes are not widely practiced industrially. </p><p><a href="/wiki/Polyacetylene" title="Polyacetylene">Polyacetylene</a> has been produced using metal catalysis involving alkyne complexes. </p> <dl><dd><figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Ziegler_natta_scheme_for_polyacetylene.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Ziegler_natta_scheme_for_polyacetylene.png/220px-Ziegler_natta_scheme_for_polyacetylene.png" decoding="async" width="220" height="42" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Ziegler_natta_scheme_for_polyacetylene.png/330px-Ziegler_natta_scheme_for_polyacetylene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Ziegler_natta_scheme_for_polyacetylene.png/440px-Ziegler_natta_scheme_for_polyacetylene.png 2x" data-file-width="722" data-file-height="137" /></a><figcaption>Ti-catalyzed polymerization of <a href="/wiki/Acetylene" title="Acetylene">acetylene</a>, inspired by <a href="/wiki/Ziegler%E2%80%93Natta_catalysis" class="mw-redirect" title="Ziegler–Natta catalysis">Ziegler–Natta catalysis</a>.</figcaption></figure></dd></dl> <p><a href="/wiki/Cuprous_chloride" class="mw-redirect" title="Cuprous chloride">Cuprous chloride</a> also catalyzes the <a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">dimerization</a> of <a href="/wiki/Acetylene" title="Acetylene">acetylene</a> to <a href="/wiki/Vinylacetylene" title="Vinylacetylene">vinylacetylene</a>, once used as a precursor to various polymers such a <a href="/wiki/Neoprene" title="Neoprene">neoprene</a>. Mechanistic studies suggest that this reaction proceeds by insertion of acetylene into a copper(I) <a href="/wiki/Acetylide" title="Acetylide">acetylide</a> complex.<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> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_alkyne_complex&action=edit&section=7" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <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">Elschenbroich, C. ”Organometallics” 2006 Wiley-VCH: Weinheim. <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/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3-527-29390-6" title="Special:BookSources/3-527-29390-6">3-527-29390-6</a>.</span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">Kemmitt, R. D. W.; Russell, D. R.; "Cobalt" in <i>Comprehensive Organometallic Chemistry I</i>; Abel, E.W.; Stone, F.G.A.; Wilkinson, G. eds., 1982, Pergamon Press, Oxford. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-08-025269-9" title="Special:BookSources/0-08-025269-9">0-08-025269-9</a></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRosenthalBurlakovArndtBaumann2003" class="citation journal cs1">Rosenthal, Uwe; Burlakov, Vladimir V.; Arndt, Perdita; Baumann, Wolfgang; Spannenberg, Anke (2003). 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William; Payne, N. C. (1975). "Studies on Metal-Acetylene Complexes: V. Crystal and Molecular Structure of Bis(triphenylphosphine)(1-phenylpropyne)platinum(0), [P(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>]<sub>2</sub>(C<sub>6</sub>H<sub>5</sub>CCCH<sub>3</sub>)Pt<sup>0</sup>". <i>J. Organomet. Chem</i>. <b>99</b>: 315. <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%2FS0022-328X%2800%2988462-4">10.1016/S0022-328X(00)88462-4</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Organomet.+Chem.&rft.atitle=Studies+on+Metal-Acetylene+Complexes%3A+V.+Crystal+and+Molecular+Structure+of+Bis%28triphenylphosphine%29%281-phenylpropyne%29platinum%280%29%2C+%5BP%28C%3Csub%3E6%3C%2Fsub%3EH%3Csub%3E5%3C%2Fsub%3E%29%3Csub%3E3%3C%2Fsub%3E%5D%3Csub%3E2%3C%2Fsub%3E%28C%3Csub%3E6%3C%2Fsub%3EH%3Csub%3E5%3C%2Fsub%3ECCCH%3Csub%3E3%3C%2Fsub%3E%29Pt%3Csup%3E0%3C%2Fsup%3E&rft.volume=99&rft.pages=315&rft.date=1975&rft_id=info%3Adoi%2F10.1016%2FS0022-328X%2800%2988462-4&rft.aulast=Davies&rft.aufirst=B.+William&rft.au=Payne%2C+N.+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+alkyne+complex" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBennettSchwemlein1989" class="citation journal cs1">Bennett, Martin A.; Schwemlein, Heinz P. 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Engl.</a></i> <b>28</b> (10): 1296–1320. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.198912961">10.1002/anie.198912961</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.+Engl.&rft.atitle=Metal+Complexes+of+Small+Cycloalkynes+and+Arynes&rft.volume=28&rft.issue=10&rft.pages=1296-1320&rft.date=1989&rft_id=info%3Adoi%2F10.1002%2Fanie.198912961&rft.aulast=Bennett&rft.aufirst=Martin+A.&rft.au=Schwemlein%2C+Heinz+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+alkyne+complex" 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">Hill, A.F. <i>Organotransition Metal Chemistry</i>, 2002, Royal Society of Chemistry, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-28163-8" title="Special:BookSources/0-471-28163-8">0-471-28163-8</a>.</span> </li> <li id="cite_note-Crabtree-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Crabtree_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Crabtree_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Crabtree, R. 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Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a05_217">10.1002/14356007.a05_217</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Carbonylation&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft_id=info%3Adoi%2F10.1002%2F14356007.a05_217&rft.isbn=978-3527306732&rft.au=W.+Bertleff&rft.au=M.+Roeper&rft.au=X.+Sava&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+alkyne+complex" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTrotuşZimmermannSchüth2014" class="citation journal cs1">Trotuş, Ioan-Teodor; Zimmermann, Tobias; Schüth, Ferdi (2014). <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr400357r">"Catalytic Reactions of Acetylene: A Feedstock for the Chemical Industry Revisited"</a>. <i>Chemical Reviews</i>. <b>114</b> (3): 1761–1782. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr400357r">10.1021/cr400357r</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24228942">24228942</a>.</cite><span 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title="Ligand field theory">Ligand field theory</a></li> <li><a href="/wiki/18-electron_rule" title="18-electron rule">18-electron rule</a></li> <li><a href="/wiki/D_electron_count" title="D electron count">d electron count</a></li> <li><a href="/wiki/Polyhedral_skeletal_electron_pair_theory" title="Polyhedral skeletal electron pair theory">Polyhedral skeletal electron pair theory</a></li> <li><a href="/wiki/Isolobal_principle" title="Isolobal principle">Isolobal principle</a></li> <li><a href="/wiki/Pi_backbonding" title="Pi backbonding">π backbonding</a></li> <li><a href="/wiki/Dewar%E2%80%93Chatt%E2%80%93Duncanson_model" title="Dewar–Chatt–Duncanson model">Dewar–Chatt–Duncanson model</a></li> <li><a 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 class="mw-selflink selflink">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="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 class="mw-selflink selflink">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=Transition_metal_alkyne_complex&oldid=1223592523#Applications">https://en.wikipedia.org/w/index.php?title=Transition_metal_alkyne_complex&oldid=1223592523#Applications</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_chemistry" title="Category:Organometallic chemistry">Organometallic chemistry</a></li><li><a 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