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class="firstHeading mw-first-heading"><span class="mw-page-title-main">Organolanthanide chemistry</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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Unsourced material may be challenged and removed.<br /><small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Organolanthanide+chemistry%22">"Organolanthanide chemistry"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Organolanthanide+chemistry%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Organolanthanide+chemistry%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Organolanthanide+chemistry%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Organolanthanide+chemistry%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Organolanthanide+chemistry%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">May 2014</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p><b>Organolanthanide chemistry</b> is the field of <a href="/wiki/Chemistry" title="Chemistry">chemistry</a> that studies <b>organolanthanides</b>, compounds with a <a href="/wiki/Lanthanide" title="Lanthanide">lanthanide</a>-to-<a href="/wiki/Carbon" title="Carbon">carbon</a> bond. Organolanthanide compounds are different from their <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organotransition metal</a> analogues in the following ways: </p> <ul><li>They are far more air- and water-sensitive and are often <a href="/wiki/Pyrophoric" class="mw-redirect" title="Pyrophoric">pyrophoric</a>.</li> <li>Chemistry in the 0 <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation state</a> is far more limited. In fact, their electropositive nature makes their organometallic compounds more likely to be ionic.</li> <li>They form no stable <a href="/wiki/Carbonyl_complex" class="mw-redirect" title="Carbonyl complex">carbonyls</a> at room temperature; organolanthanide carbonyl compounds have been observed only in <a href="/wiki/Argon" title="Argon">argon</a> matrices, and decompose when heated to 40 <a href="/wiki/Kelvin" title="Kelvin">K</a>.</li></ul> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="σ-Bonded_complexes"><span id=".CF.83-Bonded_complexes"></span>σ-Bonded complexes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organolanthanide_chemistry&action=edit&section=1" title="Edit section: σ-Bonded complexes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metal-carbon σ bonds are found in alkyls of the lanthanide elements such as [LnMe<sub>6</sub>]<sup>3−</sup> and Ln[CH(SiMe<sub>3</sub>)<sub>2</sub>]<sub>3</sub>. <a href="/wiki/Methyllithium" title="Methyllithium">Methyllithium</a> dissolved in <a href="/wiki/THF" class="mw-redirect" title="THF">THF</a> reacts in stoichiometric ratio with LnCl<sub>3</sub> (Ln = <a href="/wiki/Yttrium" title="Yttrium">Y</a>, <a href="/wiki/Lanthanum" title="Lanthanum">La</a>) to yield Ln(CH<sub>3</sub>)<sub>3</sub> probably contaminated with <a href="/wiki/Lithium_chloride" title="Lithium chloride">LiCl</a>. </p><p>If a chelating agent (L-L), such as <a href="/wiki/Tetramethylethylenediamine" title="Tetramethylethylenediamine">tetramethylethylenediamine</a> (tmed or tmeda) or <a href="/wiki/1,2-dimethoxyethane" class="mw-redirect" title="1,2-dimethoxyethane">1,2-dimethoxyethane</a> (dme) is mixed with MCl<sub>3</sub> and CH<sub>3</sub>Li in THF, this forms [Li(tmed)]<sub>3</sub>[M(CH<sub>3</sub>)<sub>6</sub>] and [Li(dme)]<sub>3</sub>[M(CH<sub>3</sub>)<sub>6</sub>]. </p><p>Certain powdered lanthanides react with <a href="/wiki/Diphenylmercury" title="Diphenylmercury">diphenylmercury</a> in THF to yield octahedral complexes: </p> <dl><dd><dl><dd>2 Ln + 3 Ph<sub>2</sub>Hg + 6 THF → 2 LnPh<sub>3</sub>(THF)<sub>3</sub> + Hg (Ln = <a href="/wiki/Holmium" title="Holmium">Ho</a>, <a href="/wiki/Erbium" title="Erbium">Er</a>, <a href="/wiki/Thulium" title="Thulium">Tm</a>, <a href="/wiki/Lutetium" title="Lutetium">Lu</a>).</dd></dl></dd></dl> <div class="mw-heading mw-heading2"><h2 id="π-Bonded_complexes"><span id=".CF.80-Bonded_complexes"></span>π-Bonded complexes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organolanthanide_chemistry&action=edit&section=2" title="Edit section: π-Bonded complexes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Cyclopentadienyl_complex" title="Cyclopentadienyl complex">Cyclopentadienyl complexes</a>, including several <a href="/wiki/Lanthanocene" title="Lanthanocene">lanthanocenes</a>, are known for all lanthanides. All, barring tris(cyclopentadienyl)promethium(III) (Pm(Cp)<sub>3</sub>), can be produced by the following reaction scheme: </p> <dl><dd>3 Na[Cp] + MCl<sub>3 </sub> → M[Cp]<sub>3</sub> + 3 NaCl</dd></dl> <p>Pm(Cp)<sub>3</sub> can be produced by the following reaction: </p> <dl><dd>2 PmCl<sub>3</sub> + 3 Be[Cp]<sub>2</sub> → 3 BeCl<sub>2</sub> + 2 Pm[Cp]<sub>3</sub></dd></dl> <p>These compounds are of limited use and academic interest.<sup id="cite_ref-Zuckerman2009_1-0" class="reference"><a href="#cite_note-Zuckerman2009-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organolanthanide_chemistry&action=edit&section=3" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Organocerium_chemistry" title="Organocerium chemistry">Organocerium chemistry</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organolanthanide_chemistry&action=edit&section=4" 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-Zuckerman2009-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Zuckerman2009_1-0">^</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="CITEREFJ._J._Zuckerman2009" class="citation book cs1">J. J. Zuckerman (17 September 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=bWAfgilsYYMC"><i>Inorganic Reactions and Methods, The Formation of Bonds to Elements of Group IVB (C, Si, Ge, Sn, Pb)</i></a>. John Wiley & Sons. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-14547-0" title="Special:BookSources/978-0-470-14547-0"><bdi>978-0-470-14547-0</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">28 July</span> 2013</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Inorganic+Reactions+and+Methods%2C+The+Formation+of+Bonds+to+Elements+of+Group+IVB+%28C%2C+Si%2C+Ge%2C+Sn%2C+Pb%29&rft.pub=John+Wiley+%26+Sons&rft.date=2009-09-17&rft.isbn=978-0-470-14547-0&rft.au=J.+J.+Zuckerman&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DbWAfgilsYYMC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganolanthanide+chemistry" 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 dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline 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title="Carbon–hydrogen bond">CH</a> </td> <td colspan="1" style="border:none"> </td> <td colspan="11" style="border:none" rowspan="3"> </td> <td colspan="5" style="border:none"> </td> <td style="background-color:#FFE4E1">He </td></tr> <tr> <td style="background-color:#99bbff"><a href="/wiki/Organolithium_reagent" title="Organolithium reagent">CLi</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoberyllium_chemistry" title="Organoberyllium chemistry">CBe</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organoboron_chemistry" title="Organoboron chemistry">CB</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Carbon%E2%80%93carbon_bond" title="Carbon–carbon bond">CC</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Carbon%E2%80%93nitrogen_bond" title="Carbon–nitrogen bond">CN</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Carbon%E2%80%93oxygen_bond" title="Carbon–oxygen bond">CO</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organofluorine_chemistry" title="Organofluorine chemistry">CF</a> </td> <td style="background-color:#FFE4E1">Ne </td></tr> <tr> <td style="background-color:#98FF98"><a href="/wiki/Organosodium_chemistry" title="Organosodium chemistry">CNa</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organomagnesium_chemistry" class="mw-redirect" title="Organomagnesium chemistry">CMg</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoaluminium_chemistry" title="Organoaluminium chemistry">CAl</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organosilicon_chemistry" title="Organosilicon chemistry">CSi</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organophosphorus_chemistry" title="Organophosphorus chemistry">CP</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organosulfur_chemistry" title="Organosulfur chemistry">CS</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organochlorine_chemistry" title="Organochlorine chemistry">CCl</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoargon_chemistry" class="mw-redirect" title="Organoargon chemistry">CAr</a> </td></tr> <tr> <td style="background-color:#F0DC82"><a href="/wiki/Organopotassium_chemistry" class="mw-redirect" title="Organopotassium chemistry">CK</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organocalcium_chemistry" class="mw-redirect" title="Organocalcium chemistry">CCa</a> </td> <td> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoscandium_chemistry" title="Organoscandium chemistry">CSc</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organotitanium_chemistry" title="Organotitanium chemistry">CTi</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organovanadium_chemistry" title="Organovanadium chemistry">CV</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organochromium_chemistry" title="Organochromium chemistry">CCr</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organomanganese_chemistry" title="Organomanganese chemistry">CMn</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoiron_chemistry" title="Organoiron chemistry">CFe</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organocobalt_chemistry" title="Organocobalt chemistry">CCo</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organonickel_chemistry" title="Organonickel chemistry">CNi</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organocopper_chemistry" title="Organocopper chemistry">CCu</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organozinc_chemistry" title="Organozinc chemistry">CZn</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organogallium_chemistry" title="Organogallium chemistry">CGa</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organogermanium_chemistry" title="Organogermanium chemistry">CGe</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoarsenic_chemistry" title="Organoarsenic chemistry">CAs</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoselenium_chemistry" title="Organoselenium chemistry">CSe</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organobromine_chemistry" title="Organobromine chemistry">CBr</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organokrypton_chemistry" title="Organokrypton chemistry">CKr</a> </td></tr> <tr> <td style="background-color:#F0DC82"><a href="/wiki/Organorubidium_chemistry" class="mw-redirect" title="Organorubidium chemistry">CRb</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organostrontium_chemistry" class="mw-redirect" title="Organostrontium chemistry">CSr</a> </td> <td> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoyttrium_chemistry" title="Organoyttrium chemistry">CY</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organozirconium_chemistry" class="mw-redirect" title="Organozirconium chemistry">CZr</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoniobium_chemistry" title="Organoniobium chemistry">CNb</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organomolybdenum_chemistry" title="Organomolybdenum chemistry">CMo</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organotechnetium_chemistry" title="Organotechnetium chemistry">CTc</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoruthenium_chemistry" title="Organoruthenium chemistry">CRu</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organorhodium_chemistry" title="Organorhodium chemistry">CRh</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organopalladium_chemistry" title="Organopalladium chemistry">CPd</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organosilver_chemistry" title="Organosilver chemistry">CAg</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organocadmium_chemistry" title="Organocadmium chemistry">CCd</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoindium_chemistry" title="Organoindium chemistry">CIn</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organotin_chemistry" title="Organotin chemistry">CSn</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoantimony_chemistry" title="Organoantimony chemistry">CSb</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organotellurium_chemistry" title="Organotellurium chemistry">CTe</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organoiodine_chemistry" title="Organoiodine chemistry">CI</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoxenon_chemistry" title="Organoxenon chemistry">CXe</a> </td></tr> <tr> <td style="background-color:#F0DC82"><a href="/wiki/Organocesium_chemistry" class="mw-redirect" title="Organocesium chemistry">CCs</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organobarium_chemistry" class="mw-redirect" title="Organobarium chemistry">CBa</a> </td> <td style="text-align:center; vertical-align:middle; background:white"><span class="skin-invert-image" typeof="mw:File"><span><img alt="1 asterisk" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/16px-Asterisks_one.svg.png" decoding="async" width="16" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/24px-Asterisks_one.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/32px-Asterisks_one.svg.png 2x" data-file-width="106" data-file-height="98" /></span></span> </td> <td style="background-color:#F0DC82"><a class="mw-selflink selflink">CLu</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organohafnium_chemistry" class="mw-redirect" title="Organohafnium chemistry">CHf</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organotantalum_chemistry" title="Organotantalum chemistry">CTa</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organotungsten_chemistry" class="mw-redirect" title="Organotungsten chemistry">CW</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organorhenium_chemistry" title="Organorhenium chemistry">CRe</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoosmium_chemistry" class="mw-redirect" title="Organoosmium chemistry">COs</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoiridium_chemistry" title="Organoiridium chemistry">CIr</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoplatinum_chemistry" title="Organoplatinum chemistry">CPt</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organogold_chemistry" title="Organogold chemistry">CAu</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organomercury_chemistry" title="Organomercury chemistry">CHg</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organothallium_chemistry" title="Organothallium chemistry">CTl</a> </td> <td style="background-color:#98FF82"><a href="/wiki/Organolead_chemistry" title="Organolead chemistry">CPb</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organobismuth_chemistry" title="Organobismuth chemistry">CBi</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organopolonium_chemistry" title="Organopolonium chemistry">CPo</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoastatine_chemistry" title="Organoastatine chemistry">CAt</a> </td> <td style="background-color:#FFE4E1">Rn </td></tr> <tr style="background-color:#FFE4E1"> <td style="background-color:#FFE4E1">Fr </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoradium_chemistry" class="mw-redirect" title="Organoradium chemistry">CRa</a> </td> <td style="text-align:center; vertical-align:middle; background:white"><span class="skin-invert-image" typeof="mw:File"><span><img alt="2 asterisks" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/16px-Asterisks_two.svg.png" decoding="async" width="16" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/24px-Asterisks_two.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/32px-Asterisks_two.svg.png 2x" data-file-width="106" data-file-height="98" /></span></span> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">Lr</a> </td> <td>Rf </td> <td>Db </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoseaborgium_chemistry" class="mw-redirect" title="Organoseaborgium chemistry">CSg</a> </td> <td>Bh </td> <td>Hs </td> <td>Mt </td> <td>Ds </td> <td>Rg </td> <td>Cn </td> <td>Nh </td> <td>Fl </td> <td>Mc </td> <td>Lv </td> <td>Ts </td> <td>Og </td></tr> <tr> <td style="border:none; line-height:0.7em;">  </td></tr> <tr style="background-color:#F0DC82"> <td colspan="2" style="border:none; background-color:white"> </td> <td style="text-align:center; vertical-align:middle; background:white"><span class="skin-invert-image" typeof="mw:File"><span><img alt="1 asterisk" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/16px-Asterisks_one.svg.png" decoding="async" width="16" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/24px-Asterisks_one.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/32px-Asterisks_one.svg.png 2x" data-file-width="106" data-file-height="98" /></span></span> </td> <td style="background-color:#F0DC82"><a class="mw-selflink selflink">CLa</a> </td> <td><a href="/wiki/Organocerium_chemistry" title="Organocerium chemistry">CCe</a> </td> <td><a class="mw-selflink selflink">CPr</a> </td> <td><a class="mw-selflink selflink">CNd</a> </td> <td><a class="mw-selflink selflink">CPm</a> </td> <td><a class="mw-selflink selflink">CSm</a> </td> <td><a class="mw-selflink selflink">CEu</a> </td> <td><a class="mw-selflink selflink">CGd</a> </td> <td><a class="mw-selflink selflink">CTb</a> </td> <td><a class="mw-selflink selflink">CDy</a> </td> <td><a class="mw-selflink selflink">CHo</a> </td> <td><a class="mw-selflink selflink">CEr</a> </td> <td><a class="mw-selflink selflink">CTm</a> </td> <td><a class="mw-selflink selflink">CYb</a> </td></tr> <tr style="background-color:#FFE4E1"> <td colspan="2" style="border:none; background-color:white"> </td> <td style="text-align:center; vertical-align:middle; background:white;"><span class="skin-invert-image" typeof="mw:File"><span><img alt="2 asterisks" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/16px-Asterisks_two.svg.png" decoding="async" width="16" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/24px-Asterisks_two.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/32px-Asterisks_two.svg.png 2x" data-file-width="106" data-file-height="98" /></span></span> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">Ac</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organothorium_chemistry" title="Organothorium chemistry">CTh</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CPa</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organouranium_chemistry" title="Organouranium chemistry">CU</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoneptunium_chemistry" title="Organoneptunium chemistry">CNp</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CPu</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CAm</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CCm</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CBk</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CCf</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CEs</a> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">Fm</a> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">Md</a> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">No</a> </td></tr></tbody></table> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Legend</th><td class="navbox-list-with-group navbox-list navbox-even wikitable" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"><ul><li><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bonds</a> to carbon</li><li><span style="background:#99bbff; padding:3px;; display:inline-block;">Core organic chemistry</span></li><li><span style="background:#98FF98; padding:3px;; display:inline-block;">Many uses in chemistry</span></li><li><span style="background:#F0DC82; padding:3px;; display:inline-block;">Academic research, no widespread use</span></li><li><span style="background:#FFE4E1; padding:3px;; display:inline-block;">Bond unknown</span></li></ul></div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Branches_of_chemistry" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Branches_of_chemistry" title="Template:Branches of chemistry"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Branches_of_chemistry" title="Template talk:Branches of chemistry"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Branches_of_chemistry" title="Special:EditPage/Template:Branches of chemistry"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Branches_of_chemistry" style="font-size:114%;margin:0 4em">Branches of <a href="/wiki/Chemistry" title="Chemistry">chemistry</a></div></th></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/Glossary_of_chemical_formulae" title="Glossary of chemical formulae">Glossary of chemical formulae</a></li> <li><a href="/wiki/List_of_biomolecules" title="List of biomolecules">List of biomolecules</a></li> <li><a href="/wiki/List_of_inorganic_compounds" title="List of inorganic compounds">List of inorganic compounds</a></li> <li><a href="/wiki/Periodic_table" title="Periodic table">Periodic table</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Analytical_chemistry" title="Analytical chemistry">Analytical</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Instrumental_chemistry" title="Instrumental chemistry">Instrumental chemistry</a></li> <li><a href="/wiki/Electroanalytical_methods" title="Electroanalytical methods">Electroanalytical methods</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a> <ul><li><a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">IR</a></li> <li><a href="/wiki/Raman_spectroscopy" title="Raman spectroscopy">Raman</a></li> <li><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-Vis</a></li> <li><a href="/wiki/Nuclear_magnetic_resonance_spectroscopy" title="Nuclear magnetic resonance spectroscopy">NMR</a></li></ul></li> <li><a href="/wiki/Mass_spectrometry" title="Mass spectrometry">Mass spectrometry</a> <ul><li><a href="/wiki/Electron_ionization" title="Electron ionization">EI</a></li> <li><a href="/wiki/Inductively_coupled_plasma_mass_spectrometry" title="Inductively coupled plasma mass spectrometry">ICP</a></li> <li><a href="/wiki/Matrix-assisted_laser_desorption/ionization" title="Matrix-assisted laser desorption/ionization">MALDI</a></li></ul></li> <li><a href="/wiki/Separation_process" title="Separation process">Separation process</a></li> <li><a href="/wiki/Chromatography" title="Chromatography">Chromatography</a> <ul><li><a href="/wiki/Gas_chromatography" title="Gas chromatography">GC</a></li> <li><a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a></li></ul></li> <li><a href="/wiki/Crystallography" title="Crystallography">Crystallography</a></li> <li><a href="/wiki/Characterization_(materials_science)" title="Characterization (materials science)">Characterization</a></li> <li><a href="/wiki/Titration" title="Titration">Titration</a></li> <li><a href="/wiki/Wet_chemistry" title="Wet chemistry">Wet chemistry</a></li> <li><a href="/wiki/Calorimetry" title="Calorimetry">Calorimetry</a></li> <li><a href="/wiki/Elemental_analysis" title="Elemental analysis">Elemental analysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Theoretical_chemistry" title="Theoretical chemistry">Theoretical</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Quantum_chemistry" title="Quantum chemistry">Quantum chemistry</a></li> <li><a href="/wiki/Computational_chemistry" title="Computational chemistry">Computational chemistry</a> <ul><li><a href="/wiki/Mathematical_chemistry" title="Mathematical chemistry">Mathematical chemistry</a></li></ul></li> <li><a href="/wiki/Molecular_modelling" title="Molecular modelling">Molecular modelling</a></li> <li><a href="/wiki/Molecular_mechanics" title="Molecular mechanics">Molecular mechanics</a></li> <li><a href="/wiki/Molecular_dynamics" title="Molecular dynamics">Molecular dynamics</a></li> <li><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular geometry</a> <ul><li><a href="/wiki/VSEPR_theory" title="VSEPR theory">VSEPR theory</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Physical_chemistry" title="Physical chemistry">Physical</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electrochemistry" title="Electrochemistry">Electrochemistry</a> <ul><li><a href="/wiki/Spectroelectrochemistry" title="Spectroelectrochemistry">Spectroelectrochemistry</a></li> <li><a href="/wiki/Photoelectrochemistry" title="Photoelectrochemistry">Photoelectrochemistry</a></li></ul></li> <li><a href="/wiki/Thermochemistry" title="Thermochemistry">Thermochemistry</a></li> <li><a href="/wiki/Chemical_thermodynamics" title="Chemical thermodynamics">Chemical thermodynamics</a></li> <li><a href="/wiki/Surface_science" title="Surface science">Surface science</a></li> <li><a href="/wiki/Interface_and_colloid_science" title="Interface and colloid science">Interface and colloid science</a> <ul><li><a href="/wiki/Micromeritics" title="Micromeritics">Micromeritics</a></li></ul></li> <li><a href="/wiki/Cryochemistry" title="Cryochemistry">Cryochemistry</a></li> <li><a href="/wiki/Sonochemistry" title="Sonochemistry">Sonochemistry</a></li> <li><a href="/wiki/Structural_chemistry" title="Structural chemistry">Structural chemistry</a></li> <li><a href="/wiki/Chemical_physics" title="Chemical physics">Chemical physics</a> <ul><li><a href="/wiki/Molecular_physics" title="Molecular physics">Molecular physics</a></li></ul></li> <li><a href="/wiki/Femtochemistry" title="Femtochemistry">Femtochemistry</a></li> <li><a href="/wiki/Chemical_kinetics" title="Chemical kinetics">Chemical kinetics</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Photochemistry" title="Photochemistry">Photochemistry</a></li> <li><a href="/wiki/Spin_chemistry" title="Spin chemistry">Spin chemistry</a></li> <li><a href="/wiki/Microwave_chemistry" title="Microwave chemistry">Microwave chemistry</a></li> <li><a href="/wiki/Equilibrium_chemistry" title="Equilibrium chemistry">Equilibrium chemistry</a></li> <li><a href="/wiki/Mechanochemistry" title="Mechanochemistry">Mechanochemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">Inorganic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Coordination_complex" title="Coordination complex">Coordination chemistry</a></li> <li><a href="/wiki/Magnetochemistry" title="Magnetochemistry">Magnetochemistry</a></li> <li><a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">Organometallic chemistry</a> <ul><li><a class="mw-selflink selflink">Organolanthanide chemistry</a></li></ul></li> <li><a href="/wiki/Atom_cluster" class="mw-redirect" title="Atom cluster">Cluster chemistry</a></li> <li><a href="/wiki/Solid-state_chemistry" title="Solid-state chemistry">Solid-state chemistry</a></li> <li><a href="/wiki/Ceramic_chemistry" class="mw-redirect" title="Ceramic chemistry">Ceramic chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_chemistry" title="Organic chemistry">Organic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stereochemistry" title="Stereochemistry">Stereochemistry</a> <ul><li><a href="/wiki/Alkane_stereochemistry" class="mw-redirect" title="Alkane stereochemistry">Alkane stereochemistry</a></li></ul></li> <li><a href="/wiki/Physical_organic_chemistry" title="Physical organic chemistry">Physical organic chemistry</a></li> <li><a href="/wiki/Organic_reactions" class="mw-redirect" title="Organic reactions">Organic reactions</a></li> <li><a href="/wiki/Organic_synthesis" title="Organic synthesis">Organic synthesis</a></li> <li><a href="/wiki/Retrosynthetic_analysis" title="Retrosynthetic analysis">Retrosynthetic analysis</a></li> <li><a href="/wiki/Enantioselective_synthesis" title="Enantioselective synthesis">Enantioselective synthesis</a></li> <li><a href="/wiki/Total_synthesis" title="Total synthesis">Total synthesis</a> / <a href="/wiki/Semisynthesis" title="Semisynthesis">Semisynthesis</a></li> <li><a href="/wiki/Fullerene_chemistry" title="Fullerene chemistry">Fullerene chemistry</a></li> <li><a href="/wiki/Polymer_chemistry" title="Polymer chemistry">Polymer chemistry</a></li> <li><a href="/wiki/Petrochemistry" class="mw-redirect" title="Petrochemistry">Petrochemistry</a></li> <li><a href="/wiki/Dynamic_covalent_chemistry" title="Dynamic covalent chemistry">Dynamic covalent chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Biochemistry" title="Biochemistry">Biological</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Biochemistry" title="Biochemistry">Biochemistry</a> <ul><li><a href="/wiki/Molecular_biology" title="Molecular biology">Molecular biology</a></li> <li><a href="/wiki/Cell_biology" title="Cell biology">Cell biology</a></li></ul></li> <li><a href="/wiki/Chemical_biology" title="Chemical biology">Chemical biology</a> <ul><li><a href="/wiki/Bioorthogonal_chemistry" title="Bioorthogonal chemistry">Bioorthogonal chemistry</a></li></ul></li> <li><a href="/wiki/Medicinal_chemistry" title="Medicinal chemistry">Medicinal chemistry</a> <ul><li><a href="/wiki/Pharmacology" title="Pharmacology">Pharmacology</a></li></ul></li> <li><a href="/wiki/Clinical_chemistry" title="Clinical 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