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Available in 10 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-10" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">10 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Karbyny" title="Karbyny – Czech" lang="cs" hreflang="cs" data-title="Karbyny" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Carbino" title="Carbino – Spanish" lang="es" hreflang="es" data-title="Carbino" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D8%B1%D8%A8%DB%8C%D9%86" title="کربین – Persian" lang="fa" hreflang="fa" data-title="کربین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Carbino" title="Carbino – Galician" lang="gl" hreflang="gl" data-title="Carbino" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Carbino" title="Carbino – Italian" lang="it" hreflang="it" data-title="Carbino" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Karbin" title="Karbin – Hungarian" lang="hu" hreflang="hu" data-title="Karbin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Carbino" title="Carbino – Portuguese" lang="pt" hreflang="pt" data-title="Carbino" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Karbyyni" title="Karbyyni – Finnish" lang="fi" hreflang="fi" data-title="Karbyyni" data-language-autonym="Suomi" data-language-local-name="Finnish" 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data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic molecule containing a neutral carbon atom with 3 unpaired valence electrons</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the chemical compounds with a –C<sup>3•</sup> group. For the allotrope of carbon containing consecutive alkyne units, see <a href="/wiki/Linear_acetylenic_carbon" title="Linear acetylenic carbon">linear acetylenic carbon</a>. For other uses, see <a href="/wiki/Carbyne_(disambiguation)" class="mw-disambig" title="Carbyne (disambiguation)">Carbyne (disambiguation)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Carbine" title="Carbine">carbine</a>, <a href="/wiki/Carbene" title="Carbene">carbene</a>, or <a href="/wiki/Carbones" title="Carbones">carbone</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1273380762/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner span:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent) img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner span:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent) img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:208px;max-width:208px"><div class="trow"><div class="tsingle" style="width:102px;max-width:102px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Carbyne_doublet.svg" class="mw-file-description"><img alt="carbyne doublet configuration" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Carbyne_doublet.svg/100px-Carbyne_doublet.svg.png" decoding="async" width="100" height="52" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Carbyne_doublet.svg/150px-Carbyne_doublet.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/54/Carbyne_doublet.svg/200px-Carbyne_doublet.svg.png 2x" data-file-width="296" data-file-height="153" /></a></span></div><div class="thumbcaption">doublet (1 radical, 1 pair, 1 vacant orbital)</div></div><div class="tsingle" style="width:102px;max-width:102px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Carbyne_quartet.svg" class="mw-file-description"><img alt="carbyne quartet configuration" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Carbyne_quartet.svg/100px-Carbyne_quartet.svg.png" decoding="async" width="100" height="66" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Carbyne_quartet.svg/150px-Carbyne_quartet.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Carbyne_quartet.svg/200px-Carbyne_quartet.svg.png 2x" data-file-width="296" data-file-height="194" /></a></span></div><div class="thumbcaption">quartet (3 radicals)</div></div></div></div></div> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>carbyne</b> is a general term for any <a href="/wiki/Chemical_compound" title="Chemical compound">compound</a> whose <a href="/wiki/Molecular_structure" class="mw-redirect" title="Molecular structure">structure</a> consists of an <a href="/wiki/Electric_charge" title="Electric charge">electrically neutral</a> <a href="/wiki/Carbon" title="Carbon">carbon</a> atom connected by a <a href="/wiki/Single_bond" title="Single bond">single covalent bond</a> and has three non-bonded electrons.<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> The carbon atom has either one or three unpaired <a href="/wiki/Electron" title="Electron">electrons</a>, depending on its <a href="/wiki/Excited_state" title="Excited state">excitation state</a>; making it a <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a>. The <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> can be written <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">R−C·</span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C<sup class="template-chem2-sup">3·</sup></span> (also written as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">⫶C−R</span>), or just CH. </p><p>Carbynes can be seen as derivatives of the simplest such compound, the <a href="/wiki/Methylidyne_radical" title="Methylidyne radical">methylidyne radical</a> or <a href="/wiki/Substitution_(chemistry)" class="mw-redirect" title="Substitution (chemistry)">unsubstituted</a> carbyne <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H−C·</span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H−C<sup class="template-chem2-sup">3·</sup></span>, in which the functional group is a <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atom. </p><p>Reported for the first time back in 1967 by Kasatochkin, carbyne is an infinite sp1 hybridized long linear chain of carbon, where each link is just a single carbon atom.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Electronic_configuration">Electronic configuration</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbyne&action=edit&section=1" title="Edit section: Electronic configuration"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbyne molecules are generally found to be in electronic <a href="/wiki/Doublet_state" title="Doublet state">doublet states</a>: the non-bonding electrons on carbon are arranged as one <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a> (unpaired electron) and one electron pair, leaving a vacant <a href="/wiki/Atomic_orbital" title="Atomic orbital">atomic orbital</a>, rather than being a triradical (the <a href="/w/index.php?title=Quartet_state&action=edit&redlink=1" class="new" title="Quartet state (page does not exist)">quartet state</a>). The simplest case is the CH radical, which has an <a href="/wiki/Electron_configuration" title="Electron configuration">electron configuration</a> <span class="nowrap">1σ<sup>2</sup> 2σ<sup>2</sup> 3σ<sup>2</sup> 1π</span>.<sup id="cite_ref-Ruzsicska_3-0" class="reference"><a href="#cite_note-Ruzsicska-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Here the 1σ <a href="/wiki/Molecular_orbital" title="Molecular orbital">molecular orbital</a> is essentially the carbon 1s atomic orbital, and the 2σ is the C–H bonding orbital formed by <a href="/wiki/Orbital_overlap" title="Orbital overlap">overlap</a> of a carbon sp <a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">hybrid orbital</a> with the hydrogen 1s orbital. The 3σ is a carbon <a href="/wiki/Non-bonding_orbital" title="Non-bonding orbital">non-bonding orbital</a> pointing along the C–H axis away from the hydrogen, while there are two non-bonding 1π orbitals perpendicular to the C–H axis. However the 3σ is an sp hybrid which has lower energy than the 1π orbital which is pure p, so the 3σ is filled before the 1π. The CH radical is in fact <a href="/wiki/Isoelectronic" class="mw-redirect" title="Isoelectronic">isoelectronic</a> with the nitrogen atom which does have three unpaired electrons in accordance with <a href="/wiki/Hund%27s_rule_of_maximum_multiplicity" title="Hund's rule of maximum multiplicity">Hund's rule of maximum multiplicity</a>. However the nitrogen atom has three <a href="/wiki/Degenerate_energy_levels" title="Degenerate energy levels">degenerate</a> p orbitals, in contrast to the CH radical where hybridization of one orbital (the 3σ) leads to an energy difference. </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbyne&action=edit&section=2" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A carbyne can occur as a short-lived <a href="/wiki/Reactive_intermediate" title="Reactive intermediate">reactive intermediate</a>. For instance, <a href="/wiki/Fluoromethylidyne" title="Fluoromethylidyne">fluoromethylidyne</a> (CF) can be detected in the gas phase by spectroscopy as an intermediate in the <a href="/wiki/Flash_photolysis" title="Flash photolysis">flash photolysis</a> of <a href="/wiki/Dibromofluoromethane" title="Dibromofluoromethane">CHFBr<sub>2</sub></a>.<sup id="cite_ref-Ruzsicska_3-1" class="reference"><a href="#cite_note-Ruzsicska-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Carbynes can act as trivalent <a href="/wiki/Ligand" title="Ligand">ligands</a> in <a href="/wiki/Transition_metal_carbyne_complex" title="Transition metal carbyne complex">complexes with transition metals</a>, in which they are connected to a <a href="/wiki/Metal" title="Metal">metal</a> by the three non-bonded electrons in the –C<sup>3•</sup> group. Examples of such <a href="/wiki/Coordination_compound" class="mw-redirect" title="Coordination compound">coordination compounds</a> are <span class="chemf nowrap">Cl(CO)<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span>W≡C-CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>,<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> <a href="/wiki/Tungsten" title="Tungsten">W</a><a href="/wiki/Bromine" title="Bromine">Br</a>(<a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">CO</a>)<sub>2</sub>(<a href="/wiki/2,2%27-bipyridine" class="mw-redirect" title="2,2'-bipyridine">2,2'-bipyridine</a>)≡<a href="/wiki/Carbon" title="Carbon">C</a>-<a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a> and WBr(CO)<sub>2</sub>(<a href="/wiki/Triphenylphosphine" title="Triphenylphosphine">PPh<sub>3</sub></a>)<sub>2</sub>≡C-NR<sub>2</sub>.<sup id="cite_ref-jaeg_5-0" class="reference"><a href="#cite_note-jaeg-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Such a compound can be obtained by the reaction of <a href="/wiki/Tungsten_hexacarbonyl" title="Tungsten hexacarbonyl">tungsten hexacarbonyl</a> W(CO)<sub>6</sub> with <a href="/wiki/Lithium_diisopropylamide" title="Lithium diisopropylamide">lithium diisopropylamide</a> to form (<a href="/wiki/Isopropyl" class="mw-redirect" title="Isopropyl"><sup>i</sup>Pr</a><sub>2</sub>N)(OLi)C=W(CO)<sub>5</sub>. This salt is then oxidized with either <a href="/w/index.php?title=Oxalyl_bromide&action=edit&redlink=1" class="new" title="Oxalyl bromide (page does not exist)">oxalyl bromide</a> or <a href="/wiki/Triphenylphosphine_dibromide" class="mw-redirect" title="Triphenylphosphine dibromide">triphenylphosphine dibromide</a>, followed by addition of <a href="/wiki/Triphenylphosphine" title="Triphenylphosphine">triphenylphosphine</a>. Another method is to treat a methoxy metal <a href="/wiki/Carbene" title="Carbene">carbene</a> with a <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a>.<sup id="cite_ref-jaeg_5-1" class="reference"><a href="#cite_note-jaeg-5"><span class="cite-bracket">[</span>5<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=Carbyne&action=edit&section=3" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Carbyne" class="extiw" title="commons:Category:Carbyne">Carbyne</a></span>.</div></div> </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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/C00854.html">carbynes</a>". <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.C00854">10.1351/goldbook.C00854</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKASATOCHKINVVYPAM1973" class="citation journal cs1">KASATOCHKIN, VI; VV, KORSHAK; YP, KUDRYAVTSEV; AM, SLADKOV; IE, STERENBERG (1973). <a rel="nofollow" class="external text" href="https://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=PASCAL7316105892">"ON CRYSTALLINE STRUCTURE OF CARBYNE"</a>. <i>On Crystalline Structure of Carbyne</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=On+Crystalline+Structure+of+Carbyne&rft.atitle=ON+CRYSTALLINE+STRUCTURE+OF+CARBYNE&rft.date=1973&rft.aulast=KASATOCHKIN&rft.aufirst=VI&rft.au=VV%2C+KORSHAK&rft.au=YP%2C+KUDRYAVTSEV&rft.au=AM%2C+SLADKOV&rft.au=IE%2C+STERENBERG&rft_id=https%3A%2F%2Fpascal-francis.inist.fr%2Fvibad%2Findex.php%3Faction%3DgetRecordDetail%26idt%3DPASCAL7316105892&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbyne" class="Z3988"></span></span> </li> <li id="cite_note-Ruzsicska-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ruzsicska_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ruzsicska_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRuzsicska,_B._P.Jodhan,_A.Choi,_H._K._J.Strausz,_O._P.1983" class="citation journal cs1">Ruzsicska, B. P.; Jodhan, A.; Choi, H. K. J.; <a href="/wiki/Otto_P._Strausz" title="Otto P. Strausz">Strausz, O. P.</a>; Bell, T. N. (1983). "Chemistry of carbynes: reaction of CF, CCl, and CBr with alkenes". <i>J. Am. Chem. Soc</i>. <b>105</b> (8): <span class="nowrap">2489–</span>2490. <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%2Fja00346a072">10.1021/ja00346a072</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Chemistry+of+carbynes%3A+reaction+of+CF%2C+CCl%2C+and+CBr+with+alkenes&rft.volume=105&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2489-%3C%2Fspan%3E2490&rft.date=1983&rft_id=info%3Adoi%2F10.1021%2Fja00346a072&rft.au=Ruzsicska%2C+B.+P.&rft.au=Jodhan%2C+A.&rft.au=Choi%2C+H.+K.+J.&rft.au=Strausz%2C+O.+P.&rft.au=Bell%2C+T.+N.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbyne" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFischerKreisKreiterMüller1973" class="citation journal cs1">Fischer, Ernst Otto; Kreis, Gerhard; Kreiter, Cornelius G.; Müller, Jörn; Huttner, Gottfried; Lorenz, Hans (1973). "<i>trans</i>-Halogeno[alkyl(aryl)carbyne]tetracarbonyl Complexes of Chromium, Molybdenum, and Tungsten—A New Class of Compounds Having a Transition Metal-Carbon Triple Bond". <i>Angewandte Chemie International Edition in English</i>. <b>12</b> (7): <span class="nowrap">564–</span>565. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.197305641">10.1002/anie.197305641</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition+in+English&rft.atitle=trans-Halogeno%5Balkyl%28aryl%29carbyne%5Dtetracarbonyl+Complexes+of+Chromium%2C+Molybdenum%2C+and+Tungsten%E2%80%94A+New+Class+of+Compounds+Having+a+Transition+Metal-Carbon+Triple+Bond&rft.volume=12&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E564-%3C%2Fspan%3E565&rft.date=1973&rft_id=info%3Adoi%2F10.1002%2Fanie.197305641&rft.aulast=Fischer&rft.aufirst=Ernst+Otto&rft.au=Kreis%2C+Gerhard&rft.au=Kreiter%2C+Cornelius+G.&rft.au=M%C3%BCller%2C+J%C3%B6rn&rft.au=Huttner%2C+Gottfried&rft.au=Lorenz%2C+Hans&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbyne" class="Z3988"></span></span> </li> <li id="cite_note-jaeg-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-jaeg_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-jaeg_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJaeger,_M.Stumpf,_R.Troll,_C.Fischer,_H.2000" class="citation journal cs1">Jaeger, M.; Stumpf, R.; Troll, C.; Fischer, H. 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Commun.</i> (11): <span class="nowrap">931–</span>932. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FB002228O">10.1039/B002228O</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Commun.&rft.atitle=Novel+hepta-coordinated+molybdenum%28II%29+and+tungsten%28II%29+carbene+complexes+by+oxidative+decarbonylation+of+Mo%280%29+and+W%280%29+carbene+complexes&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E931-%3C%2Fspan%3E932&rft.date=2000&rft_id=info%3Adoi%2F10.1039%2FB002228O&rft.au=Jaeger%2C+M.&rft.au=Stumpf%2C+R.&rft.au=Troll%2C+C.&rft.au=Fischer%2C+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbyne" 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 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