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Transition metal formyl complex - Wikipedia

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href="/wiki/File:CaRe(PPh3)(NO)(CHO)FMCPRE.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/CaRe%28PPh3%29%28NO%29%28CHO%29FMCPRE.png/220px-CaRe%28PPh3%29%28NO%29%28CHO%29FMCPRE.png" decoding="async" width="220" height="234" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/CaRe%28PPh3%29%28NO%29%28CHO%29FMCPRE.png/330px-CaRe%28PPh3%29%28NO%29%28CHO%29FMCPRE.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2f/CaRe%28PPh3%29%28NO%29%28CHO%29FMCPRE.png/440px-CaRe%28PPh3%29%28NO%29%28CHO%29FMCPRE.png 2x" data-file-width="634" data-file-height="675" /></a><figcaption>Structure of the formyl complex CpRe(PPh<sub>3</sub>)(NO)CHO. Selected distances: d<sub>HC-O</sub> = 122.1, d<sub>HC-Re</sub> = 205.5, d<sub>ON-Re</sub> = 177.7 pm.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup></figcaption></figure> <p>In <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>, a <b>transition metal formyl complex</b> is a metal complex containing one (usually) or more <a href="/wiki/Formyl" class="mw-redirect" title="Formyl">formyl</a> (CHO) ligand. A subset of <a href="/wiki/Transition_metal_acyl_complexes" title="Transition metal acyl complexes">transition metal acyl complexes</a>, formyl complexes can be viewed as metalla-aldehydes. A representative example is (CO)<sub>5</sub>ReCHO. The formyl is viewed as an X (pseudohalide) ligand. Metal formyls are proposed as intermediates in the hydrogenation of <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a>, as occurs in the <a href="/wiki/Fischer-Tropsch_process" class="mw-redirect" title="Fischer-Tropsch process">Fischer-Tropsch process</a>.<sup id="cite_ref-JAG_2-0" class="reference"><a href="#cite_note-JAG-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> </p> <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_formyl_complex&amp;action=edit&amp;section=1" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The MCHO group is planar. A C=O <a href="/wiki/Double_bond" title="Double bond">double bond</a> is indicated by <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a>. A second resonance structure has a M=C double bond, with negative charge on oxygen. </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis_and_reactions">Synthesis and reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_formyl_complex&amp;action=edit&amp;section=2" title="Edit section: Synthesis and reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metal formyl complexes are often prepared by the reaction of metal carbonyls with hydride reagents:<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p> <dl><dd>[Re(CO)<sub>6</sub>]<sup>+</sup> + H<sup>−</sup> → (CO)<sub>5</sub>ReCHO</dd></dl> <p>The CO ligand is the electrophile and the hydride (provided typically from a <a href="/wiki/Borohydride" title="Borohydride">borohydride</a>) is the nucleophile. </p><p>Some metal formyls are produced by reaction of metal carbonyl anions with reagents that donate the equivalent of a formyl cation, such a mixed formate anhydrides.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> </p><p>Metal formyls participate in many reactions, many of which are motivated by interest in Fischer-Tropsch chemistry. O-alkylation gives carbenoid complexes. The formyl ligand also functions as a base, allowing the formation of M-CH=O-M' linkages.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> Decarbonylation leads to de-insertion of the carbonyl, yielding hydride complexes.<sup id="cite_ref-JAG_2-1" class="reference"><a href="#cite_note-JAG-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_formyl_complex&amp;action=edit&amp;section=3" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap"><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="CITEREFWongTamStrouseGladysz1979" class="citation journal cs1">Wong, Wai-Kwok; Tam, Wilson; Strouse, C. E.; Gladysz, J. A. (1979). "X-Ray crystal structure and chemical transformations of the neutral metal formyl &#91;(η-C5H5)Re(PPh3)(NO)(CHO)&#93;". <i>J. Chem. Soc., Chem. Commun.</i> (12): 530–532. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC39790000530">10.1039/C39790000530</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=J.+Chem.+Soc.%2C+Chem.+Commun.&amp;rft.atitle=X-Ray+crystal+structure+and+chemical+transformations+of+the+neutral+metal+formyl+%26%2391%3B%28%CE%B7-C5H5%29Re%28PPh3%29%28NO%29%28CHO%29%26%2393%3B&amp;rft.issue=12&amp;rft.pages=530-532&amp;rft.date=1979&amp;rft_id=info%3Adoi%2F10.1039%2FC39790000530&amp;rft.aulast=Wong&amp;rft.aufirst=Wai-Kwok&amp;rft.au=Tam%2C+Wilson&amp;rft.au=Strouse%2C+C.+E.&amp;rft.au=Gladysz%2C+J.+A.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+formyl+complex" class="Z3988"></span></span> </li> <li id="cite_note-JAG-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-JAG_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-JAG_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGladysz1982" class="citation book cs1">Gladysz, J.A. (1982). <i>Transition Metal Formyl Complexes</i>. Advances in Organometallic Chemistry. Vol.&#160;20. pp.&#160;1–38. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0065-3055%2808%2960519-5">10.1016/S0065-3055(08)60519-5</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9780120311200" title="Special:BookSources/9780120311200"><bdi>9780120311200</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Transition+Metal+Formyl+Complexes&amp;rft.series=Advances+in+Organometallic+Chemistry&amp;rft.pages=1-38&amp;rft.date=1982&amp;rft_id=info%3Adoi%2F10.1016%2FS0065-3055%2808%2960519-5&amp;rft.isbn=9780120311200&amp;rft.aulast=Gladysz&amp;rft.aufirst=J.A.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+formyl+complex" class="Z3988"></span></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="CITEREFMaityTeets2016" class="citation journal cs1">Maity, Ayan; Teets, Thomas S. (2016). "Main Group Lewis Acid-Mediated Transformations of Transition-Metal Hydride Complexes". <i>Chemical Reviews</i>. <b>116</b> (15): 8873–8911. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.chemrev.6b00034">10.1021/acs.chemrev.6b00034</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27164024">27164024</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Chemical+Reviews&amp;rft.atitle=Main+Group+Lewis+Acid-Mediated+Transformations+of+Transition-Metal+Hydride+Complexes&amp;rft.volume=116&amp;rft.issue=15&amp;rft.pages=8873-8911&amp;rft.date=2016&amp;rft_id=info%3Adoi%2F10.1021%2Facs.chemrev.6b00034&amp;rft_id=info%3Apmid%2F27164024&amp;rft.aulast=Maity&amp;rft.aufirst=Ayan&amp;rft.au=Teets%2C+Thomas+S.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+formyl+complex" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCollmanWinter1973" class="citation journal cs1">Collman, J. P.; Winter, S. R. (1973). "Isolation and Characterization of a Kinetically Stable transition Metal Formyl complex". <i>Journal of the American Chemical Society</i>. <b>95</b> (12): 4089–4090. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00793a066">10.1021/ja00793a066</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+the+American+Chemical+Society&amp;rft.atitle=Isolation+and+Characterization+of+a+Kinetically+Stable+transition+Metal+Formyl+complex&amp;rft.volume=95&amp;rft.issue=12&amp;rft.pages=4089-4090&amp;rft.date=1973&amp;rft_id=info%3Adoi%2F10.1021%2Fja00793a066&amp;rft.aulast=Collman&amp;rft.aufirst=J.+P.&amp;rft.au=Winter%2C+S.+R.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+formyl+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="CITEREFChenSchmalleFoxBerke2005" class="citation journal cs1">Chen, Zilu; Schmalle, Helmut W.; Fox, Thomas; Berke, Heinz (2005). "Insertion Reactions of Hydridonitrosyltetrakis(trimethylphosphine) Tungsten(0)". <i>Dalton Transactions</i> (3): 580–587. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fb414943b">10.1039/b414943b</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15672204">15672204</a>.</cite><span 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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 class="mw-selflink selflink">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> &amp; 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&#39;-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&amp;action=edit&amp;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&amp;action=edit&amp;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&amp;action=edit&amp;redlink=1" class="new" title="Iodo complex (page does not exist)">I<sup>−</sup></a></li></ul> </div></td></tr></tbody></table></div> <!-- NewPP limit report Parsed by mw‐api‐ext.eqiad.main‐69c9bb5b64‐k56hn Cached time: 20241128130055 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1] CPU time usage: 0.214 seconds Real time usage: 0.513 seconds Preprocessor visited node count: 379/1000000 Post‐expand include size: 31937/2097152 bytes Template argument size: 0/2097152 bytes Highest expansion depth: 5/100 Expensive parser function count: 1/500 Unstrip recursion depth: 1/20 Unstrip post‐expand size: 26467/5000000 bytes Lua time usage: 0.149/10.000 seconds Lua memory usage: 3855727/52428800 bytes 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