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Carbon suboxide - Wikipedia

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class="firstHeading mw-first-heading"><span class="mw-page-title-main">Carbon suboxide</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. Available in 29 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-29" 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">29 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Koolstofsuboksied" title="Koolstofsuboksied – Afrikaans" lang="af" hreflang="af" data-title="Koolstofsuboksied" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AA%D8%AD%D8%AA_%D8%A3%D9%83%D8%B3%D9%8A%D8%AF_%D8%A7%D9%84%D9%83%D8%B1%D8%A8%D9%88%D9%86" title="تحت أكسيد الكربون – Arabic" lang="ar" hreflang="ar" data-title="تحت أكسيد الكربون" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%DA%A9%D8%B1%D8%A8%D9%88%D9%86_%D8%B3%D8%A7%D8%A8%D9%88%DA%A9%D8%B3%DB%8C%D8%AF" title="کربون سابوکسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="کربون سابوکسید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Suboxid_uhl%C3%ADku" title="Suboxid uhlíku – Czech" lang="cs" hreflang="cs" data-title="Suboxid uhlíku" 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/Kohlenstoffsuboxid" title="Kohlenstoffsuboxid – German" lang="de" hreflang="de" data-title="Kohlenstoffsuboxid" 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%A5%CF%80%CE%BF%CE%BE%CE%B5%CE%AF%CE%B4%CE%B9%CE%BF_%CF%84%CE%BF%CF%85_%CE%AC%CE%BD%CE%B8%CF%81%CE%B1%CE%BA%CE%B1" title="Υποξείδιο του άνθρακα – Greek" lang="el" hreflang="el" data-title="Υποξείδιο του άνθρακα" 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/Di%C3%B3xido_de_tricarbono" title="Dióxido de tricarbono – Spanish" lang="es" hreflang="es" data-title="Dióxido de tricarbono" 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%D9%86_%D8%B3%D8%A7%D8%A8%D9%88%DA%A9%D8%B3%DB%8C%D8%AF" title="کربن سابوکسید – Persian" lang="fa" hreflang="fa" data-title="کربن سابوکسید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Suboxyde_de_carbone" title="Suboxyde de carbone – French" lang="fr" hreflang="fr" data-title="Suboxyde de carbone" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%EC%82%B0%ED%99%94_%ED%83%84%EC%86%8C" title="아산화 탄소 – Korean" lang="ko" hreflang="ko" data-title="아산화 탄소" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Karbon_suboksida" title="Karbon suboksida – Indonesian" lang="id" hreflang="id" data-title="Karbon suboksida" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Subossido_di_carbonio" title="Subossido di carbonio – Italian" lang="it" hreflang="it" data-title="Subossido di carbonio" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Oglek%C4%BCa_suboks%C4%ABds" title="Oglekļa suboksīds – Latvian" lang="lv" hreflang="lv" data-title="Oglekļa suboksīds" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Sz%C3%A9n-szuboxid" title="Szén-szuboxid – Hungarian" lang="hu" hreflang="hu" data-title="Szén-szuboxid" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Karbon_suboksida" title="Karbon suboksida – Malay" lang="ms" hreflang="ms" data-title="Karbon suboksida" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Koolstofsuboxide" title="Koolstofsuboxide – Dutch" lang="nl" hreflang="nl" data-title="Koolstofsuboxide" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E4%BA%9C%E9%85%B8%E5%8C%96%E7%82%AD%E7%B4%A0" title="亜酸化炭素 – Japanese" lang="ja" hreflang="ja" data-title="亜酸化炭素" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Podtlenek_w%C4%99gla" title="Podtlenek węgla – Polish" lang="pl" hreflang="pl" data-title="Podtlenek węgla" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Suboxid_de_carbon" title="Suboxid de carbon – Romanian" lang="ro" hreflang="ro" data-title="Suboxid de carbon" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%94%D0%B8%D0%BE%D0%BA%D1%81%D0%B8%D0%B4_%D1%82%D1%80%D0%B8%D1%83%D0%B3%D0%BB%D0%B5%D1%80%D0%BE%D0%B4%D0%B0" title="Диоксид триуглерода – Russian" lang="ru" hreflang="ru" data-title="Диоксид триуглерода" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Carbon_suboxide" title="Carbon suboxide – Simple English" lang="en-simple" hreflang="en-simple" data-title="Carbon suboxide" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A3%D0%B3%D1%99%D0%B5%D0%BD%D0%B8%D0%BA_%D1%81%D1%83%D0%B1%D0%BE%D0%BA%D1%81%D0%B8%D0%B4" title="Угљеник субоксид – Serbian" lang="sr" hreflang="sr" data-title="Угљеник субоксид" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Ugljenik_suboksid" title="Ugljenik suboksid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ugljenik suboksid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Hiilisuboksidi" title="Hiilisuboksidi – Finnish" lang="fi" hreflang="fi" data-title="Hiilisuboksidi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%84%E0%B8%B2%E0%B8%A3%E0%B9%8C%E0%B8%9A%E0%B8%AD%E0%B8%99%E0%B8%8B%E0%B8%B1%E0%B8%9A%E0%B8%AD%E0%B8%AD%E0%B8%81%E0%B9%84%E0%B8%8B%E0%B8%94%E0%B9%8C" title="คาร์บอนซับออกไซด์ – Thai" lang="th" hreflang="th" data-title="คาร์บอนซับออกไซด์" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%94%D1%96%D0%BE%D0%BA%D1%81%D0%B8%D0%B4_%D1%82%D1%80%D0%B8%D0%B2%D1%83%D0%B3%D0%BB%D0%B5%D1%86%D1%8E" title="Діоксид тривуглецю – Ukrainian" lang="uk" hreflang="uk" data-title="Діоксид тривуглецю" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Carbon_suboxide" title="Carbon suboxide – Vietnamese" lang="vi" hreflang="vi" data-title="Carbon suboxide" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E4%BA%8C%E6%B0%A7%E5%8C%96%E4%B8%89%E7%A2%B3" title="二氧化三碳 – Cantonese" lang="yue" hreflang="yue" data-title="二氧化三碳" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%BA%8C%E6%B0%A7%E5%8C%96%E4%B8%89%E7%A2%B3" title="二氧化三碳 – Chinese" lang="zh" hreflang="zh" data-title="二氧化三碳" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q411352#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div 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#a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Carbon suboxide </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Carbon-suboxide-2D-dimensions.svg" class="mw-file-description" title="Stick model of carbon suboxide"><img alt="Stick model of carbon suboxide" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/Carbon-suboxide-2D-dimensions.svg/200px-Carbon-suboxide-2D-dimensions.svg.png" decoding="async" width="200" height="72" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/Carbon-suboxide-2D-dimensions.svg/300px-Carbon-suboxide-2D-dimensions.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3b/Carbon-suboxide-2D-dimensions.svg/400px-Carbon-suboxide-2D-dimensions.svg.png 2x" data-file-width="440" data-file-height="158" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Carbon-suboxide-3D-vdW.png" class="mw-file-description" title="Spacefill model of carbon suboxide"><img alt="Spacefill model of carbon suboxide" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Carbon-suboxide-3D-vdW.png/200px-Carbon-suboxide-3D-vdW.png" decoding="async" width="200" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Carbon-suboxide-3D-vdW.png/300px-Carbon-suboxide-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/Carbon-suboxide-3D-vdW.png/400px-Carbon-suboxide-3D-vdW.png 2x" data-file-width="1100" data-file-height="553" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Propa-1,2-diene-1,3-dione</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><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="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=504-64-3">504-64-3</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%3DC%3DC%3DO">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=30086">CHEBI:30086</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.120106.html">120106</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&amp;term=Carbon+suboxide">Carbon+suboxide</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/136332">136332</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/9M2M4H5WEJ">9M2M4H5WEJ</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID70198443">DTXSID70198443</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q411352#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C3O2/c4-2-1-3-5<sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key:&#160;GNEVIACKFGQMHB-UHFFFAOYSA-N<sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C3O2/c4-2-1-3-5</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key:&#160;GNEVIACKFGQMHB-UHFFFAOYAU</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C=C=C=O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>3</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001680310000000000♠"></span>68.031</span>&#160;g·mol<sup>−1</sup> &#x20; </td></tr> <tr> <td>Appearance </td> <td>colorless gas </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>strong, pungent odor </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>3.0 kg/m<sup>3</sup>, gas<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> <p>1.114 g/cm<sup>3</sup>, liquid<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> </p> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−111.3&#160;°C (−168.3&#160;°F; 161.8&#160;K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>6.8&#160;°C (44.2&#160;°F; 279.9&#160;K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>reacts </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>soluble in <a href="/wiki/1,4-dioxane" class="mw-redirect" title="1,4-dioxane">1,4-dioxane</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>, <a href="/wiki/Xylene" title="Xylene">xylene</a>, <a href="/wiki/Carbon_disulfide" title="Carbon disulfide">CS<sub>2</sub></a>, <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.4538 (6&#160;°C) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>0 D </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Crystal_structure" title="Crystal structure">Crystal structure</a></div> </td> <td>rhombic </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular shape</a></div> </td> <td>quasilinear (phase dependent) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>66.99 J/mol K </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>276.1 J/mol K </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−93.6 kJ/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related oxides</div> </td> <td><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a><br /><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a><br /><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">dicarbon monoxide</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Carbon_subsulfide" title="Carbon subsulfide">carbon subsulfide</a><br /><a href="/wiki/Carbon_subnitride" class="mw-redirect" title="Carbon subnitride">carbon subnitride</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25&#160;°C [77&#160;°F], 100&#160;kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span>&#160;<span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&amp;rev1=445986520&amp;page2=Carbon+suboxide">verify</a></span>&#160;(<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a>&#160;<sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup>&#160;?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Carbon suboxide</b>, or <b>tricarbon dioxide</b>, is an <a href="/wiki/Organic_compound" title="Organic compound">organic</a>, <a href="/wiki/Oxygen" title="Oxygen">oxygen</a>-containing chemical compound with <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <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<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">2</sub></span> and <a href="/wiki/Structural_formula" title="Structural formula">structure</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O=C=C=C=O</span>. Its four cumulative <a href="/wiki/Double_bond" title="Double bond">double bonds</a> make it a <a href="/wiki/Cumulene" title="Cumulene">cumulene</a>. It is one of the stable members of the series of linear <a href="/wiki/Oxocarbon" title="Oxocarbon">oxocarbons</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O=C<sub class="template-chem2-sub"><i>n</i></sub>=O</span>, which also includes <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CO<sub class="template-chem2-sub">2</sub></span>) and <a href="/wiki/Pentacarbon_dioxide" title="Pentacarbon dioxide">pentacarbon dioxide</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">2</sub></span>). Although if carefully purified it can exist at room temperature in the dark without decomposing, it will <a href="/wiki/Polymerize" class="mw-redirect" title="Polymerize">polymerize</a> under certain conditions. </p><p>The substance was discovered in 1873 by <a href="/wiki/Sir_Benjamin_Collins_Brodie,_2nd_Baronet" title="Sir Benjamin Collins Brodie, 2nd Baronet">Benjamin Brodie</a> by subjecting <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> to an electric current. He claimed that the product was part of a series of "oxycarbons" with formulas <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub"><i>x</i>+1</sub>O<sub class="template-chem2-sub"><i>x</i></sub></span>, namely <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>O</span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">2</sub></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">3</sub></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">4</sub></span>, …, and to have identified the last two;<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> however, only <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">2</sub></span> is known. In 1891 <a href="/wiki/Marcellin_Berthelot" title="Marcellin Berthelot">Marcellin Berthelot</a> observed that heating pure carbon monoxide at about 550&#160;°C created small amounts of carbon dioxide but no trace of carbon, and assumed that a carbon-rich oxide was created instead, which he named "sub-oxide". He assumed it was the same product obtained by electric discharge and proposed the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>O</span>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Otto_Diels" title="Otto Diels">Otto Diels</a> later stated that the more organic names dicarbonylmethane and dioxallene were also correct. </p><p>It is commonly described as an oily liquid or gas at room temperature with an extremely noxious odor.<sup id="cite_ref-:0_6-0" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbon_suboxide&amp;action=edit&amp;section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It is synthesized by warming a dry mixture of <a href="/wiki/Phosphorus_pentoxide" title="Phosphorus pentoxide">phosphorus pentoxide</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">P<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">10</sub></span>) and <a href="/wiki/Malonic_acid" title="Malonic acid">malonic acid</a> or its <a href="/wiki/Ester" title="Ester">esters</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> Therefore, it can be also considered as the anhydride of <a href="/wiki/Malonic_anhydride" title="Malonic anhydride">malonic anhydride</a>, i.e. the "second anhydride" of malonic acid.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> </p><p>Several other ways for synthesis and reactions of carbon suboxide can be found in a review from 1930 by Reyerson.<sup id="cite_ref-:0_6-1" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Polymerization">Polymerization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbon_suboxide&amp;action=edit&amp;section=2" title="Edit section: Polymerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbon suboxide polymerizes spontaneously to a red, yellow, or black solid. The structure is postulated to be poly(α-pyronic), similar to the structure in <a href="/wiki/2-pyrone" class="mw-redirect" title="2-pyrone">2-pyrone</a> (α-pyrone).<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Ellern_10-0" class="reference"><a href="#cite_note-Ellern-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup> The number of monomers in the polymers is variable (see <a href="/wiki/Oxocarbon#Polymeric_carbon_oxides" title="Oxocarbon">Oxocarbon#Polymeric carbon oxides</a>). In 1969, it was hypothesized that the color of the Martian surface was caused by this compound; this was disproved by the <a href="/wiki/Viking_program" title="Viking program">Viking Mars probes</a> (the red color is instead due to <a href="/wiki/Iron_oxide" title="Iron oxide">iron oxide</a>).<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbon_suboxide&amp;action=edit&amp;section=3" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbon suboxide is used in the preparation of <a href="/wiki/Malonate" class="mw-redirect" title="Malonate">malonates</a>; and as an auxiliary to improve the dye affinity of furs. </p><p>In <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">chemical synthesis</a>, carbon suboxide is a <a href="/wiki/1,3-dipole" title="1,3-dipole">1,3-dipole</a>, reacting with alkenes to make 1,3&#x2011;cyclopentadiones. Because it is so unstable, it is a reagent of last resort.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biological_role">Biological role</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbon_suboxide&amp;action=edit&amp;section=4" title="Edit section: Biological role"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Carbon_suboxide_macrocyclic_polymers.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Carbon_suboxide_macrocyclic_polymers.gif/220px-Carbon_suboxide_macrocyclic_polymers.gif" decoding="async" width="220" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Carbon_suboxide_macrocyclic_polymers.gif/330px-Carbon_suboxide_macrocyclic_polymers.gif 1.5x, //upload.wikimedia.org/wikipedia/commons/d/d9/Carbon_suboxide_macrocyclic_polymers.gif 2x" data-file-width="364" data-file-height="166" /></a><figcaption>Those are 6- or 8-ring macrocyclic polymers of carbon suboxide that were found in living organisms. They are acting as an endogenous digoxin-like Na+/K+-ATP-ase and Ca-dependent ATP-ase inhibitors, endogenous natriuretics, antioxidants and antihypertensives</figcaption></figure> <p>Carbon suboxide, C<sub>3</sub>O<sub>2</sub>, can be produced in small amounts in any biochemical process that normally produces <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a>, CO, for example, during heme oxidation by heme oxygenase-1. It can also be formed from malonic acid. It has been shown that carbon suboxide in an organism can quickly polymerize into macrocyclic polycarbon structures with the common formula (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">2</sub></span>)<sub>n</sub> (mostly <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">6</sub></span> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">8</sub></span>), and that those macrocyclic compounds are potent inhibitors of Na<sup>+</sup>/K<sup>+</sup>-ATP-ase and Ca-dependent ATP-ase, and have <a href="/wiki/Digoxin" title="Digoxin">digoxin</a>-like physiological properties and natriuretic and antihypertensive actions. Those macrocyclic carbon suboxide polymer compounds are thought to be endogenous digoxin-like regulators of Na<sup>+</sup>/K<sup>+</sup>-ATP-ases and Ca-dependent ATP-ases, and endogenous natriuretics and antihypertensives.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> Other than that, some authors think also that those macrocyclic compounds of carbon suboxide can possibly diminish free radical formation and oxidative stress and play a role in endogenous anticancer protective mechanisms, for example in the <a href="/wiki/Retina" title="Retina">retina</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbon_suboxide&amp;action=edit&amp;section=5" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The structure of carbon suboxide has been the subject of experiments and computations since the 1970s. The central issue is the question of whether the molecule is linear or bent (i.e., whether <span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {\theta _{C2}=\angle C1C2C3\ {\overset {?}{=}}\ 180\!^{\circ }}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mi>&#x03B8;<!-- θ --></mi> <mmultiscripts> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <none /> <none /> <mprescripts /> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mspace width="0pt" height="0pt" depth=".2em" /> </mmultiscripts> <mi mathvariant="normal">&#x2220;<!-- ∠ --></mi> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>&#xA0;</mtext> <mrow class="MJX-TeXAtom-ORD"> <mover> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mo>?</mo> </mover> </mrow> <mtext>&#xA0;</mtext> <mn>180</mn> <mspace width="thinmathspace" /> <msup> <mspace width="negativethinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mo>&#x2218;<!-- ∘ --></mo> </mrow> </msup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {\theta _{C2}=\angle C1C2C3\ {\overset {?}{=}}\ 180\!^{\circ }}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/d65584a203298a50918e00c074fd25ea6c64a4cb" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.671ex; width:22.477ex; height:4.676ex;" alt="{\displaystyle {\ce {\theta _{C2}=\angle C1C2C3\ {\overset {?}{=}}\ 180\!^{\circ }}}}"></span>). Studies generally agree that the molecule is highly non-rigid, with a very shallow barrier to bending. According to one study, the molecular geometry is described by a double-well potential with a minimum at <i>θ</i><sub>C<sub>2</sub></sub> ~ 160°, an inversion barrier of 20&#160;cm<sup>−1</sup> (0.057 kcal/mol), and a total energy change of 80&#160;cm<sup>−1</sup> (0.23 kcal/mol) for 140° ≤ <i>θ</i><sub>C<sub>2</sub></sub> ≤ 180°.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> The small energetic barrier to bending is around the same order of magnitude as the vibrational <a href="/wiki/Zero-point_energy" title="Zero-point energy">zero-point energy</a>. Therefore, the molecule is best described as <i>quasilinear.</i> While infrared<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup> and electron diffraction<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup> studies have indicated that <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">2</sub></span> has a bent structure in the gas phase, the compound was found to possess at least an average linear geometry in the solid phase by X-ray crystallography, although the large thermal ellipsoids of the oxygen atoms and C<sub>2</sub> have been interpreted to be consistent with rapid bending (minimum <i>θ</i><sub>C<sub>2</sub></sub> ~ 170°), even in the solid state.<sup id="cite_ref-Ellern_10-1" class="reference"><a href="#cite_note-Ellern-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup> </p><p>A heterocumulene resonance form of carbon suboxide based on minimization of formal charges does not readily explain the molecule's non-rigidity and deviation from linearity. To account for the quasilinear structure of carbon suboxide, Frenking has proposed that carbon suboxide be regarded as a "coordination complex" of carbon(0) bearing two carbonyl ligands and two lone pairs: <span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\textstyle {\ce {OC:-&gt;{\overset {..}{{\underset {..}{C}}}}&lt;-:CO}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="false" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>OC</mtext> <mo>:&#x27F6;<!-- ⟶ --></mo> <mrow class="MJX-TeXAtom-ORD"> <mover> <mrow class="MJX-TeXAtom-ORD"> <munder> <mtext>C</mtext> <mrow> <mo>&#x22C5;<!-- ⋅ --></mo> <mo>&#x22C5;<!-- ⋅ --></mo> </mrow> </munder> </mrow> <mrow> <mo>&#x22C5;<!-- ⋅ --></mo> <mo>&#x22C5;<!-- ⋅ --></mo> </mrow> </mover> </mrow> <mo stretchy="false">&#x27F5;<!-- ⟵ -->:</mo> <mtext>CO</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\textstyle {\ce {OC:-&gt;{\overset {..}{{\underset {..}{C}}}}&lt;-:CO}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/a89651a5c16d66b977f046fe9f242c0cc612559e" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.367ex; margin-bottom: -0.305ex; width:20.069ex; height:4.509ex;" alt="{\textstyle {\ce {OC:-&gt;{\overset {..}{{\underset {..}{C}}}}&lt;-:CO}}}"></span>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup> However, the contribution of dative bonding in <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">2</sub></span> and similar species has been criticized as chemically unreasonable by others.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Carbon_suboxide_dative.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Carbon_suboxide_dative.png/567px-Carbon_suboxide_dative.png" decoding="async" width="567" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Carbon_suboxide_dative.png/851px-Carbon_suboxide_dative.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Carbon_suboxide_dative.png/1134px-Carbon_suboxide_dative.png 2x" data-file-width="3118" data-file-height="275" /></a><figcaption></figcaption></figure> <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_suboxide&amp;action=edit&amp;section=6" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.webelements.com/compounds/carbon/carbon_suboxide.html">"Carbon Suboxide"</a>. <i>WebElements Periodic Table</i><span class="reference-accessdate">. Retrieved <span class="nowrap">19 Feb</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=WebElements+Periodic+Table&amp;rft.atitle=Carbon+Suboxide&amp;rft_id=https%3A%2F%2Fwww.webelements.com%2Fcompounds%2Fcarbon%2Fcarbon_suboxide.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbon+suboxide" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWeastAstle1983" class="citation book cs1">Weast RC, Astle MJ, eds. (1983). <i>CRC Handbook of Chemistry and Physics</i> (64th&#160;ed.). 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The solution has an intensely acid reaction. The solid deposit, in the dry condition before it has been in contact with the water, is an oxide of carbon.</q></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Proc.+R.+Soc.+Lond.&amp;rft.atitle=Note+on+the+Synthesis+of+Marsh-Gas+and+Formic+Acid%2C+and+on+the+Electric+Decomposition+of+Carbonic+Oxide&amp;rft.volume=21&amp;rft.issue=139%E2%80%93147&amp;rft.pages=245-247&amp;rft.date=1873&amp;rft_id=info%3Adoi%2F10.1098%2Frspl.1872.0052&amp;rft_id=https%3A%2F%2Fwww.jstor.org%2Fstable%2F113037%23id-name%3DJSTOR&amp;rft.aulast=Brodie&amp;rft.aufirst=BC&amp;rft_id=https%3A%2F%2Fdoi.org%2F10.1098%252Frspl.1872.0052&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbon+suboxide" 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="CITEREFBrodie1873" class="citation journal cs1">Brodie BC (1873). <a rel="nofollow" class="external text" href="https://archive.org/stream/justusliebigsan01unkngoog#page/n282/mode/2up">"Ueber eine Synthese von Sumpfgas und Ameisensäure und die electrische Zersetzung des Kohlenoxyds"</a>. <i><a href="/wiki/Annalen_der_Chemie" class="mw-redirect" title="Annalen der Chemie">Liebigs Ann.</a></i> <b>169</b> (1–2): 270–271. <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%2Fjlac.18731690119">10.1002/jlac.18731690119</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Liebigs+Ann.&amp;rft.atitle=Ueber+eine+Synthese+von+Sumpfgas+und+Ameisens%C3%A4ure+und+die+electrische+Zersetzung+des+Kohlenoxyds&amp;rft.volume=169&amp;rft.issue=1%E2%80%932&amp;rft.pages=270-271&amp;rft.date=1873&amp;rft_id=info%3Adoi%2F10.1002%2Fjlac.18731690119&amp;rft.aulast=Brodie&amp;rft.aufirst=BC&amp;rft_id=https%3A%2F%2Farchive.org%2Fstream%2Fjustusliebigsan01unkngoog%23page%2Fn282%2Fmode%2F2up&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbon+suboxide" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBerthelot1891" class="citation journal cs1"><a href="/wiki/Marcellin_Berthelot" title="Marcellin Berthelot">Berthelot M</a> (1891). <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k34894x/f124.table">"Action de la chaleur sur l'oxyde de carbone"</a>. <i><a href="/wiki/Annales_de_Chimie_et_de_Physique" class="mw-redirect" title="Annales de Chimie et de Physique">Annales de Chimie et de Physique</a></i>. <b>6</b> (24): 126–132. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20120217183140/http://gallica.bnf.fr/ark:/12148/bpt6k34894x/f124.table">Archived</a> from the original on 17 February 2012<span class="reference-accessdate">. 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Lett.</a></i> <b>6</b> (5): 452–456. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1970CPL.....6..452C">1970CPL.....6..452C</a>. <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%2F0009-2614%2870%2985190-9">10.1016/0009-2614(70)85190-9</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Chem.+Phys.+Lett.&amp;rft.atitle=The+potential+function+for+the+CCC+bending+in+carbon+suboxide&amp;rft.volume=6&amp;rft.issue=5&amp;rft.pages=452-456&amp;rft.date=1970&amp;rft_id=info%3Adoi%2F10.1016%2F0009-2614%2870%2985190-9&amp;rft_id=info%3Abibcode%2F1970CPL.....6..452C&amp;rft.aulast=Clark&amp;rft.aufirst=A&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbon+suboxide" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFrenkingTonner2009" class="citation journal cs1">Frenking G, Tonner R (2009). <a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fpac-con-08-11-03">"Divalent carbon(0) compounds"</a>. <i><a href="/wiki/Pure_and_Applied_Chemistry" title="Pure and Applied Chemistry">Pure Appl. Chem.</a></i> <b>81</b> (4): 597–614. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fpac-con-08-11-03">10.1351/pac-con-08-11-03</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a>&#160;<a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1365-3075">1365-3075</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:98257123">98257123</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Pure+Appl.+Chem.&amp;rft.atitle=Divalent+carbon%280%29+compounds&amp;rft.volume=81&amp;rft.issue=4&amp;rft.pages=597-614&amp;rft.date=2009&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A98257123%23id-name%3DS2CID&amp;rft.issn=1365-3075&amp;rft_id=info%3Adoi%2F10.1351%2Fpac-con-08-11-03&amp;rft.aulast=Frenking&amp;rft.aufirst=G&amp;rft.au=Tonner%2C+R&amp;rft_id=https%3A%2F%2Fdoi.org%2F10.1351%252Fpac-con-08-11-03&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbon+suboxide" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHimmelKrossingSchnepf2014" class="citation journal cs1">Himmel D, Krossing I, Schnepf A (2014). "Dative Bonds in Main-Group Compounds: A Case for Fewer Arrows!". <i>Angewandte Chemie International Edition</i>. <b>53</b> (2): 370–374. <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.201300461">10.1002/anie.201300461</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a>&#160;<a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1521-3773">1521-3773</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24243854">24243854</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Angewandte+Chemie+International+Edition&amp;rft.atitle=Dative+Bonds+in+Main-Group+Compounds%3A+A+Case+for+Fewer+Arrows%21&amp;rft.volume=53&amp;rft.issue=2&amp;rft.pages=370-374&amp;rft.date=2014&amp;rft.issn=1521-3773&amp;rft_id=info%3Apmid%2F24243854&amp;rft_id=info%3Adoi%2F10.1002%2Fanie.201300461&amp;rft.aulast=Himmel&amp;rft.aufirst=D&amp;rft.au=Krossing%2C+I&amp;rft.au=Schnepf%2C+A&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbon+suboxide" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbon_suboxide&amp;action=edit&amp;section=7" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" 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class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Carbon_pentoxide" title="Carbon pentoxide"><span class="chemf nowrap">CO<sub class="template-chem2-sub">5</sub></span></a></li> <li><a href="/wiki/Carbon_hexoxide" title="Carbon hexoxide"><span class="chemf nowrap">CO<sub class="template-chem2-sub">6</sub></span></a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>O</span></a></li> <li><a href="/wiki/Ethylene_dione" title="Ethylene dione"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Oxalic_anhydride" title="Oxalic anhydride"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">3</sub></span></a></li> <li><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">4</sub></span> (<a href="/wiki/1,2-Dioxetanedione" title="1,2-Dioxetanedione">1,2-Dioxetanedione</a> and <a href="/wiki/1,3-Dioxetanedione" title="1,3-Dioxetanedione">1,3-Dioxetanedione</a>)</li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>O</span></a></li> <li><a class="mw-selflink selflink"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Cyclopropanetrione" title="Cyclopropanetrione"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">3</sub></span></a></li> <li><a href="/wiki/1,3,5-Trioxanetrione" title="1,3,5-Trioxanetrione"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>O<sub class="template-chem2-sub">6</sub></span></a></li> <li><a href="/wiki/Tetracarbon_dioxide" title="Tetracarbon dioxide"><span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Cyclobutanetetrone" title="Cyclobutanetetrone"><span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Dioxane_tetraketone" title="Dioxane tetraketone"><span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">6</sub></span></a></li> <li><a href="/wiki/Pentacarbon_dioxide" title="Pentacarbon dioxide"><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Cyclopentanepentone" title="Cyclopentanepentone"><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">5</sub></span></a></li> <li><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>O<sub class="template-chem2-sub">6</sub></span> (<a href="/wiki/Cyclohexanehexone" title="Cyclohexanehexone">Cyclohexanehexone</a> and <a href="/wiki/Ethylenetetracarboxylic_dianhydride" title="Ethylenetetracarboxylic dianhydride">Ethylenetetracarboxylic dianhydride</a>)</li> <li><a href="/wiki/Tetrahydroxy-1,4-benzoquinone_biscarbonate" title="Tetrahydroxy-1,4-benzoquinone biscarbonate"><span class="chemf nowrap">C<sub class="template-chem2-sub">8</sub>O<sub class="template-chem2-sub">8</sub></span></a></li> <li><a href="/wiki/Hexahydroxybenzene_triscarbonate" title="Hexahydroxybenzene triscarbonate"><span class="chemf nowrap">C<sub class="template-chem2-sub">9</sub>O<sub class="template-chem2-sub">9</sub></span></a></li> <li><a href="/wiki/Benzoquinonetetracarboxylic_dianhydride" title="Benzoquinonetetracarboxylic dianhydride"><span class="chemf nowrap">C<sub class="template-chem2-sub">10</sub>O<sub class="template-chem2-sub">8</sub></span></a></li> <li><a href="/wiki/Tetrahydroxy-1,4-benzoquinone_bisoxalate" title="Tetrahydroxy-1,4-benzoquinone bisoxalate"><span class="chemf nowrap">C<sub class="template-chem2-sub">10</sub>O<sub class="template-chem2-sub">10</sub></span></a></li> <li><a href="/wiki/Hexaoxotricyclobutabenzene" title="Hexaoxotricyclobutabenzene"><span class="chemf nowrap">C<sub class="template-chem2-sub">12</sub>O<sub class="template-chem2-sub">6</sub></span></a></li> <li><a href="/wiki/Mellitic_anhydride" title="Mellitic anhydride"><span class="chemf nowrap">C<sub class="template-chem2-sub">12</sub>O<sub class="template-chem2-sub">9</sub></span></a></li> <li><a href="/wiki/Hexahydroxybenzene_trisoxalate" title="Hexahydroxybenzene trisoxalate"><span class="chemf nowrap">C<sub class="template-chem2-sub">12</sub>O<sub class="template-chem2-sub">12</sub></span></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Polymers</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Graphite_oxide" title="Graphite oxide">Graphite oxide</a></li> <li><a href="/w/index.php?title=Polymeric_carbon_suboxide&amp;action=edit&amp;redlink=1" class="new" title="Polymeric carbon suboxide (page does not exist)">C<sub>3</sub>O<sub>2</sub></a></li> <li><a href="/wiki/Polycarbonyl" title="Polycarbonyl">CO</a></li> <li><a href="/w/index.php?title=Polymeric_carbon_dioxide&amp;action=edit&amp;redlink=1" class="new" title="Polymeric carbon dioxide (page does not exist)">CO<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Compounds derived from oxides</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Metal_carbonyl" title="Metal carbonyl">Metal carbonyls</a></li> <li><a href="/wiki/Carbonic_acid" title="Carbonic acid">Carbonic acid</a></li> <li><a href="/wiki/Bicarbonate" title="Bicarbonate">Bicarbonates</a></li> <li><a href="/wiki/Carbonate" title="Carbonate">Carbonates</a></li> <li><a href="/wiki/Polycarbonate_(functional_group)" title="Polycarbonate (functional group)">Polycarbonates</a> (<a href="/wiki/Dicarbonate" title="Dicarbonate">Dicarbonates</a> and <a href="/wiki/Tricarbonate" title="Tricarbonate">Tricarbonates</a>)</li> <li><a href="/wiki/Peroxydicarbonate" title="Peroxydicarbonate">Peroxydicarbonates</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"></div><div role="navigation" class="navbox" aria-labelledby="Inorganic_compounds_of_carbon_and_related_ions" 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:Inorganic_compounds_of_carbon" title="Template:Inorganic compounds of carbon"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Inorganic_compounds_of_carbon" title="Template talk:Inorganic compounds of carbon"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Inorganic_compounds_of_carbon" title="Special:EditPage/Template:Inorganic compounds of carbon"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Inorganic_compounds_of_carbon_and_related_ions" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_inorganic_compounds" title="List of inorganic compounds">Inorganic compounds of</a> <a href="/wiki/Carbon" title="Carbon">carbon</a> and related ions</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Compounds</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carbon_monofluoride" title="Carbon monofluoride">CF</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">CO</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></li> <li><a href="/wiki/Carbon_trioxide" title="Carbon trioxide">CO<sub>3</sub></a></li> <li><a href="/wiki/Carbon_tetroxide" title="Carbon tetroxide">CO<sub>4</sub></a></li> <li><a href="/wiki/Carbon_pentoxide" title="Carbon pentoxide">CO<sub>5</sub></a></li> <li><a href="/wiki/Carbon_hexoxide" title="Carbon hexoxide">CO<sub>6</sub></a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">COS</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">CS</a></li> <li><a href="/wiki/Ethenedithione" title="Ethenedithione">C<sub>2</sub>S<sub>2</sub></a></li> <li><a href="/wiki/Carbon_disulfide" title="Carbon disulfide">CS<sub>2</sub></a></li> <li><a href="/wiki/Carbon_diselenide" title="Carbon diselenide">CSe<sub>2</sub></a></li> <li><a class="mw-selflink selflink">C<sub>3</sub>O<sub>2</sub></a></li> <li><a href="/wiki/Carbon_subsulfide" title="Carbon subsulfide">C<sub>3</sub>S<sub>2</sub></a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">SiC</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Carbon ions</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carbide" title="Carbide">Carbides</a> [:C≡C:]<sup>2−</sup>, [::C::]<sup>4−</sup>, [:C=C=C:]<sup>4−</sup></li> <li><a href="/wiki/Cyanide" title="Cyanide">Cyanide</a> [:C≡N:]<sup>−</sup></li> <li><a href="/wiki/Cyanate" title="Cyanate">Cyanate</a> [:O−C≡N:]<sup>−</sup></li> <li><a href="/wiki/Thiocyanate" title="Thiocyanate">Thiocyanate</a> [:S−C≡N:]<sup>−</sup></li> <li><a href="/wiki/Fulminate" title="Fulminate">Fulminate</a> [:C≡N−O:]<sup>−</sup></li> <li><a href="https://www.wikidata.org/wiki/Q27110079" class="extiw" title="wikidata:Q27110079">Thiofulminate</a> [:C≡N−S:]<sup>−</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nanostructures</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Graphite_intercalation_compounds" class="mw-redirect" title="Graphite intercalation compounds">Graphite intercalation compounds</a></li> <li><a href="/wiki/Fulleride" title="Fulleride">Fullerides</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Oxides and related</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oxocarbon" title="Oxocarbon">Oxides</a></li> <li><a href="/wiki/Carbon_nitride" title="Carbon nitride">Nitrides</a></li> <li><a href="/wiki/Metal_carbonyl" title="Metal carbonyl">Metal carbonyls</a></li> <li><a href="/wiki/Carbonic_acid" title="Carbonic acid">Carbonic acid</a></li> <li><a href="/wiki/Bicarbonate" title="Bicarbonate">Bicarbonates</a></li> <li><a href="/wiki/Carbonate" title="Carbonate">Carbonates</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"></div><div role="navigation" class="navbox" aria-labelledby="Oxides" 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:Oxides" title="Template:Oxides"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Oxides" title="Template talk:Oxides"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Oxides" title="Special:EditPage/Template:Oxides"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Oxides" style="font-size:114%;margin:0 4em"><a href="/wiki/Oxide" title="Oxide">Oxides</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Mixed oxidation states</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antimony_tetroxide" title="Antimony tetroxide">Antimony tetroxide</a> (<a href="/wiki/Antimony" title="Antimony">Sb</a><sub>2</sub>O<sub>4</sub>)</li> <li><a href="/wiki/Boron_suboxide" title="Boron suboxide">Boron suboxide</a> (<a href="/wiki/Boron" title="Boron">B</a><sub>12</sub>O<sub>2</sub>)</li> <li><a class="mw-selflink selflink">Carbon suboxide</a> (<a href="/wiki/Carbon" title="Carbon">C</a><sub>3</sub>O<sub>2</sub>)</li> <li><a href="/wiki/Chlorine_perchlorate" title="Chlorine perchlorate">Chlorine perchlorate</a> (<a href="/wiki/Chlorine" title="Chlorine">Cl</a><sub>2</sub>O<sub>4</sub>)</li> <li><a href="/wiki/Chloryl_perchlorate" class="mw-redirect" title="Chloryl perchlorate">Chloryl perchlorate</a> (<a href="/wiki/Chlorine" title="Chlorine">Cl</a><sub>2</sub>O<sub>6</sub>)</li> <li><a href="/wiki/Cobalt(II,III)_oxide" title="Cobalt(II,III) oxide">Cobalt(II,III) oxide</a> (<a href="/wiki/Cobalt" title="Cobalt">Co</a><sub>3</sub>O<sub>4</sub>)</li> <li><a href="/wiki/Dichlorine_pentoxide" title="Dichlorine pentoxide">Dichlorine pentoxide</a> (<a href="/wiki/Chlorine" title="Chlorine">Cl</a><sub>2</sub>O<sub>5</sub>)</li> <li><a href="/wiki/Iron(II,III)_oxide" title="Iron(II,III) oxide">Iron(II,III) oxide</a> (<a href="/wiki/Iron" title="Iron">Fe</a><sub>3</sub>O<sub>4</sub>)</li> <li><a href="/wiki/Lead(II,IV)_oxide" title="Lead(II,IV) oxide">Lead(II,IV) oxide</a> (<a href="/wiki/Lead" title="Lead">Pb</a><sub>3</sub>O<sub>4</sub>)</li> <li><a href="/wiki/Manganese(II,III)_oxide" title="Manganese(II,III) oxide">Manganese(II,III) oxide</a> (<a href="/wiki/Manganese" title="Manganese">Mn</a><sub>3</sub>O<sub>4</sub>)</li> <li><a href="/wiki/Mellitic_anhydride" title="Mellitic anhydride">Mellitic anhydride</a> (<a href="/wiki/Carbon" title="Carbon">C</a><sub>12</sub>O<sub>9</sub>)</li> <li><a href="/wiki/Praseodymium(III,IV)_oxide" title="Praseodymium(III,IV) oxide">Praseodymium(III,IV) oxide</a> (<a href="/wiki/Praseodymium" title="Praseodymium">Pr</a><sub>6</sub>O<sub>11</sub>)</li> <li><a href="/wiki/Silver(I,III)_oxide" title="Silver(I,III) oxide">Silver(I,III) oxide</a> (<a href="/wiki/Silver" title="Silver">Ag</a><sub>2</sub>O<sub>2</sub>)</li> <li><a href="/wiki/Terbium(III,IV)_oxide" title="Terbium(III,IV) oxide">Terbium(III,IV) oxide</a> (<a href="/wiki/Terbium" title="Terbium">Tb</a><sub>4</sub>O<sub>7</sub>)</li> <li><a href="/wiki/Tribromine_octoxide" title="Tribromine octoxide">Tribromine octoxide</a> (<a href="/wiki/Bromine" title="Bromine">Br</a><sub>3</sub>O<sub>8</sub>)</li> <li><a href="/wiki/Triuranium_octoxide" title="Triuranium octoxide">Triuranium octoxide</a> (<a href="/wiki/Uranium" title="Uranium">U</a><sub>3</sub>O<sub>8</sub>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">+1 oxidation state</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium(I)_oxide" title="Aluminium(I) oxide">Aluminium(I) oxide</a> (<a href="/wiki/Aluminium" title="Aluminium">Al</a><sub>2</sub>O)</li> <li><a href="/wiki/Copper(I)_oxide" title="Copper(I) oxide">Copper(I) oxide</a> (<a href="/wiki/Copper" title="Copper">Cu</a><sub>2</sub>O)</li> <li><a href="/wiki/Caesium_monoxide" title="Caesium monoxide">Caesium monoxide</a> (<a href="/wiki/Caesium" title="Caesium">Cs</a><sub>2</sub>O)</li> <li><a href="/wiki/Dibromine_monoxide" title="Dibromine monoxide">Dibromine monoxide</a> (<a href="/wiki/Bromine" title="Bromine">Br</a><sub>2</sub>O)</li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a> (<a href="/wiki/Carbon" title="Carbon">C</a><sub>2</sub>O)</li> <li><a href="/wiki/Dichlorine_monoxide" title="Dichlorine monoxide">Dichlorine monoxide</a> (<a href="/wiki/Chlorine" title="Chlorine">Cl</a><sub>2</sub>O)</li> <li><a href="/wiki/Gallium(I)_oxide" title="Gallium(I) oxide">Gallium(I) oxide</a> (<a href="/wiki/Gallium" title="Gallium">Ga</a><sub>2</sub>O)</li> <li><a href="/wiki/Iodine(I)_oxide" class="mw-redirect" title="Iodine(I) oxide">Iodine(I) oxide</a> (<a href="/wiki/Iodine" title="Iodine">I</a><sub>2</sub>O)</li> <li><a href="/wiki/Lithium_oxide" title="Lithium oxide">Lithium oxide</a> (<a href="/wiki/Lithium" title="Lithium">Li</a><sub>2</sub>O)</li> <li><a href="/wiki/Mercury(I)_oxide" title="Mercury(I) oxide">Mercury(I) oxide</a> (<a href="/wiki/Mercury_(element)" title="Mercury (element)">Hg</a><sub>2</sub>O)</li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a> (<a href="/wiki/Nitrogen" title="Nitrogen">N</a><sub>2</sub>O)</li> <li><a href="/wiki/Potassium_oxide" title="Potassium oxide">Potassium oxide</a> (<a href="/wiki/Potassium" title="Potassium">K</a><sub>2</sub>O)</li> <li><a href="/wiki/Rubidium_oxide" title="Rubidium oxide">Rubidium oxide</a> (<a href="/wiki/Rubidium" title="Rubidium">Rb</a><sub>2</sub>O)</li> <li><a href="/wiki/Silver_oxide" title="Silver oxide">Silver oxide</a> (<a href="/wiki/Silver" title="Silver">Ag</a><sub>2</sub>O)</li> <li><a href="/wiki/Thallium(I)_oxide" title="Thallium(I) oxide">Thallium(I) oxide</a> (<a href="/wiki/Thallium" title="Thallium">Tl</a><sub>2</sub>O)</li> <li><a href="/wiki/Sodium_oxide" title="Sodium oxide">Sodium oxide</a> (<a href="/wiki/Sodium" title="Sodium">Na</a><sub>2</sub>O)</li> <li><a href="/wiki/Properties_of_water" title="Properties of water">Water (hydrogen oxide)</a> (<a href="/wiki/Hydrogen" title="Hydrogen">H</a><sub>2</sub>O)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">+2 oxidation state</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium(II)_oxide" title="Aluminium(II) oxide">Aluminium(II) oxide</a> (<a href="/wiki/Aluminium" title="Aluminium">Al</a>O)</li> <li><a href="/wiki/Barium_oxide" title="Barium oxide">Barium oxide</a> (<a href="/wiki/Barium" title="Barium">Ba</a>O)</li> <li><a href="/wiki/Berkelium_monoxide" class="mw-redirect" title="Berkelium monoxide">Berkelium monoxide</a> (<a href="/wiki/Berkelium" title="Berkelium">Bk</a>O)</li> <li><a href="/wiki/Beryllium_oxide" title="Beryllium oxide">Beryllium oxide</a> (<a href="/wiki/Beryllium" title="Beryllium">Be</a>O)</li> <li><a href="/wiki/Boron_monoxide" title="Boron monoxide">Boron monoxide</a> (<a href="/wiki/Boron" title="Boron">B</a>O)</li> <li><a href="/wiki/Bromine_monoxide" class="mw-redirect" title="Bromine monoxide">Bromine monoxide</a> (<a href="/wiki/Bromine" title="Bromine">Br</a>O)</li> <li><a href="/wiki/Cadmium_oxide" title="Cadmium oxide">Cadmium oxide</a> (<a href="/wiki/Cadmium" title="Cadmium">Cd</a>O)</li> <li><a href="/wiki/Calcium_oxide" title="Calcium oxide">Calcium oxide</a> (<a href="/wiki/Calcium" title="Calcium">Ca</a>O)</li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a> (<a href="/wiki/Carbon" title="Carbon">C</a>O)</li> <li><a href="/wiki/Chlorine_monoxide" title="Chlorine monoxide">Chlorine monoxide</a> (<a href="/wiki/Chlorine" title="Chlorine">Cl</a>O)</li> <li><a href="/wiki/Chromium(II)_oxide" title="Chromium(II) oxide">Chromium(II) oxide</a> (<a href="/wiki/Chromium" title="Chromium">Cr</a>O)</li> <li><a href="/wiki/Cobalt(II)_oxide" title="Cobalt(II) oxide">Cobalt(II) oxide</a> (<a href="/wiki/Cobalt" title="Cobalt">Co</a>O)</li> <li><a href="/wiki/Copper(II)_oxide" title="Copper(II) oxide">Copper(II) oxide</a> (<a href="/wiki/Copper" title="Copper">Cu</a>O)</li> <li><a href="/wiki/Dinitrogen_dioxide" title="Dinitrogen dioxide">Dinitrogen dioxide</a> (<a href="/wiki/Nitrogen" title="Nitrogen">N</a><sub>2</sub>O<sub>2</sub>)</li> <li><a href="/wiki/Europium(II)_oxide" title="Europium(II) oxide">Europium(II) oxide</a> (<a href="/wiki/Europium" title="Europium">Eu</a>O)</li> <li><a href="/wiki/Germanium_monoxide" title="Germanium monoxide">Germanium monoxide</a> (<a href="/wiki/Germanium" title="Germanium">Ge</a>O)</li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">Iron(II) oxide</a> (<a href="/wiki/Iron" title="Iron">Fe</a>O)</li> <li><a href="/wiki/Iodine_monoxide" title="Iodine monoxide">Iodine monoxide</a> (<a href="/wiki/Iodine" title="Iodine">I</a>O)</li> <li><a href="/wiki/Lead(II)_oxide" title="Lead(II) oxide">Lead(II) oxide</a> (<a href="/wiki/Lead" title="Lead">Pb</a>O)</li> <li><a href="/wiki/Magnesium_oxide" title="Magnesium oxide">Magnesium oxide</a> (<a href="/wiki/Magnesium" title="Magnesium">Mg</a>O)</li> <li><a href="/wiki/Manganese(II)_oxide" title="Manganese(II) oxide">Manganese(II) oxide</a> (<a href="/wiki/Manganese" title="Manganese">Mn</a>O)</li> <li><a href="/wiki/Mercury(II)_oxide" title="Mercury(II) oxide">Mercury(II) oxide</a> (<a href="/wiki/Mercury_(element)" title="Mercury (element)">Hg</a>O)</li> <li><a href="/wiki/Nickel(II)_oxide" title="Nickel(II) oxide">Nickel(II) oxide</a> (<a href="/wiki/Nickel" title="Nickel">Ni</a>O)</li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a> (<a href="/wiki/Nitrogen" title="Nitrogen">N</a>O)</li> <li><a href="/wiki/Niobium_monoxide" title="Niobium monoxide">Niobium monoxide</a> (<a href="/wiki/Niobium" title="Niobium">Nb</a>O)</li> <li><a href="/wiki/Palladium(II)_oxide" title="Palladium(II) oxide">Palladium(II) oxide</a> (<a href="/wiki/Palladium" title="Palladium">Pd</a>O)</li> <li><a href="/wiki/Phosphorus_monoxide" title="Phosphorus monoxide">Phosphorus monoxide</a> (<a href="/wiki/Phosphorus" title="Phosphorus">P</a>O)</li> <li><a href="/wiki/Polonium_monoxide" title="Polonium monoxide">Polonium monoxide</a> (<a href="/wiki/Polonium" title="Polonium">Po</a>O)</li> <li><a href="/wiki/Protactinium_monoxide" title="Protactinium monoxide">Protactinium monoxide</a> (<a href="/wiki/Protactinium" title="Protactinium">Pa</a>O)</li> <li><a href="/wiki/Radium_oxide" title="Radium oxide">Radium oxide</a> (<a href="/wiki/Radium" title="Radium">Ra</a>O)</li> <li><a href="/wiki/Silicon_monoxide" title="Silicon monoxide">Silicon monoxide</a> (<a href="/wiki/Silicon" title="Silicon">Si</a>O)</li> <li><a href="/wiki/Strontium_oxide" title="Strontium oxide">Strontium oxide</a> (<a href="/wiki/Strontium" title="Strontium">Sr</a>O)</li> <li><a href="/wiki/Sulfur_monoxide" title="Sulfur monoxide">Sulfur monoxide</a> (<a href="/wiki/Sulfur" title="Sulfur">S</a>O)</li> <li><a href="/wiki/Disulfur_dioxide" title="Disulfur dioxide">Disulfur dioxide</a> (<a href="/wiki/Sulfur" title="Sulfur">S</a><sub>2</sub>O<sub>2</sub>)</li> <li><a href="/wiki/Thorium_monoxide" title="Thorium monoxide">Thorium monoxide</a> (<a href="/wiki/Thorium" title="Thorium">Th</a>O)</li> <li><a href="/wiki/Tin(II)_oxide" title="Tin(II) oxide">Tin(II) oxide</a> (<a href="/wiki/Tin" title="Tin">Sn</a>O)</li> <li><a href="/wiki/Titanium(II)_oxide" title="Titanium(II) oxide">Titanium(II) oxide</a> (<a href="/wiki/Titanium" title="Titanium">Ti</a>O)</li> <li><a href="/wiki/Vanadium(II)_oxide" title="Vanadium(II) oxide">Vanadium(II) oxide</a> (<a href="/wiki/Vanadium" title="Vanadium">V</a>O)</li> <li><a href="/wiki/Yttrium(II)_oxide" title="Yttrium(II) oxide">Yttrium(II) oxide</a> (<a href="/wiki/Yttrium" title="Yttrium">Y</a>O)</li> <li><a href="/wiki/Zirconium_monoxide" class="mw-redirect" title="Zirconium monoxide">Zirconium monoxide</a> (<a href="/wiki/Zirconium" title="Zirconium">Zr</a>O)</li> <li><a href="/wiki/Zinc_oxide" title="Zinc oxide">Zinc oxide</a> (<a href="/wiki/Zinc" title="Zinc">Zn</a>O)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">+3 oxidation state</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Actinium(III)_oxide" title="Actinium(III) oxide">Actinium(III) oxide</a> (<a href="/wiki/Actinium" title="Actinium">Ac</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Aluminium_oxide" title="Aluminium oxide">Aluminium oxide</a> (<a href="/wiki/Aluminium" title="Aluminium">Al</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Americium(III)_oxide" title="Americium(III) oxide">Americium(III) oxide</a> (<a href="/wiki/Americium" title="Americium">Am</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Antimony_trioxide" title="Antimony trioxide">Antimony trioxide</a> (<a href="/wiki/Antimony" title="Antimony">Sb</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Arsenic_trioxide" title="Arsenic trioxide">Arsenic trioxide</a> (<a href="/wiki/Arsenic" title="Arsenic">As</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Berkelium(III)_oxide" title="Berkelium(III) oxide">Berkelium(III) oxide</a> (<a href="/wiki/Berkelium" title="Berkelium">Bk</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Bismuth(III)_oxide" title="Bismuth(III) oxide">Bismuth(III) oxide</a> (<a href="/wiki/Bismuth" title="Bismuth">Bi</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Boron_trioxide" title="Boron trioxide">Boron trioxide</a> (<a href="/wiki/Boron" title="Boron">B</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Caesium_sesquioxide" title="Caesium sesquioxide">Caesium sesquioxide</a> (<a href="/wiki/Caesium" title="Caesium">Cs</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Californium(III)_oxide" title="Californium(III) oxide">Californium(III) oxide</a> (<a href="/wiki/Californium" title="Californium">Cf</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Cerium(III)_oxide" title="Cerium(III) oxide">Cerium(III) oxide</a> (<a href="/wiki/Cerium" title="Cerium">Ce</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Chromium(III)_oxide" title="Chromium(III) oxide">Chromium(III) oxide</a> (<a href="/wiki/Chromium" title="Chromium">Cr</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Cobalt(III)_oxide" title="Cobalt(III) oxide">Cobalt(III) oxide</a> (<a href="/wiki/Cobalt" title="Cobalt">Co</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Dinitrogen_trioxide" title="Dinitrogen trioxide">Dinitrogen trioxide</a> (<a href="/wiki/Nitrogen" title="Nitrogen">N</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Dysprosium(III)_oxide" title="Dysprosium(III) oxide">Dysprosium(III) oxide</a> (<a href="/wiki/Dysprosium" title="Dysprosium">Dy</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Einsteinium(III)_oxide" title="Einsteinium(III) oxide">Einsteinium(III) oxide</a> (<a href="/wiki/Einsteinium" title="Einsteinium">Es</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Erbium(III)_oxide" title="Erbium(III) oxide">Erbium(III) oxide</a> (<a href="/wiki/Erbium" title="Erbium">Er</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Europium(III)_oxide" title="Europium(III) oxide">Europium(III) oxide</a> (<a href="/wiki/Europium" title="Europium">Eu</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Gadolinium(III)_oxide" title="Gadolinium(III) oxide">Gadolinium(III) oxide</a> (<a href="/wiki/Gadolinium" title="Gadolinium">Gd</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Gallium(III)_oxide" title="Gallium(III) oxide">Gallium(III) oxide</a> (<a href="/wiki/Gallium" title="Gallium">Ga</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Gold(III)_oxide" title="Gold(III) oxide">Gold(III) oxide</a> (<a href="/wiki/Gold" title="Gold">Au</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Holmium(III)_oxide" title="Holmium(III) oxide">Holmium(III) oxide</a> (<a href="/wiki/Holmium" title="Holmium">Ho</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Indium(III)_oxide" title="Indium(III) oxide">Indium(III) oxide</a> (<a href="/wiki/Indium" title="Indium">In</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Iron(III)_oxide" title="Iron(III) oxide">Iron(III) oxide</a> (<a href="/wiki/Iron" title="Iron">Fe</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Lanthanum_oxide" title="Lanthanum oxide">Lanthanum oxide</a> (<a href="/wiki/Lanthanum" title="Lanthanum">La</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Lutetium(III)_oxide" title="Lutetium(III) oxide">Lutetium(III) oxide</a> (<a href="/wiki/Lutetium" title="Lutetium">Lu</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Manganese(III)_oxide" title="Manganese(III) oxide">Manganese(III) oxide</a> (<a href="/wiki/Manganese" title="Manganese">Mn</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Neodymium(III)_oxide" title="Neodymium(III) oxide">Neodymium(III) oxide</a> (<a href="/wiki/Neodymium" title="Neodymium">Nd</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Nickel(III)_oxide" title="Nickel(III) oxide">Nickel(III) oxide</a> (<a href="/wiki/Nickel" title="Nickel">Ni</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Phosphorus_trioxide" title="Phosphorus trioxide">Phosphorus trioxide</a> (<a href="/wiki/Phosphorus" title="Phosphorus">P</a><sub>4</sub>O<sub>6</sub>)</li> <li><a href="/wiki/Praseodymium(III)_oxide" title="Praseodymium(III) oxide">Praseodymium(III) oxide</a> (<a href="/wiki/Praseodymium" title="Praseodymium">Pr</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Promethium(III)_oxide" title="Promethium(III) oxide">Promethium(III) oxide</a> (<a href="/wiki/Promethium" title="Promethium">Pm</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Rhodium(III)_oxide" title="Rhodium(III) oxide">Rhodium(III) oxide</a> (<a href="/wiki/Rhodium" title="Rhodium">Rh</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Samarium(III)_oxide" title="Samarium(III) oxide">Samarium(III) oxide</a> (<a href="/wiki/Samarium" title="Samarium">Sm</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Scandium_oxide" title="Scandium oxide">Scandium oxide</a> (<a href="/wiki/Scandium" title="Scandium">Sc</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Terbium(III)_oxide" title="Terbium(III) oxide">Terbium(III) oxide</a> (<a href="/wiki/Terbium" title="Terbium">Tb</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Thallium(III)_oxide" title="Thallium(III) oxide">Thallium(III) oxide</a> (<a href="/wiki/Thallium" title="Thallium">Tl</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Thulium(III)_oxide" title="Thulium(III) oxide">Thulium(III) oxide</a> (<a href="/wiki/Thulium" title="Thulium">Tm</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Titanium(III)_oxide" title="Titanium(III) oxide">Titanium(III) oxide</a> (<a href="/wiki/Titanium" title="Titanium">Ti</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Tungsten(III)_oxide" title="Tungsten(III) oxide">Tungsten(III) oxide</a> (<a href="/wiki/Tungsten" title="Tungsten">W</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Vanadium(III)_oxide" title="Vanadium(III) oxide">Vanadium(III) oxide</a> (<a href="/wiki/Vanadium" title="Vanadium">V</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Ytterbium(III)_oxide" title="Ytterbium(III) oxide">Ytterbium(III) oxide</a> (<a href="/wiki/Ytterbium" title="Ytterbium">Yb</a><sub>2</sub>O<sub>3</sub>)</li> <li><a href="/wiki/Yttrium(III)_oxide" title="Yttrium(III) oxide">Yttrium(III) oxide</a> (<a href="/wiki/Yttrium" title="Yttrium">Y</a><sub>2</sub>O<sub>3</sub>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">+4 oxidation state</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Americium_dioxide" title="Americium dioxide">Americium dioxide</a> (<a href="/wiki/Americium" title="Americium">Am</a>O<sub>2</sub>)</li> <li><a href="/wiki/Berkelium(IV)_oxide" title="Berkelium(IV) oxide">Berkelium(IV) oxide</a> (<a href="/wiki/Berkelium" title="Berkelium">Bk</a>O<sub>2</sub>)</li> <li><a href="/wiki/Bromine_dioxide" title="Bromine dioxide">Bromine dioxide</a> (<a href="/wiki/Bromine" title="Bromine">Br</a>O<sub>2</sub>)</li> <li><a href="/wiki/Californium_dioxide" class="mw-redirect" title="Californium dioxide">Californium dioxide</a> (<a href="/wiki/Californium" title="Californium">Cf</a>O<sub>2</sub>)</li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a> (<a href="/wiki/Carbon" title="Carbon">C</a>O<sub>2</sub>)</li> <li><a href="/wiki/Carbon_trioxide" title="Carbon trioxide">Carbon trioxide</a> (<a href="/wiki/Carbon" title="Carbon">C</a>O<sub>3</sub>)</li> <li><a href="/wiki/Cerium(IV)_oxide" title="Cerium(IV) oxide">Cerium(IV) oxide</a> (<a href="/wiki/Cerium" title="Cerium">Ce</a>O<sub>2</sub>)</li> <li><a href="/wiki/Chlorine_dioxide" title="Chlorine dioxide">Chlorine dioxide</a> (<a href="/wiki/Chlorine" title="Chlorine">Cl</a>O<sub>2</sub>)</li> <li><a href="/wiki/Chromium(IV)_oxide" title="Chromium(IV) oxide">Chromium(IV) oxide</a> (<a href="/wiki/Chromium" title="Chromium">Cr</a>O<sub>2</sub>)</li> <li><a href="/wiki/Curium(IV)_oxide" title="Curium(IV) oxide">Curium(IV) oxide</a> (<a href="/wiki/Curium" title="Curium">Cm</a>O<sub>2</sub>)</li> <li><a href="/wiki/Dinitrogen_tetroxide" title="Dinitrogen tetroxide">Dinitrogen tetroxide</a> (<a href="/wiki/Nitrogen" title="Nitrogen">N</a><sub>2</sub>O<sub>4</sub>)</li> <li><a href="/wiki/Germanium_dioxide" title="Germanium dioxide">Germanium dioxide</a> (<a href="/wiki/Germanium" title="Germanium">Ge</a>O<sub>2</sub>)</li> <li><a href="/wiki/Iodine_dioxide" title="Iodine dioxide">Iodine dioxide</a> (<a href="/wiki/Iodine" title="Iodine">I</a>O<sub>2</sub>)</li> <li><a href="/wiki/Iridium_dioxide" class="mw-redirect" title="Iridium dioxide">Iridium dioxide</a> (<a href="/wiki/Iridium" title="Iridium">Ir</a>O<sub>2</sub>)</li> <li><a href="/wiki/Hafnium(IV)_oxide" title="Hafnium(IV) oxide">Hafnium(IV) oxide</a> (<a href="/wiki/Hafnium" title="Hafnium">Hf</a>O<sub>2</sub>)</li> <li><a href="/wiki/Lead_dioxide" title="Lead dioxide">Lead dioxide</a> (<a href="/wiki/Lead" title="Lead">Pb</a>O<sub>2</sub>)</li> <li><a href="/wiki/Manganese_dioxide" title="Manganese dioxide">Manganese dioxide</a> (<a href="/wiki/Manganese" title="Manganese">Mn</a>O<sub>2</sub>)</li> <li><a href="/wiki/Molybdenum_dioxide" title="Molybdenum dioxide">Molybdenum dioxide</a> (<a href="/wiki/Molybdenum" title="Molybdenum">Mo</a>O<sub>2</sub>)</li> <li><a href="/wiki/Neptunium(IV)_oxide" title="Neptunium(IV) oxide">Neptunium(IV) oxide</a> (<a href="/wiki/Neptunium" title="Neptunium">Np</a>O<sub>2</sub>)</li> <li><a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">Nitrogen dioxide</a> (<a href="/wiki/Nitrogen" title="Nitrogen">N</a>O<sub>2</sub>)</li> <li><a href="/wiki/Niobium_dioxide" title="Niobium dioxide">Niobium dioxide</a> (<a href="/wiki/Niobium" title="Niobium">Nb</a>O<sub>2</sub>)</li> <li><a href="/wiki/Osmium_dioxide" title="Osmium dioxide">Osmium dioxide</a> (<a href="/wiki/Osmium" title="Osmium">Os</a>O<sub>2</sub>)</li> <li><a href="/wiki/Platinum_dioxide" class="mw-redirect" title="Platinum dioxide">Platinum dioxide</a> (<a href="/wiki/Platinum" title="Platinum">Pt</a>O<sub>2</sub>)</li> <li><a href="/wiki/Plutonium(IV)_oxide" title="Plutonium(IV) oxide">Plutonium(IV) oxide</a> (<a href="/wiki/Plutonium" title="Plutonium">Pu</a>O<sub>2</sub>)</li> <li><a href="/wiki/Polonium_dioxide" title="Polonium dioxide">Polonium dioxide</a> (<a href="/wiki/Polonium" title="Polonium">Po</a>O<sub>2</sub>)</li> <li><a href="/wiki/Praseodymium(IV)_oxide" title="Praseodymium(IV) oxide">Praseodymium(IV) oxide</a> (<a href="/wiki/Praseodymium" title="Praseodymium">Pr</a>O<sub>2</sub>)</li> <li><a href="/wiki/Protactinium(IV)_oxide" title="Protactinium(IV) oxide">Protactinium(IV) oxide</a> (<a href="/wiki/Protactinium" title="Protactinium">Pa</a>O<sub>2</sub>)</li> <li><a href="/wiki/Rhenium(IV)_oxide" title="Rhenium(IV) oxide">Rhenium(IV) oxide</a> (<a href="/wiki/Rhenium" title="Rhenium">Re</a>O<sub>2</sub>)</li> <li><a href="/wiki/Rhodium(IV)_oxide" title="Rhodium(IV) oxide">Rhodium(IV) oxide</a> (<a href="/wiki/Rhodium" title="Rhodium">Rh</a>O<sub>2</sub>)</li> <li><a href="/wiki/Ruthenium(IV)_oxide" title="Ruthenium(IV) oxide">Ruthenium(IV) oxide</a> (<a href="/wiki/Ruthenium" title="Ruthenium">Ru</a>O<sub>2</sub>)</li> <li><a href="/wiki/Selenium_dioxide" title="Selenium dioxide">Selenium dioxide</a> (<a href="/wiki/Selenium" title="Selenium">Se</a>O<sub>2</sub>)</li> <li><a href="/wiki/Silicon_dioxide" title="Silicon dioxide">Silicon dioxide</a> (<a href="/wiki/Silicon" title="Silicon">Si</a>O<sub>2</sub>)</li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a> (<a href="/wiki/Sulfur" title="Sulfur">S</a>O<sub>2</sub>)</li> <li><a href="/wiki/Technetium(IV)_oxide" title="Technetium(IV) oxide">Technetium(IV) oxide</a> (<a href="/wiki/Technetium" title="Technetium">Tc</a>O<sub>2</sub>)</li> <li><a href="/wiki/Tellurium_dioxide" title="Tellurium dioxide">Tellurium dioxide</a> (<a href="/wiki/Tellurium" title="Tellurium">Te</a>O<sub>2</sub>)</li> <li><a href="/wiki/Terbium(IV)_oxide" title="Terbium(IV) oxide">Terbium(IV) oxide</a> (<a href="/wiki/Terbium" title="Terbium">Tb</a>O<sub>2</sub>)</li> <li><a href="/wiki/Thorium_dioxide" title="Thorium dioxide">Thorium dioxide</a> (<a href="/wiki/Thorium" title="Thorium">Th</a>O<sub>2</sub>)</li> <li><a href="/wiki/Tin(IV)_oxide" title="Tin(IV) oxide">Tin dioxide</a> (<a href="/wiki/Tin" title="Tin">Sn</a>O<sub>2</sub>)</li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a> (<a href="/wiki/Titanium" title="Titanium">Ti</a>O<sub>2</sub>)</li> <li><a href="/wiki/Tungsten(IV)_oxide" title="Tungsten(IV) oxide">Tungsten(IV) oxide</a> (<a href="/wiki/Tungsten" title="Tungsten">W</a>O<sub>2</sub>)</li> <li><a href="/wiki/Uranium_dioxide" title="Uranium dioxide">Uranium dioxide</a> (<a href="/wiki/Uranium" title="Uranium">U</a>O<sub>2</sub>)</li> <li><a href="/wiki/Vanadium(IV)_oxide" title="Vanadium(IV) oxide">Vanadium(IV) oxide</a> (<a href="/wiki/Vanadium" title="Vanadium">V</a>O<sub>2</sub>)</li> <li><a href="/wiki/Zirconium_dioxide" title="Zirconium dioxide">Zirconium dioxide</a> (<a href="/wiki/Zirconium" title="Zirconium">Zr</a>O<sub>2</sub>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">+5 oxidation state</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antimony_pentoxide" title="Antimony pentoxide">Antimony pentoxide</a> (<a href="/wiki/Antimony" title="Antimony">Sb</a><sub>2</sub>O<sub>5</sub>)</li> <li><a href="/wiki/Arsenic_pentoxide" title="Arsenic pentoxide">Arsenic pentoxide</a> (<a href="/wiki/Arsenic" title="Arsenic">As</a><sub>2</sub>O<sub>5</sub>)</li> <li><a href="/wiki/Bismuth_pentoxide" title="Bismuth pentoxide">Bismuth pentoxide</a> (<a href="/wiki/Bismuth" title="Bismuth">Bi</a><sub>2</sub>O<sub>5</sub>)</li> <li><a href="/wiki/Dinitrogen_pentoxide" title="Dinitrogen pentoxide">Dinitrogen pentoxide</a> (<a href="/wiki/Nitrogen" title="Nitrogen">N</a><sub>2</sub>O<sub>5</sub>)</li> <li><a href="/wiki/Niobium_pentoxide" title="Niobium pentoxide">Niobium pentoxide</a> (<a href="/wiki/Niobium" title="Niobium">Nb</a><sub>2</sub>O<sub>5</sub>)</li> <li><a href="/wiki/Phosphorus_pentoxide" title="Phosphorus pentoxide">Phosphorus pentoxide</a> (<a href="/wiki/Phosphorus" title="Phosphorus">P</a><sub>2</sub>O<sub>5</sub>)</li> <li><a href="/wiki/Protactinium(V)_oxide" title="Protactinium(V) oxide">Protactinium(V) oxide</a> (<a href="/wiki/Protactinium" title="Protactinium">Pa</a><sub>2</sub>O<sub>5</sub>)</li> <li><a href="/wiki/Tantalum_pentoxide" title="Tantalum pentoxide">Tantalum pentoxide</a> (<a href="/wiki/Tantalum" title="Tantalum">Ta</a><sub>2</sub>O<sub>5</sub>)</li> <li><a href="/wiki/Tungsten_pentoxide" title="Tungsten pentoxide">Tungsten pentoxide</a> (<a href="/wiki/Tungsten" title="Tungsten">W</a><sub>2</sub>O<sub>5</sub>)</li> <li><a href="/wiki/Vanadium(V)_oxide" title="Vanadium(V) oxide">Vanadium(V) oxide</a> (<a href="/wiki/Vanadium" title="Vanadium">V</a><sub>2</sub>O<sub>5</sub>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">+6 oxidation state</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chromium_trioxide" title="Chromium trioxide">Chromium trioxide</a> (<a href="/wiki/Chromium" title="Chromium">Cr</a>O<sub>3</sub>)</li> <li><a href="/wiki/Molybdenum_trioxide" title="Molybdenum trioxide">Molybdenum trioxide</a> (<a href="/wiki/Molybdenum" title="Molybdenum">Mo</a>O<sub>3</sub>)</li> <li><a href="/wiki/Polonium_trioxide" title="Polonium trioxide">Polonium trioxide</a> (<a href="/wiki/Polonium" title="Polonium">Po</a>O<sub>3</sub>)</li> <li><a href="/wiki/Rhenium_trioxide" title="Rhenium trioxide">Rhenium trioxide</a> (<a href="/wiki/Rhenium" title="Rhenium">Re</a>O<sub>3</sub>)</li> <li><a href="/wiki/Selenium_trioxide" title="Selenium trioxide">Selenium trioxide</a> (<a href="/wiki/Selenium" title="Selenium">Se</a>O<sub>3</sub>)</li> <li><a href="/wiki/Sulfur_trioxide" title="Sulfur trioxide">Sulfur trioxide</a> (<a href="/wiki/Sulfur" title="Sulfur">S</a>O<sub>3</sub>)</li> <li><a href="/wiki/Tellurium_trioxide" title="Tellurium trioxide">Tellurium trioxide</a> (<a href="/wiki/Tellurium" title="Tellurium">Te</a>O<sub>3</sub>)</li> <li><a href="/wiki/Tungsten_trioxide" title="Tungsten trioxide">Tungsten trioxide</a> (<a href="/wiki/Tungsten" title="Tungsten">W</a>O<sub>3</sub>)</li> <li><a href="/wiki/Uranium_trioxide" title="Uranium trioxide">Uranium trioxide</a> (<a href="/wiki/Uranium" title="Uranium">U</a>O<sub>3</sub>)</li> <li><a href="/wiki/Xenon_trioxide" title="Xenon trioxide">Xenon trioxide</a> (<a href="/wiki/Xenon" title="Xenon">Xe</a>O<sub>3</sub>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">+7 oxidation state</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dichlorine_heptoxide" title="Dichlorine heptoxide">Dichlorine heptoxide</a> (<a href="/wiki/Chlorine" title="Chlorine">Cl</a><sub>2</sub>O<sub>7</sub>)</li> <li><a href="/wiki/Manganese_heptoxide" title="Manganese heptoxide">Manganese heptoxide</a> (<a href="/wiki/Manganese" title="Manganese">Mn</a><sub>2</sub>O<sub>7</sub>)</li> <li><a href="/wiki/Rhenium(VII)_oxide" title="Rhenium(VII) oxide">Rhenium(VII) oxide</a> (<a href="/wiki/Rhenium" title="Rhenium">Re</a><sub>2</sub>O<sub>7</sub>)</li> <li><a href="/wiki/Technetium(VII)_oxide" title="Technetium(VII) oxide">Technetium(VII) oxide</a> (<a href="/wiki/Technetium" title="Technetium">Tc</a><sub>2</sub>O<sub>7</sub>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">+8 oxidation state</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Iridium_tetroxide" title="Iridium tetroxide">Iridium tetroxide</a> (<a href="/wiki/Iridium" title="Iridium">Ir</a>O<sub>4</sub>)</li> <li><a href="/wiki/Osmium_tetroxide" title="Osmium tetroxide">Osmium tetroxide</a> (<a href="/wiki/Osmium" title="Osmium">Os</a>O<sub>4</sub>)</li> <li><a href="/wiki/Ruthenium_tetroxide" title="Ruthenium tetroxide">Ruthenium tetroxide</a> (<a href="/wiki/Ruthenium" title="Ruthenium">Ru</a>O<sub>4</sub>)</li> <li><a href="/wiki/Xenon_tetroxide" title="Xenon tetroxide">Xenon tetroxide</a> (<a href="/wiki/Xenon" title="Xenon">Xe</a>O<sub>4</sub>)</li> <li><a href="/wiki/Hassium_tetroxide" title="Hassium tetroxide">Hassium tetroxide</a> (<a href="/wiki/Hassium" title="Hassium">Hs</a>O<sub>4</sub>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oxocarbon" title="Oxocarbon">Oxocarbon</a></li> <li><a href="/wiki/Suboxide" title="Suboxide">Suboxide</a></li> <li><a href="/wiki/Oxyanion" title="Oxyanion">Oxyanion</a></li> <li><a href="/wiki/Ozonide" title="Ozonide">Ozonide</a></li> <li><a href="/wiki/Peroxide" title="Peroxide">Peroxide</a></li> <li><a href="/wiki/Superoxide" title="Superoxide">Superoxide</a></li> <li><a href="/wiki/Oxypnictide" title="Oxypnictide">Oxypnictide</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>Oxides are sorted by <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation state</a>. <a href="/wiki/Category:Oxides" 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