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Transition metal complexes of 1,10-phenanthroline - Wikipedia
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dir="ltr"><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:CSD_CIF_JEXXEQ.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/CSD_CIF_JEXXEQ.jpg/220px-CSD_CIF_JEXXEQ.jpg" decoding="async" width="220" height="201" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/CSD_CIF_JEXXEQ.jpg/330px-CSD_CIF_JEXXEQ.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/34/CSD_CIF_JEXXEQ.jpg/440px-CSD_CIF_JEXXEQ.jpg 2x" data-file-width="1591" data-file-height="1457" /></a><figcaption>Structure of PtCl<sub>2</sub>(1,10-phenanthroline).<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> Color code: green = Cl, blue = N, gray = C.</figcaption></figure> <p><b>Transition metal complexes of 1,10-phenanthroline</b> ("phen") are <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complexes</a> containing one or more <a href="/wiki/1,10-Phenanthroline" title="1,10-Phenanthroline">1,10-phenanthroline</a> <a href="/wiki/Ligand" title="Ligand">ligands</a>.<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> Complexes have been described for many <a href="/wiki/Transition_metal" title="Transition metal">transition metals</a>. In almost all complexes, phen serves as a <a href="/wiki/Bidentate_ligand" class="mw-redirect" title="Bidentate ligand">bidentate ligand</a>, binding metal centers with the two nitrogen atoms. Examples include PtCl<sub>2</sub>(phen) and [Fe(phen)<sub>3</sub>]<sup>2+</sup>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Homoleptic_complexes">Homoleptic complexes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_complexes_of_1,10-phenanthroline&action=edit&section=1" title="Edit section: Homoleptic complexes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several <a href="/wiki/Homoleptic_complex" class="mw-redirect" title="Homoleptic complex">homoleptic complexes</a> are known of the type [M(phen)<sub>3</sub>]<sup>2+</sup>. Particularly well studied is [Fe(phen)<sub>3</sub>]<sup>2+</sup>, called "<a href="/wiki/Ferroin" title="Ferroin">ferroin</a>." It can be used for the <a href="/wiki/Spectrophotometry" title="Spectrophotometry">photometric</a> determination of Fe(II).<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> It is used as a <a href="/wiki/Redox_indicator" title="Redox indicator">redox indicator</a> with <a href="/wiki/Standard_potential" class="mw-redirect" title="Standard potential">standard potential</a> +1.06 V. The reduced ferrous form has a deep red colour and the oxidised form is light-blue.<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> The pink complex [Ni(phen)<sub>3</sub>]<sup>2+</sup> has been resolved into its <a href="/wiki/%CE%94_and_%CE%9B_isomer" class="mw-redirect" title="Δ and Λ isomer">Δ and Λ isomers</a>.<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>Copper(I) forms [Cu(phen)<sub>2</sub>]<sup>+</sup>, which is <a href="/wiki/Luminescent" class="mw-redirect" title="Luminescent">luminescent</a>.<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-Pallenberg_7-0" class="reference"><a href="#cite_note-Pallenberg-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Bioinorganic_chemistry">Bioinorganic chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_complexes_of_1,10-phenanthroline&action=edit&section=2" title="Edit section: Bioinorganic chemistry"><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:Ru(phen)2(dppz)2%2B.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Ru%28phen%292%28dppz%292%2B.svg/220px-Ru%28phen%292%28dppz%292%2B.svg.png" decoding="async" width="220" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Ru%28phen%292%28dppz%292%2B.svg/330px-Ru%28phen%292%28dppz%292%2B.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Ru%28phen%292%28dppz%292%2B.svg/440px-Ru%28phen%292%28dppz%292%2B.svg.png 2x" data-file-width="335" data-file-height="229" /></a><figcaption>Structure of the metallointercalator [Ru(phen)<sub>2</sub>(dppz)]<sup>2+</sup> (dppz = dipyrido[3,2-a:2‘,3‘-c]phenazine).</figcaption></figure> <p>It has long been known that some cationic metal-phen complexes <a href="/wiki/Intercalation_(chemistry)" title="Intercalation (chemistry)">intercalate</a> into DNA.<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> These <b>metallointercalators</b> associate <a href="/wiki/Enantioselective" class="mw-redirect" title="Enantioselective">enantioselectively</a> and exhibit distinctive optical properties.<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><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>1,10-Phenanthroline is an <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitor</a> of <a href="/wiki/Metallopeptidase" class="mw-redirect" title="Metallopeptidase">metallopeptidases</a>, with one of the first observed instances reported in <a href="/wiki/Carboxypeptidase_A" title="Carboxypeptidase A">carboxypeptidase A</a>.<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> Inhibition of the enzyme occurs by removal and chelation of the metal ion required for catalytic activity, leaving an inactive <a href="/wiki/Apoenzyme" class="mw-redirect" title="Apoenzyme">apoenzyme</a>. 1,10-Phenanthroline targets mainly zinc metallopeptidases, with a much lower affinity for calcium.<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 class="mw-heading mw-heading2"><h2 id="Modified_phen_ligands">Modified phen ligands</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_complexes_of_1,10-phenanthroline&action=edit&section=3" title="Edit section: Modified phen ligands"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A variety of substituted derivatives of phen have been examined as ligands.<sup id="cite_ref-Pallenberg_7-1" class="reference"><a href="#cite_note-Pallenberg-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><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> Substituents at the 2,9 positions confer protection for the attached metal, inhibiting the binding of multiple equivalents of the phenanthroline. Such <a href="/wiki/Bulky_ligand" class="mw-redirect" title="Bulky ligand">bulky ligands</a> also favor <a href="/wiki/Trigonal_coordination" class="mw-redirect" title="Trigonal coordination">trigonal</a> or <a href="/wiki/Tetrahedral_coordination" class="mw-redirect" title="Tetrahedral coordination">tetrahedral coordination</a> at the metal.<sup id="cite_ref-Ruben_14-0" class="reference"><a href="#cite_note-Ruben-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Phen itself form complexes of the type [M(phen)<sub>3</sub>]Cl<sub>2</sub> when treated with metal dihalides (M = Fe, Co, Ni). By contrast, <a href="/wiki/Neocuproine" title="Neocuproine">neocuproine</a> and <a href="/wiki/Bathocuproine" title="Bathocuproine">bathocuproine</a> form 1:1 complexes such as [Ni(neocuproine)Cl<sub>2</sub>]<sub>2</sub>.<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> </p> <table class="wikitable"> <caption>Basicities of 1,10-Phenanthrolines and 2,2'-Bipyridine<sup id="cite_ref-pKa_16-0" class="reference"><a href="#cite_note-pKa-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th>phen derivative </th> <th>pK<sub>a</sub> </th> <th>comment/alt. name </th> <th>numbering scheme </th></tr> <tr> <td>1,10-phenanthroline</td> <td>4.86</td> <td>phen</td> <td rowspan="11"><span typeof="mw:File/Frameless"><a href="/wiki/File:Phenanthroline_Numbering.png" class="mw-file-description" title="Numbering for 1,10-phenanthroline derivatives."><img alt="Numbering for 1,10-phenanthroline derivatives." src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Phenanthroline_Numbering.png/150px-Phenanthroline_Numbering.png" decoding="async" width="150" height="235" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Phenanthroline_Numbering.png/225px-Phenanthroline_Numbering.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/Phenanthroline_Numbering.png/300px-Phenanthroline_Numbering.png 2x" data-file-width="301" data-file-height="472" /></a></span> </td></tr> <tr> <td><a href="/wiki/Bipy" class="mw-redirect" title="Bipy">2,2'-bipyridine</a></td> <td>4.30</td> <td>bipy </td></tr> <tr> <td>5-nitro-1,10-phenanthroline</td> <td>3.57 </td></tr> <tr> <td>2,9-dimethyl-1,10-phenanthroline</td> <td>unknown</td> <td><a href="/wiki/Neocuproine" title="Neocuproine">neocuproine</a><sup id="cite_ref-Watson_17-0" class="reference"><a href="#cite_note-Watson-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><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> </td></tr> <tr> <td>2,9-Dimethyl-4,7-diphenylphenanthroline</td> <td>unknown</td> <td><a href="/wiki/Bathocuproine" title="Bathocuproine">Bathocuproine</a><sup id="cite_ref-Watson_17-1" class="reference"><a href="#cite_note-Watson-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><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> </td></tr> <tr> <td>4,7-dimethyl-1,10-phenanthroline</td> <td>5.97 </td></tr> <tr> <td>4,7-diphenyl-1,10-phenanthroline</td> <td>unknown</td> <td>bathophenanthroline<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> </td></tr> <tr> <td>5,6-dimethyl-1,10-phenanthroline</td> <td>5.20</td> <td>5,6-Me<sub>2</sub>phen </td></tr> <tr> <td>3,4,7,8-tetramethylphenanthroline</td> <td>6.31</td> <td>3,4,7,8-Me<sub>4</sub>phen<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> </td></tr> <tr> <td>4,7-dimethoxy-1,10-phenanthroline</td> <td>6.45</td> <td>4,7-(MeO)<sub>2</sub>phen<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> </td></tr> <tr> <td>2,6-dimesitylphenanthroline</td> <td>unknown</td> <td>HETPHEN<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><sup id="cite_ref-Ruben_14-1" class="reference"><a href="#cite_note-Ruben-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <p><a href="/wiki/1,10-Phenanthroline-5,6-dione" title="1,10-Phenanthroline-5,6-dione">1,10-Phenanthroline-5,6-dione</a> is a phen-type ligand incorporating an <a href="/wiki/1,2-Benzoquinone" title="1,2-Benzoquinone">ortho-quinone</a> group.<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> <div class="mw-heading mw-heading2"><h2 id="Comparison_with_bipyridine">Comparison with bipyridine</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_complexes_of_1,10-phenanthroline&action=edit&section=4" title="Edit section: Comparison with bipyridine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Complexes of phen and those of <a href="/wiki/2,2%27-Bipyridine" class="mw-redirect" title="2,2'-Bipyridine">2,2'-bipyridine</a> (bipyr) are similar: the metal-ligand ensemble is planar, which facilitates <a href="/wiki/Electron_delocalization" class="mw-redirect" title="Electron delocalization">electron delocalization</a>. As a consequence of this delocalization, phen complexes often exhibit distinctive optical and redox properties. With respective p<i>K</i><sub>a</sub>'s of 4.86 and 4.3 for their <a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">conjugate acids</a>, phenanthroline and bipy are of comparable <a href="/wiki/Basicity" class="mw-redirect" title="Basicity">basicity</a>.<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> In phenanthroline, the two nitrogen donors are preorganized for <a href="/wiki/Chelation" title="Chelation">chelation</a>. According to one ligand ranking scale, phen is a weaker donor than bipy.<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> <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_complexes_of_1,10-phenanthroline&action=edit&section=5" 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="CITEREFGrzesiakMatzger2007" class="citation journal cs1">Grzesiak, Adam L.; Matzger, Adam J. 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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: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 class="mw-selflink selflink">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> <!-- NewPP limit report Parsed by mw‐api‐int.codfw.main‐849f99967d‐c8z6k Cached time: 20241123130647 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.467 seconds Real time usage: 0.533 seconds Preprocessor visited node count: 1651/1000000 Post‐expand include size: 79483/2097152 bytes Template argument size: 114/2097152 bytes Highest expansion depth: 11/100 Expensive parser function count: 1/500 Unstrip recursion depth: 1/20 Unstrip post‐expand size: 107208/5000000 bytes Lua time usage: 0.315/10.000 seconds Lua memory usage: 3979301/52428800 bytes Number of Wikibase entities loaded: 0/400 --> <!-- Transclusion expansion time report (%,ms,calls,template) 100.00% 441.807 1 -total 73.27% 323.718 1 Template:Reflist 52.79% 233.230 19 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