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Transition metal complexes of 2,2'-bipyridine - Wikipedia

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<div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><p><b>Transition metal complexes of 2,2'-bipyridine</b> are <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complexes</a> containing one or more <a href="/wiki/2,2%27-Bipyridine" class="mw-redirect" title="2,2&#39;-Bipyridine">2,2'-bipyridine</a> <a href="/wiki/Ligand" title="Ligand">ligands</a>. Complexes have been described for all of the transition metals. <sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (August 2023)">citation needed</span></a></i>&#93;</sup> Although few have any practical value, these complexes have been influential.<sup id="cite_ref-Constacraft_1-0" class="reference"><a href="#cite_note-Constacraft-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> 2,2'-Bipyridine (bipy) is classified as a <a href="/wiki/Diimine_ligand" class="mw-redirect" title="Diimine ligand">diimine ligand</a>. Unlike the structures of <a href="/wiki/Pyridine_complex" class="mw-redirect" title="Pyridine complex">pyridine complexes</a>, the two rings in bipy are coplanar, which facilitates electron delocalization. As a consequence of this delocalization, bipy complexes often exhibit distinctive optical and redox properties. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Complexes">Complexes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_complexes_of_2,2%27-bipyridine&amp;action=edit&amp;section=1" title="Edit section: Complexes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Bipy forms a wide variety of complexes. Almost always, it is a bidentate ligand, binding metal centers with the two nitrogen atoms. Examples: </p> <ul><li>Mo(CO)<sub>4</sub>(bipy), derived from <a href="/wiki/Molybdenum_carbonyl" class="mw-redirect" title="Molybdenum carbonyl">Mo(CO)<sub>6</sub></a>.<sup id="cite_ref-Constacraft_1-1" class="reference"><a href="#cite_note-Constacraft-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup></li> <li><a href="/wiki/Cis-Dichlorobis(bipyridine)ruthenium(II)" title="Cis-Dichlorobis(bipyridine)ruthenium(II)">RuCl<sub>2</sub>(bipy)<sub>2</sub></a>,<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> a popular precursor to mixed ligand complexes.</li> <li><a href="/wiki/Ruthenium_tris(bipyridine)_chloride" class="mw-redirect" title="Ruthenium tris(bipyridine) chloride">[Ru(bipy)<sub>3</sub>]<sup>2+</sup></a>, a well studied <a href="/wiki/Luminophore" title="Luminophore">luminophore</a>.</li> <li><a href="/wiki/Tris(bipyridine)iron(II)_chloride" title="Tris(bipyridine)iron(II) chloride">[Fe(bipy)<sub>3</sub>]<sup>2+</sup></a> has been used for the <a href="/wiki/Colorimetric_analysis" title="Colorimetric analysis">colorimetric analysis</a> of iron ions.</li> <li>{[Ru(bipyridine)<sub>2</sub>(OH<sub>2</sub>)]<sub>2</sub>(O)}<sup>2+</sup>, "ruthenium blue" has attracted academic interest as a rare complex that catalyzes the <a href="/wiki/Water_oxidation_catalysis" title="Water oxidation catalysis">oxidation of water</a>.<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></li></ul> <div class="mw-heading mw-heading3"><h3 id="Tris-bipy_complexes">Tris-bipy complexes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_complexes_of_2,2%27-bipyridine&amp;action=edit&amp;section=2" title="Edit section: Tris-bipy complexes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Fe-Bipy-3.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Fe-Bipy-3.png/220px-Fe-Bipy-3.png" decoding="async" width="220" height="203" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Fe-Bipy-3.png/330px-Fe-Bipy-3.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Fe-Bipy-3.png/440px-Fe-Bipy-3.png 2x" data-file-width="1000" data-file-height="924" /></a><figcaption>Three-dimensional view of the [Fe(bipy)<sub>3</sub>]<sup>2+</sup> complex.</figcaption></figure> <p>Bipyridine complexes <a href="/wiki/UV/VIS_spectroscopy" class="mw-redirect" title="UV/VIS spectroscopy">absorb</a> intensely in the visible part of the spectrum. The electronic transitions are attributed to metal-to-ligand <a href="/wiki/Charge_transfer_complex" class="mw-redirect" title="Charge transfer complex">charge transfer</a> (MLCT). In the "tris(bipy) complexes" three bipyridine molecules coordinate to a metal ion, written as [M(bipy)<sub>3</sub>]<sup><i>n</i>+</sup> (M = metal ion; Cr, Fe, Co, Ru, Rh and so on). These complexes have six-coordinated, <a href="/wiki/Octahedral_molecular_geometry" title="Octahedral molecular geometry">octahedral</a> structures and exists as <a href="/wiki/Enantiomer" title="Enantiomer">enantiomeric</a> pairs: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Bpycomp.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Bpycomp.png/250px-Bpycomp.png" decoding="async" width="250" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Bpycomp.png/375px-Bpycomp.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Bpycomp.png/500px-Bpycomp.png 2x" data-file-width="950" data-file-height="522" /></a></span></dd></dl> <p>These and other <a href="/wiki/Homoleptic" class="mw-redirect" title="Homoleptic">homoleptic</a> tris-2,2′-bipy complexes of many transition <a href="/wiki/Metals" class="mw-redirect" title="Metals">metals</a> are electroactive. Often, both the <a href="/wiki/Metal" title="Metal">metal</a> centred and ligand centred electrochemical reactions are reversible one-<a href="/wiki/Electron" title="Electron">electron</a> reactions that can be observed by <a href="/wiki/Cyclic_voltammetry" title="Cyclic voltammetry">cyclic voltammetry</a>. Under strongly reducing conditions, some tris(bipy) complexes can be reduced to neutral derivatives containing bipy<sup>−</sup> ligands. Examples include M(bipy)<sub>3</sub>, where M = Al, Cr, Si.<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> <div class="mw-heading mw-heading3"><h3 id="Square_planar_complexes">Square planar complexes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_complexes_of_2,2%27-bipyridine&amp;action=edit&amp;section=3" title="Edit section: Square planar complexes"><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:(Pt(bipy)2)%2B%2B_Xray_JAXQOP.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/%28Pt%28bipy%292%29%2B%2B_Xray_JAXQOP.png/220px-%28Pt%28bipy%292%29%2B%2B_Xray_JAXQOP.png" decoding="async" width="220" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/%28Pt%28bipy%292%29%2B%2B_Xray_JAXQOP.png/330px-%28Pt%28bipy%292%29%2B%2B_Xray_JAXQOP.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/%28Pt%28bipy%292%29%2B%2B_Xray_JAXQOP.png/440px-%28Pt%28bipy%292%29%2B%2B_Xray_JAXQOP.png 2x" data-file-width="490" data-file-height="186" /></a><figcaption>Structure of [Pt(bipy)<sub>2</sub>]<sup>2+</sup> as determined by <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a>.<sup id="cite_ref-McInnes_5-0" class="reference"><a href="#cite_note-McInnes-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup></figcaption></figure> <p>Square planar complexes of the type [Pt(bipy)<sub>2</sub>]<sup>2+</sup> react with nucleophiles because of the steric clash between the 6,6' positions between the pair of bipy ligands. This clash is indicated by the bowing of the pyridyl rings out of the plane defined by PtN<sub>4</sub>.<sup id="cite_ref-McInnes_5-1" class="reference"><a href="#cite_note-McInnes-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Related_ligands">Related ligands</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Transition_metal_complexes_of_2,2%27-bipyridine&amp;action=edit&amp;section=4" title="Edit section: Related ligands"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many ring-substituted variants of bipy have been described, especially <a href="/wiki/Dimethyl-2,2%27-bipyridine" title="Dimethyl-2,2&#39;-bipyridine">dimethyl-2,2'-bipyridines</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> Alkyl substituents enhance the solubility of the complexes in organic solvents. 6,6'-Substituents tend to protect the metal center.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> </p><p>The related <i>N</i>,<i>N</i>-heterocyclic ligand <a href="/wiki/Phenanthroline" class="mw-redirect" title="Phenanthroline">phenanthroline</a> forms similar complexes. With respective p<i>K</i><sub>a</sub>'s of 4.86 and 4.3 for their conjugate acids, phenanthroline and bipy are of comparable basicity.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> </p><p><a href="/wiki/2,2%27-Biquinoline" title="2,2&#39;-Biquinoline">2,2'-Biquinoline</a> is closely related to bipy as a ligand. </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_2,2%27-bipyridine&amp;action=edit&amp;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"><ol class="references"> <li id="cite_note-Constacraft-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Constacraft_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Constacraft_1-1"><sup><i><b>b</b></i></sup></a></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="CITEREFConstableHousecroft2019" class="citation journal cs1">Constable; Housecroft (2019). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6864536">"The Early Years of 2,2'-Bipyridine—A Ligand in its Own Lifetime"</a>. <i>Molecules</i>. <b>24</b> (21): 3951. <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/10.3390%2Fmolecules24213951">10.3390/molecules24213951</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6864536">6864536</a></span>. <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/31683694">31683694</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=Molecules&amp;rft.atitle=The+Early+Years+of+2%2C2%27-Bipyridine%E2%80%94A+Ligand+in+its+Own+Lifetime&amp;rft.volume=24&amp;rft.issue=21&amp;rft.pages=3951&amp;rft.date=2019&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6864536%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F31683694&amp;rft_id=info%3Adoi%2F10.3390%2Fmolecules24213951&amp;rft.au=Constable&amp;rft.au=Housecroft&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6864536&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+complexes+of+2%2C2%27-bipyridine" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLay,_P._A.Sargeson,_A._M.Taube,_H.Chou,_M._H.1986" class="citation journal cs1">Lay, P. 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"Synthesis of 4-, 5-, and 6-Methyl-2,2′-Bipyridine by a Negishi Cross-Coupling Strategy". <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>78</b>: 51. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.078.0051">10.15227/orgsyn.078.0051</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=Organic+Syntheses&amp;rft.atitle=Synthesis+of+4-%2C+5-%2C+and+6-Methyl-2%2C2%E2%80%B2-Bipyridine+by+a+Negishi+Cross-Coupling+Strategy&amp;rft.volume=78&amp;rft.pages=51&amp;rft.date=2002&amp;rft_id=info%3Adoi%2F10.15227%2Forgsyn.078.0051&amp;rft.au=Smith%2C+A.+P.&amp;rft.au=Savage%2C+S.+A.&amp;rft.au=Love%2C+J.&amp;rft.au=Fraser%2C+C.+L.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+complexes+of+2%2C2%27-bipyridine" class="Z3988"></span>.</span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBhattacharyaSebghatiVanderlindenSaouma2020" class="citation journal cs1">Bhattacharya, Moumita; Sebghati, Sepehr; Vanderlinden, Ryan T.; Saouma, Caroline T. (2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7584391">"Toward Combined Carbon Capture and Recycling: Addition of an Amine Alters Product Selectivity from CO to Formic Acid in Manganese Catalyzed Reduction of CO<sub>2</sub>"</a>. <i>Journal of the American Chemical Society</i>. <b>142</b> (41): <span class="nowrap">17589–</span>17597. <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%2Fjacs.0c07763">10.1021/jacs.0c07763</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7584391">7584391</a></span>. <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/32955864">32955864</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=Toward+Combined+Carbon+Capture+and+Recycling%3A+Addition+of+an+Amine+Alters+Product+Selectivity+from+CO+to+Formic+Acid+in+Manganese+Catalyzed+Reduction+of+CO%3Csub%3E2%3C%2Fsub%3E&amp;rft.volume=142&amp;rft.issue=41&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E17589-%3C%2Fspan%3E17597&amp;rft.date=2020&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7584391%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F32955864&amp;rft_id=info%3Adoi%2F10.1021%2Fjacs.0c07763&amp;rft.aulast=Bhattacharya&amp;rft.aufirst=Moumita&amp;rft.au=Sebghati%2C+Sepehr&amp;rft.au=Vanderlinden%2C+Ryan+T.&amp;rft.au=Saouma%2C+Caroline+T.&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7584391&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+complexes+of+2%2C2%27-bipyridine" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJ._G._LeipoldtG._J._LamprechtE._C.Steynberg1991" class="citation journal cs1">J. G. Leipoldt; G. J. Lamprecht; E. C.Steynberg (1991). "Kinetics of the Substitution of Acetylacetone in Acetylactonato-1,5-cyclooctadienerhodium(I) by Derivatives of 1,10-Phenanthroline and 2,2′-Dipyridyl". <i>Journal of Organometallic Chemistry</i>. <b>402</b> (2): <span class="nowrap">259–</span>263. <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%2F0022-328X%2891%2983069-G">10.1016/0022-328X(91)83069-G</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+Organometallic+Chemistry&amp;rft.atitle=Kinetics+of+the+Substitution+of+Acetylacetone+in+Acetylactonato-1%2C5-cyclooctadienerhodium%28I%29+by+Derivatives+of+1%2C10-Phenanthroline+and+2%2C2%E2%80%B2-Dipyridyl&amp;rft.volume=402&amp;rft.issue=2&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E259-%3C%2Fspan%3E263&amp;rft.date=1991&amp;rft_id=info%3Adoi%2F10.1016%2F0022-328X%2891%2983069-G&amp;rft.au=J.+G.+Leipoldt&amp;rft.au=G.+J.+Lamprecht&amp;rft.au=E.+C.Steynberg&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATransition+metal+complexes+of+2%2C2%27-bipyridine" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist 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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_complexes113" 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> &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 class="mw-selflink selflink">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_hydroxide_complexes" title="Transition metal hydroxide complexes">OH<sup>−</sup></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_sulfito_complex" title="Transition metal sulfito complex">SO<sub>3</sub><sup>2-</sup></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‐web.eqiad.main‐54c6f8c945‐j847p Cached time: 20250301094847 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.308 seconds Real time usage: 0.391 seconds Preprocessor visited node count: 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