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class="mw-page-title-main">Carbon–hydrogen bond</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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class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Enlla%C3%A7_C-H" title="Enllaç C-H – Catalan" lang="ca" hreflang="ca" data-title="Enllaç C-H" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Vazba_uhl%C3%ADk%E2%80%93vod%C3%ADk" title="Vazba uhlík–vodík – Czech" lang="cs" hreflang="cs" data-title="Vazba uhlík–vodík" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Kohlenstoff-Wasserstoff-Bindung" title="Kohlenstoff-Wasserstoff-Bindung – German" lang="de" hreflang="de" data-title="Kohlenstoff-Wasserstoff-Bindung" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%94%CE%B5%CF%83%CE%BC%CF%8C%CF%82_%CE%AC%CE%BD%CE%B8%CF%81%CE%B1%CE%BA%CE%B1_-_%CF%85%CE%B4%CF%81%CE%BF%CE%B3%CF%8C%CE%BD%CE%BF%CF%85" title="Δεσμός άνθρακα - υδρογόνου – Greek" lang="el" hreflang="el" data-title="Δεσμός άνθρακα - υδρογόνου" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Enlace_carbono-hidr%C3%B3geno" title="Enlace carbono-hidrógeno – Spanish" lang="es" hreflang="es" data-title="Enlace carbono-hidrógeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link 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<div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" 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">Covalent chemical bond between hydrogen and carbon atoms</div> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, the <b>carbon–hydrogen bond</b> (<b><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">C−H</span> bond</b>) is a <a href="/wiki/Chemical_bond" title="Chemical bond">chemical bond</a> between <a href="/wiki/Carbon" title="Carbon">carbon</a> and <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atoms that can be found in many <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a>.<sup id="cite_ref-March_1-0" class="reference"><a href="#cite_note-March-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> This bond is a <a href="/wiki/Covalent_bond" title="Covalent bond">covalent</a>, <a href="/wiki/Single_bond" title="Single bond">single bond</a>, meaning that carbon shares its outer <a href="/wiki/Valence_electron" title="Valence electron">valence electrons</a> with up to four hydrogens. This <a href="/wiki/Octet_rule" title="Octet rule">completes</a> both of their <a href="/wiki/Electron_shell" title="Electron shell">outer shells</a>, making them stable.<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><p>Carbon–hydrogen bonds have a <a href="/wiki/Bond_length" title="Bond length">bond length</a> of about 1.09 <a href="/wiki/%C3%85ngstr%C3%B6m" class="mw-redirect" title="Ångström">Å</a> (1.09 × 10<sup>−10</sup> m) and a <a href="/wiki/Bond_energy" title="Bond energy">bond energy</a> of about 413 <a href="/wiki/Joule" title="Joule">kJ</a>/<a href="/wiki/Mole_(unit)" title="Mole (unit)">mol</a> (see table below). Using <a href="/wiki/Electronegativities_of_the_elements_(data_page)" title="Electronegativities of the elements (data page)">Pauling's scale</a>—C (2.55) and H (2.2)—the <a href="/wiki/Electronegativity" title="Electronegativity">electronegativity</a> difference between these two atoms is 0.35. Because of this small difference in electronegativities, the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−H</span> bond is generally regarded as being <a href="/wiki/Non-polar" class="mw-redirect" title="Non-polar">non-polar</a>. In <a href="/wiki/Structural_formula" title="Structural formula">structural formulas</a> of molecules, the hydrogen atoms are often omitted. Compound classes consisting solely of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−H</span> bonds and <a href="/wiki/Carbon%E2%80%93carbon_bond" title="Carbon–carbon bond"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−C</span> bonds</a> are <a href="/wiki/Alkane" title="Alkane">alkanes</a>, <a href="/wiki/Alkene" title="Alkene">alkenes</a>, <a href="/wiki/Alkyne" title="Alkyne">alkynes</a>, and <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">aromatic hydrocarbons</a>. Collectively they are known as <a href="/wiki/Hydrocarbons" class="mw-redirect" title="Hydrocarbons">hydrocarbons</a>. </p><p>In October 2016, astronomers reported that the very basic chemical ingredients of <a href="/wiki/Life" title="Life">life</a>—the carbon–hydrogen molecule (CH, or <a href="/wiki/Methylidyne_radical" title="Methylidyne radical">methylidyne radical</a>), the carbon–hydrogen positive ion (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sup class="template-chem2-sup">+</sup></span>) and the carbon ion (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sup class="template-chem2-sup">+</sup></span>)—are created, in large part, using energy from the <a href="/wiki/Ultraviolet_light" class="mw-redirect" title="Ultraviolet light">ultraviolet light</a> of nearby <a href="/wiki/Star" title="Star">stars</a>, rather than in other ways, such as turbulent events related to <a href="/wiki/Supernovae" class="mw-redirect" title="Supernovae">supernovae</a> and <a href="/wiki/Young_star" class="mw-redirect" title="Young star">young stars</a>, as thought earlier.<sup id="cite_ref-NASA-20161012_3-0" class="reference"><a href="#cite_note-NASA-20161012-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Bond_length">Bond length</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbon%E2%80%93hydrogen_bond&action=edit&section=1" title="Edit section: Bond length"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The length of the carbonhydrogen bond varies slightly with the <a href="/wiki/Orbital_hybridization" class="mw-redirect" title="Orbital hybridization">hybridisation</a> of the carbon atom. A bond between a hydrogen atom and an sp<sup>2</sup> hybridised carbon atom is about 0.6% shorter than between hydrogen and sp<sup>3</sup> hybridised carbon. A bond between hydrogen and sp hybridised carbon is shorter still, about 3% shorter than sp<sup>3</sup> C-H. This trend is illustrated by the <a href="/wiki/Molecular_geometry" title="Molecular geometry">molecular geometry</a> of ethane, ethylene and acetylene.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2024)">citation needed</span></a></i>]</sup> </p> <table class="wikitable" style="text-align:center;"> <caption>Comparison of bond lengths in simple hydrocarbons<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> </caption> <tbody><tr> <th>Molecule </th> <td><b><a href="/wiki/Methane" title="Methane">Methane</a></b> </td> <td><b><a href="/wiki/Ethane" title="Ethane">Ethane</a></b> </td> <td><b><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></b> </td> <td><b><a href="/wiki/Acetylene" title="Acetylene">Acetylene</a></b> </td></tr> <tr> <th>Formula </th> <td>CH<sub>4</sub> </td> <td>C<sub>2</sub>H<sub>6</sub> </td> <td>C<sub>2</sub>H<sub>4</sub> </td> <td>C<sub>2</sub>H<sub>2</sub> </td></tr> <tr> <th>Class </th> <td><a href="/wiki/Alkane" title="Alkane">alkane</a> </td> <td><a href="/wiki/Alkane" title="Alkane">alkane</a> </td> <td><a href="/wiki/Alkene" title="Alkene">alkene</a> </td> <td><a href="/wiki/Alkyne" title="Alkyne">alkyne</a> </td></tr> <tr> <th>Structure </th> <td><span typeof="mw:File"><a href="/wiki/File:Methane-2D-dimensions.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Methane-2D-dimensions.svg/150px-Methane-2D-dimensions.svg.png" decoding="async" width="150" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Methane-2D-dimensions.svg/225px-Methane-2D-dimensions.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Methane-2D-dimensions.svg/300px-Methane-2D-dimensions.svg.png 2x" data-file-width="1000" data-file-height="750" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ethane-staggered-CRC-MW-dimensions-2D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Ethane-staggered-CRC-MW-dimensions-2D.png/170px-Ethane-staggered-CRC-MW-dimensions-2D.png" decoding="async" width="170" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Ethane-staggered-CRC-MW-dimensions-2D.png/255px-Ethane-staggered-CRC-MW-dimensions-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/68/Ethane-staggered-CRC-MW-dimensions-2D.png/340px-Ethane-staggered-CRC-MW-dimensions-2D.png 2x" data-file-width="1100" data-file-height="693" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ethylene-CRC-MW-dimensions-2D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/Ethylene-CRC-MW-dimensions-2D.png/160px-Ethylene-CRC-MW-dimensions-2D.png" decoding="async" width="160" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/Ethylene-CRC-MW-dimensions-2D.png/240px-Ethylene-CRC-MW-dimensions-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3b/Ethylene-CRC-MW-dimensions-2D.png/320px-Ethylene-CRC-MW-dimensions-2D.png 2x" data-file-width="1100" data-file-height="687" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Acetylene-CRC-IR-dimensions-2D.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Acetylene-CRC-IR-dimensions-2D.svg/150px-Acetylene-CRC-IR-dimensions-2D.svg.png" decoding="async" width="150" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Acetylene-CRC-IR-dimensions-2D.svg/225px-Acetylene-CRC-IR-dimensions-2D.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Acetylene-CRC-IR-dimensions-2D.svg/300px-Acetylene-CRC-IR-dimensions-2D.svg.png 2x" data-file-width="1100" data-file-height="700" /></a></span> </td></tr> <tr> <th>Hybridisation of carbon </th> <td>sp<sup>3</sup> </td> <td>sp<sup>3</sup> </td> <td>sp<sup>2</sup> </td> <td>sp </td></tr> <tr> <th>C-H bond length </th> <td><b>1.087 Å</b> </td> <td><b>1.094 Å</b> </td> <td><b>1.087 Å</b> </td> <td><b>1.060 Å</b> </td></tr> <tr> <th>Proportion of ethane C-H bond length </th> <td>99% </td> <td>100% </td> <td>99% </td> <td>97% </td></tr> <tr> <th>Structure determination method </th> <td><a href="/wiki/Rotational_spectroscopy" title="Rotational spectroscopy">microwave spectroscopy</a> </td> <td>microwave spectroscopy </td> <td>microwave spectroscopy </td> <td><a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">infrared spectroscopy</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbon%E2%80%93hydrogen_bond&action=edit&section=2" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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">Main article: <a href="/wiki/Carbon%E2%80%93hydrogen_bond_activation" title="Carbon–hydrogen bond activation">Carbon–hydrogen bond activation</a></div> <p>The C−H bond in general is very strong, so it is relatively unreactive. In several compound classes, collectively called <a href="/wiki/Carbon_acid" class="mw-redirect" title="Carbon acid">carbon acids</a>, the C−H bond can be sufficiently acidic for proton removal. Unactivated C−H bonds are found in alkanes and are not adjacent to a <a href="/wiki/Heteroatom" title="Heteroatom">heteroatom</a> (O, N, Si, etc.). Such bonds usually only participate in <a href="/wiki/Radical_substitution" title="Radical substitution">radical substitution</a>. Many enzymes are known, however, to effect these reactions.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Although the C−H bond is one of the strongest, it varies over 30% in magnitude for fairly stable organic compounds, even in the absence of <a href="/wiki/Heteroatoms" class="mw-redirect" title="Heteroatoms">heteroatoms</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable" style="text-align:center"> <tbody><tr> <th>Bond </th> <th>Hydrocarbon radical </th> <th>Molar Bond Dissociation Energy (kcal) </th> <th>Molar Bond Dissociation Energy (kJ) </th></tr> <tr> <td>CH<sub>3</sub>−H </td> <td><a href="/wiki/Methyl" class="mw-redirect" title="Methyl">Methyl</a> </td> <td>104 </td> <td>440 </td></tr> <tr> <td>C<sub>2</sub>H<sub>5</sub>−H </td> <td><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a> </td> <td>98 </td> <td>410 </td></tr> <tr> <td>(CH<sub>3</sub>)<sub>2</sub>HC−H </td> <td><a href="/wiki/Isopropyl" class="mw-redirect" title="Isopropyl">Isopropyl</a> </td> <td>95 </td> <td>400 </td></tr> <tr> <td>(CH<sub>3</sub>)<sub>3</sub>C−H </td> <td><a href="/wiki/Tert-Butyl" class="mw-redirect" title="Tert-Butyl">tert-Butyl</a> </td> <td>93 </td> <td>390 </td></tr> <tr> <td>CH<sub>2</sub>=CH−H </td> <td><a href="/wiki/Vinyl_group" title="Vinyl group">vinyl</a> </td> <td>112 </td> <td>470 </td></tr> <tr> <td>HC≡C−H </td> <td><a href="/wiki/Ethynyl" class="mw-redirect" title="Ethynyl">ethynyl</a> </td> <td>133 </td> <td>560 </td></tr> <tr> <td>C<sub>6</sub>H<sub>5</sub>−H </td> <td><a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a> </td> <td>110 </td> <td>460 </td></tr> <tr> <td>CH<sub>2</sub>=CHCH<sub>2</sub>−H </td> <td><a href="/wiki/Allyl" class="mw-redirect" title="Allyl">Allyl</a> </td> <td>88 </td> <td>370 </td></tr> <tr> <td>C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>−H </td> <td><a href="/wiki/Benzyl" class="mw-redirect" title="Benzyl">Benzyl</a> </td> <td>85 </td> <td>360 </td></tr> <tr> <td>OC<sub>4</sub>H<sub>7</sub>−H </td> <td><a href="/wiki/THF" class="mw-redirect" title="THF">tetrahydrofuranyl</a> </td> <td>92 </td> <td>380 </td></tr> <tr> <td>CH<sub>3</sub>C(O)CH<sub>2</sub>−H </td> <td><a href="/wiki/Acetone" title="Acetone">acetonyl</a> </td> <td>96 </td> <td>400 </td></tr> </tbody></table> <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=Carbon%E2%80%93hydrogen_bond&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/Carbon%E2%80%93carbon_bond" title="Carbon–carbon bond">Carbon–carbon bond</a></li> <li><a href="/wiki/Carbon%E2%80%93nitrogen_bond" title="Carbon–nitrogen bond">Carbon–nitrogen bond</a></li> <li><a href="/wiki/Carbon%E2%80%93oxygen_bond" title="Carbon–oxygen bond">Carbon–oxygen bond</a></li> <li><a href="/wiki/Carbon%E2%80%93fluorine_bond" title="Carbon–fluorine bond">Carbon–fluorine bond</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=Carbon%E2%80%93hydrogen_bond&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-March-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-March_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="CITEREFMarch,_Jerry1985" class="citation cs2"><a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (1985), <a rel="nofollow" class="external text" href="https://www.google.co.in/books/edition/_/ZKqWAQAACAAJ?hl=en"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition</i></a>, New York: Wiley, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471854722" title="Special:BookSources/9780471854722"><bdi>9780471854722</bdi></a>, <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/642506595">642506595</a></cite><span 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"Frontiers in enzymatic C-H-bond activation" Current Opinion in Chemical Biology 2009, vol. 13, page 51-7. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><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%2Fj.cbpa.2009.03.018">10.1016/j.cbpa.2009.03.018</a></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20160829213457/http://www.cem.msu.edu/~reusch/OrgPage/bndenrgy.htm">"Bond Energies"</a>. Organic Chemistry, Michigan State University. Archived from <a rel="nofollow" class="external text" href="http://www.cem.msu.edu/~reusch/OrgPage/bndenrgy.htm">the original</a> on 29 August 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Bond+Energies&rft.pub=Organic+Chemistry%2C+Michigan+State+University&rft_id=http%3A%2F%2Fwww.cem.msu.edu%2F~reusch%2FOrgPage%2Fbndenrgy.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbon%E2%80%93hydrogen+bond" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text">Yu-Ran Luo and Jin-Pei Cheng "Bond Dissociation Energies" in CRC Handbook of Chemistry and Physics, 96th Edition</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 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href="/wiki/Template:Molecules_detected_in_outer_space" title="Template:Molecules detected in outer space"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Molecules_detected_in_outer_space" title="Template talk:Molecules detected in outer space"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Molecules_detected_in_outer_space" title="Special:EditPage/Template:Molecules detected in outer space"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Molecules_detected_in_outer_space" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">Molecules detected in outer space</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecule" title="Molecule">Molecules</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diatomic_molecule" title="Diatomic molecule">Diatomic</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/Aluminium_monochloride" title="Aluminium monochloride">Aluminium monochloride</a></li> <li><a href="/wiki/Aluminium_monofluoride" title="Aluminium monofluoride">Aluminium monofluoride</a></li> <li><a href="/wiki/Aluminium(II)_oxide" title="Aluminium(II) oxide">Aluminium(II) oxide</a></li> <li><a href="/wiki/Argonium" title="Argonium">Argonium</a></li> <li><a href="/wiki/Carbon_cation" class="mw-redirect" title="Carbon cation">Carbon cation</a></li> <li><a href="/wiki/Carbon_monophosphide" title="Carbon monophosphide">Carbon monophosphide</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">Carbon monosulfide</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Cyano_radical" title="Cyano radical">Cyano radical</a></li> <li><a href="/wiki/Diatomic_carbon" title="Diatomic carbon">Diatomic carbon</a></li> <li><a href="/w/index.php?title=Fluoromethylidynium&action=edit&redlink=1" class="new" title="Fluoromethylidynium (page does not exist)">Fluoromethylidynium</a></li> <li><a href="/wiki/Helium_hydride_ion" title="Helium hydride ion">Helium hydride ion</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a></li> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">Hydrogen fluoride</a></li> <li><a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a> (molecular)</li> <li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">Hydroxyl radical</a></li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">Iron(II) oxide</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">Magnesium monohydride</a></li> <li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">Methylidyne radical</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> (molecular)</li> <li><a href="/wiki/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></li> <li><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> (molecular)</li> <li><a href="/wiki/Phosphorus_monoxide" title="Phosphorus monoxide">Phosphorus monoxide</a></li> <li><a href="/wiki/Phosphorus_mononitride" title="Phosphorus mononitride">Phosphorus mononitride</a></li> <li><a href="/wiki/Potassium_chloride" title="Potassium chloride">Potassium chloride</a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">Silicon carbide</a></li> <li><a href="/wiki/Silicon_monoxide" title="Silicon monoxide">Silicon monoxide</a></li> <li><a href="/wiki/Silicon_monosulfide" title="Silicon monosulfide">Silicon monosulfide</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Sodium chloride</a></li> <li><a href="/wiki/Sodium_iodide" title="Sodium iodide">Sodium iodide</a></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">Sulfanyl</a></li> <li><a href="/wiki/Sulfur_monoxide" title="Sulfur monoxide">Sulfur monoxide</a></li> <li><a href="/wiki/Titanium(II)_oxide" title="Titanium(II) oxide">Titanium(II) oxide</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/Nitrous_oxide" title="Nitrous oxide"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/60px-Nitrous-oxide-3D-balls.png" decoding="async" width="60" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/90px-Nitrous-oxide-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/120px-Nitrous-oxide-3D-balls.png 2x" data-file-width="1100" data-file-height="441" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Ethanol" title="Ethanol"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/60px-Ethanol-3D-balls.png" decoding="async" width="60" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/90px-Ethanol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/120px-Ethanol-3D-balls.png 2x" data-file-width="1100" data-file-height="754" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/60px-Buckminsterfullerene-perspective-3D-balls.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/90px-Buckminsterfullerene-perspective-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 2x" data-file-width="1056" data-file-height="1100" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triatomic_molecule" title="Triatomic molecule">Triatomic</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/Aluminium(I)_hydroxide" class="mw-redirect" title="Aluminium(I) hydroxide">Aluminium(I) hydroxide</a></li> <li><a href="/w/index.php?title=Aluminium_isocyanide&action=edit&redlink=1" class="new" title="Aluminium isocyanide (page does not exist)">Aluminium isocyanide</a></li> <li><a href="/wiki/Amino_radical" title="Amino radical">Amino radical</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide</a></li> <li><a href="/w/index.php?title=CCP_radical&action=edit&redlink=1" class="new" title="CCP radical (page does not exist)">CCP radical</a></li> <li><a href="/wiki/Halonium_ion" title="Halonium ion">Chloronium</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">Diazenylium</a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a></li> <li><a href="/w/index.php?title=Disilicon_carbide&action=edit&redlink=1" class="new" title="Disilicon carbide (page does not exist)">Disilicon carbide</a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">Ethynyl radical</a></li> <li><a href="/w/index.php?title=Formyl_radical&action=edit&redlink=1" class="new" title="Formyl radical (page does not exist)">Formyl radical</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (HCN)</li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a> (HNC)</li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">Hydroperoxyl</a></li> <li><a href="/w/index.php?title=Iron_cyanide&action=edit&redlink=1" class="new" title="Iron cyanide (page does not exist)">Iron cyanide</a></li> <li><a href="/w/index.php?title=Isoformyl&action=edit&redlink=1" class="new" title="Isoformyl (page does not exist)">Isoformyl</a></li> <li><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide">Magnesium cyanide</a></li> <li><a href="/w/index.php?title=Magnesium_isocyanide&action=edit&redlink=1" class="new" title="Magnesium isocyanide (page does not exist)">Magnesium isocyanide</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>H<sup>+</sup></a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl</a></li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">Sodium cyanide</a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">Sodium hydroxide</a></li> <li><a href="/w/index.php?title=Silicon_carbonitride&action=edit&redlink=1" class="new" title="Silicon carbonitride (page does not exist)">Silicon carbonitride</a></li> <li><a href="/w/index.php?title=C-Silicon_dicarbide&action=edit&redlink=1" class="new" title="C-Silicon dicarbide (page does not exist)">c-Silicon dicarbide</a></li> <li><a href="/w/index.php?title=SiNC&action=edit&redlink=1" class="new" title="SiNC (page does not exist)">SiNC</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/w/index.php?title=Thioformyl&action=edit&redlink=1" class="new" title="Thioformyl (page does not exist)">Thioformyl</a></li> <li><a href="/wiki/Thioxoethenylidene" title="Thioxoethenylidene">Thioxoethenylidene</a></li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a></li> <li><a href="/wiki/Tricarbon" title="Tricarbon">Tricarbon</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Four<br />atoms</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/Acetylene" title="Acetylene">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Cyanoethynyl</a></li> <li><a href="/wiki/Interstellar_formaldehyde" title="Interstellar formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Fulminic acid</a></li> <li><a href="/w/index.php?title=HCCN&action=edit&redlink=1" class="new" title="HCCN (page does not exist)">HCCN</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/w/index.php?title=Hydromagnesium_isocyanide&action=edit&redlink=1" class="new" title="Hydromagnesium isocyanide (page does not exist)">Hydromagnesium isocyanide</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Isothiocyanic acid</a></li> <li><a href="/w/index.php?title=Ketenyl&action=edit&redlink=1" class="new" title="Ketenyl (page does not exist)">Ketenyl</a></li> <li><a href="/w/index.php?title=Methylene_amidogen&action=edit&redlink=1" class="new" title="Methylene amidogen (page does not exist)">Methylene amidogen</a></li> <li><a href="/wiki/Methyl_cation" class="mw-redirect" title="Methyl cation">Methyl cation</a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">Methyl radical</a></li> <li><a href="/wiki/Propynylidyne" title="Propynylidyne">Propynylidyne</a></li> <li><a href="/w/index.php?title=Protonated_carbon_dioxide&action=edit&redlink=1" class="new" title="Protonated carbon dioxide (page does not exist)">Protonated carbon dioxide</a></li> <li><a href="/wiki/Protonated_hydrogen_cyanide" title="Protonated hydrogen cyanide">Protonated hydrogen cyanide</a></li> <li><a href="/w/index.php?title=Silicon_tricarbide&action=edit&redlink=1" class="new" title="Silicon tricarbide (page does not exist)">Silicon tricarbide</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Five<br />atoms</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/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Polyyne" title="Polyyne">Butadiynyl</a></li> <li><a href="/wiki/Carbodiimide" title="Carbodiimide">Carbodiimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li> <li><a href="/wiki/Cyanoacetylene" title="Cyanoacetylene">Cyanoacetylene</a></li> <li><a href="/w/index.php?title=Cyanoformaldehyde&action=edit&redlink=1" class="new" title="Cyanoformaldehyde (page does not exist)">Cyanoformaldehyde</a></li> <li><a href="/wiki/Cyanomethyl" title="Cyanomethyl">Cyanomethyl</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></li> <li><a href="/w/index.php?title=Isocyanoacetylene&action=edit&redlink=1" class="new" title="Isocyanoacetylene (page does not exist)">Isocyanoacetylene</a></li> <li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li> <li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy radical</a></li> <li><a href="/w/index.php?title=Methylenimine&action=edit&redlink=1" class="new" title="Methylenimine (page does not exist)">Methylenimine</a></li> <li><a href="/w/index.php?title=Propadienylidene&action=edit&redlink=1" class="new" title="Propadienylidene (page does not exist)">Propadienylidene</a></li> <li><a href="/w/index.php?title=Protonated_formaldehyde&action=edit&redlink=1" class="new" title="Protonated formaldehyde (page does not exist)">Protonated formaldehyde</a></li> <li><a href="/wiki/Silane" title="Silane">Silane</a></li> <li><a href="/w/index.php?title=Silicon-carbide_cluster&action=edit&redlink=1" class="new" title="Silicon-carbide cluster (page does not exist)">Silicon-carbide cluster</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Six<br />atoms</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/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/w/index.php?title=Cyanobutadiynyl_radical&action=edit&redlink=1" class="new" title="Cyanobutadiynyl radical (page does not exist)">Cyanobutadiynyl radical</a></li> <li><a href="/w/index.php?title=E-Cyanomethanimine&action=edit&redlink=1" class="new" title="E-Cyanomethanimine (page does not exist)">E-Cyanomethanimine</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Formamide" title="Formamide">Formamide</a></li> <li><a href="/w/index.php?title=HC4N&action=edit&redlink=1" class="new" title="HC4N (page does not exist)">HC<sub>4</sub>N</a></li> <li><a href="/wiki/Ketenimine" class="mw-redirect" title="Ketenimine">Ketenimine</a></li> <li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Pentynylidyne</a></li> <li><a href="/wiki/Propynal" class="mw-redirect" title="Propynal">Propynal</a></li> <li><a href="/w/index.php?title=Protonated_cyanoacetylene&action=edit&redlink=1" class="new" title="Protonated cyanoacetylene (page does not exist)">Protonated cyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Seven<br />atoms</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/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Acrylonitrile" title="Acrylonitrile">Acrylonitrile</a> <ul><li><a href="/wiki/Vinyl_cyanide" class="mw-redirect" title="Vinyl cyanide">Vinyl cyanide</a></li></ul></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodiacetylene</a></li> <li><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Hexatriynyl_radical" title="Hexatriynyl radical">Hexatriynyl radical</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">Vinyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Eight<br />atoms</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/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li> <li><a href="/w/index.php?title=Cyanoallene&action=edit&redlink=1" class="new" title="Cyanoallene (page does not exist)">Cyanoallene</a></li> <li><a href="/wiki/Ethanimine" title="Ethanimine">Ethanimine</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Hexapentaenylidene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Nine<br />atoms</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/Acetamide" title="Acetamide">Acetamide</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanohexatriyne</a></li> <li><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</a></li> <li><a href="/wiki/Octatetraynyl_radical" title="Octatetraynyl radical">Octatetraynyl radical</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Ten<br />atoms<br />or more</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/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Benzonitrile" title="Benzonitrile">Benzonitrile</a></li> <li><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene">Buckminsterfullerene</a> (C<sub>60</sub>, C<sub>60</sub><sup>+</sup>, fullerene, buckyball)</li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C<sub>70</sub> fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Methyl-cyano-diacetylene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyltriacetylene</a></li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li> <li><a href="/wiki/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li> <li><a href="/w/index.php?title=Heptatrienyl_radical&action=edit&redlink=1" class="new" title="Heptatrienyl radical (page does not exist)">Heptatrienyl radical</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deuterium" title="Deuterium">Deuterated</a><br />molecules</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/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Interstellar_formaldehyde#Interstellar_reactions" title="Interstellar formaldehyde">Formyl radical</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">Heavy water</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a></li> <li><a href="/wiki/Hydrogen_deuteride" title="Hydrogen deuteride">Hydrogen deuteride</a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Unconfirmed</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/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H<sub>2</sub>NCO<sup>+</sup></a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene cation</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Silylidyne" title="Silylidyne">Silylidyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#See_also" title="List of interstellar and circumstellar molecules">Related</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/Abiogenesis" title="Abiogenesis">Abiogenesis</a></li> <li><a href="/wiki/Astrobiology" title="Astrobiology">Astrobiology</a></li> <li><a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></li> <li><a href="/wiki/Atomic_and_molecular_astrophysics" title="Atomic and molecular astrophysics">Atomic and molecular astrophysics</a></li> <li><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></li> <li><a href="/wiki/Circumstellar_dust" title="Circumstellar dust">Circumstellar dust</a></li> <li><a href="/wiki/Circumstellar_envelope" title="Circumstellar envelope">Circumstellar envelope</a></li> <li><a href="/wiki/Cosmic_dust" title="Cosmic dust">Cosmic dust</a></li> <li><a href="/wiki/Cosmic_ray" title="Cosmic ray">Cosmic ray</a></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a></li> <li><a href="/wiki/Diffuse_interstellar_band" class="mw-redirect" title="Diffuse interstellar band">Diffuse interstellar band</a></li> <li><a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">Earliest known life forms</a></li> <li><a href="/wiki/Extraterrestrial_life" title="Extraterrestrial life">Extraterrestrial life</a></li> <li><a href="/wiki/Extraterrestrial_liquid_water" title="Extraterrestrial liquid water">Extraterrestrial liquid water</a></li> <li><a href="/wiki/Forbidden_mechanism" title="Forbidden mechanism">Forbidden mechanism</a></li> <li><a href="/wiki/Homochirality" title="Homochirality">Homochirality</a></li> <li><a href="/wiki/Intergalactic_dust" title="Intergalactic dust">Intergalactic dust</a></li> <li><a href="/wiki/Interplanetary_medium" title="Interplanetary medium">Interplanetary medium</a></li> <li><a href="/wiki/Interstellar_medium" title="Interstellar medium">Interstellar medium</a></li> <li><a href="/wiki/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Iron%E2%80%93sulfur_world_theory" class="mw-redirect" title="Iron–sulfur world theory">Iron–sulfur world theory</a></li> <li><a href="/wiki/Kerogen" title="Kerogen">Kerogen</a></li> <li><a href="/wiki/Molecules_in_stars" title="Molecules in stars">Molecules in stars</a></li> <li><a href="/wiki/Nexus_for_Exoplanet_System_Science" title="Nexus for Exoplanet System Science">Nexus for Exoplanet System Science</a></li> <li><a href="/wiki/Organic_compound" title="Organic compound">Organic compound</a></li> <li><a href="/wiki/Outer_space" title="Outer space">Outer space</a></li> <li><a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a></li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/RNA_world_hypothesis" class="mw-redirect" title="RNA world hypothesis">RNA world hypothesis</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Tholin" title="Tholin">Tholin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight: bold;"><div> <ul><li><b><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Astrochemistry" title="Category:Astrochemistry">Category:Astrochemistry</a></b></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/16px-Earth-moon.jpg" decoding="async" width="16" height="13" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/24px-Earth-moon.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/32px-Earth-moon.jpg 2x" data-file-width="3000" data-file-height="2400" /></span></span> </span><a href="/wiki/Portal:Outer_space" title="Portal:Outer space">Outer space portal</a></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/16px-Crab_Nebula.jpg" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/24px-Crab_Nebula.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/32px-Crab_Nebula.jpg 2x" data-file-width="3864" data-file-height="3864" /></span></span> </span><a href="/wiki/Portal:Astronomy" title="Portal:Astronomy">Astronomy portal</a></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/16px-Papapishu-Lab-icon-6.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/24px-Papapishu-Lab-icon-6.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/32px-Papapishu-Lab-icon-6.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span> </span><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Chemistry portal</a></li></ul> </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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Compounds_of_carbon_with_other_elements_in_the_periodic_table" style="padding:3px"><table class="nowraplinks 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:ChemicalBondsToCarbon" title="Template:ChemicalBondsToCarbon"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:ChemicalBondsToCarbon" title="Template talk:ChemicalBondsToCarbon"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:ChemicalBondsToCarbon" title="Special:EditPage/Template:ChemicalBondsToCarbon"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Compounds_of_carbon_with_other_elements_in_the_periodic_table" style="font-size:114%;margin:0 4em">Compounds of <a href="/wiki/Carbon" title="Carbon">carbon</a> with other elements in the periodic table</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd wikitable" style="width:100%;padding:0"><div style="padding:0 0.25em"> <table cellpadding="3" style="margin:0 auto"> <tbody><tr> <td style="background-color:#99bbff"><a class="mw-selflink selflink">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 href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">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 href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CLa</a> </td> <td><a href="/wiki/Organocerium_chemistry" title="Organocerium chemistry">CCe</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CPr</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CNd</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CPm</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CSm</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CEu</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CGd</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CTb</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CDy</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CHo</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CEr</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CTm</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">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><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Carbon–hydrogen_bond&oldid=1248856605">https://en.wikipedia.org/w/index.php?title=Carbon–hydrogen_bond&oldid=1248856605</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Organic_chemistry" title="Category:Organic chemistry">Organic chemistry</a></li><li><a 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