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data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Cyanate_ion" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Cyanate_ion"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Cyanate ion</span> </div> </a> <ul id="toc-Cyanate_ion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyanate_salts" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Cyanate_salts"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Cyanate salts</span> </div> </a> <ul id="toc-Cyanate_salts-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Complexes_with_the_cyanate_ion" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Complexes_with_the_cyanate_ion"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Complexes with the cyanate ion</span> </div> </a> <ul id="toc-Complexes_with_the_cyanate_ion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyanate_functional_group" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Cyanate_functional_group"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Cyanate functional group</span> </div> </a> <ul id="toc-Cyanate_functional_group-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bibliography" class="vector-toc-list-item vector-toc-level-1 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Available in 31 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-31" 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">31 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D9%8A%D8%A7%D9%86%D8%A7%D8%AA" title="سيانات – Arabic" lang="ar" hreflang="ar" data-title="سيانات" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Cianat" title="Cianat – Catalan" lang="ca" hreflang="ca" data-title="Cianat" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kyanatany" title="Kyanatany – Czech" lang="cs" hreflang="cs" data-title="Kyanatany" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Cyanat" title="Cyanat – Danish" lang="da" hreflang="da" data-title="Cyanat" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de badge-Q70894304 mw-list-item" title=""><a href="https://de.wikipedia.org/wiki/Cyanate" title="Cyanate – German" lang="de" hreflang="de" data-title="Cyanate" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Cianato" title="Cianato – Spanish" lang="es" hreflang="es" data-title="Cianato" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Cianatoj" title="Cianatoj – Esperanto" lang="eo" hreflang="eo" data-title="Cianatoj" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%DB%8C%D8%A7%D9%86%D8%A7%D8%AA" title="سیانات – Persian" lang="fa" hreflang="fa" data-title="سیانات" 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/Cyanate" title="Cyanate – French" lang="fr" hreflang="fr" data-title="Cyanate" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Cian%C3%A1it" title="Cianáit – Irish" lang="ga" hreflang="ga" data-title="Cianáit" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B8%E0%A4%BE%E0%A4%AF%E0%A4%A8%E0%A5%87%E0%A4%9F" title="सायनेट – Hindi" lang="hi" hreflang="hi" data-title="सायनेट" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Sianat" title="Sianat – Indonesian" lang="id" hreflang="id" data-title="Sianat" 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/Cianato" title="Cianato – Italian" lang="it" hreflang="it" data-title="Cianato" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Cyanatum" title="Cyanatum – Latin" lang="la" hreflang="la" data-title="Cyanatum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Cian%C4%81ti" title="Cianāti – Latvian" lang="lv" hreflang="lv" data-title="Cianāti" 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/Cian%C3%A1t" title="Cianát – Hungarian" lang="hu" hreflang="hu" data-title="Cianát" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cyanaat" title="Cyanaat – Dutch" lang="nl" hreflang="nl" data-title="Cyanaat" 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/%E3%82%B7%E3%82%A2%E3%83%8D%E3%83%BC%E3%83%88" title="シアネート – Japanese" lang="ja" hreflang="ja" data-title="シアネート" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Cyanat" title="Cyanat – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Cyanat" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%B8%E0%A8%BE%E0%A8%87%E0%A8%86%E0%A8%A8%E0%A9%87%E0%A8%9F" title="ਸਾਇਆਨੇਟ – Punjabi" lang="pa" hreflang="pa" data-title="ਸਾਇਆਨੇਟ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Cyjaniany" title="Cyjaniany – Polish" lang="pl" hreflang="pl" data-title="Cyjaniany" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Cianato" title="Cianato – Portuguese" lang="pt" hreflang="pt" data-title="Cianato" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Cianat" title="Cianat – Romanian" lang="ro" hreflang="ro" data-title="Cianat" 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%A6%D0%B8%D0%B0%D0%BD%D0%B0%D1%82%D1%8B" title="Цианаты – Russian" lang="ru" hreflang="ru" data-title="Цианаты" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyanatan" title="Kyanatan – Slovak" lang="sk" hreflang="sk" data-title="Kyanatan" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Cijanat" title="Cijanat – Serbian" lang="sr" hreflang="sr" data-title="Cijanat" 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/Cijanat" title="Cijanat – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cijanat" 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/Syanaatti" title="Syanaatti – Finnish" lang="fi" hreflang="fi" data-title="Syanaatti" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Cyanater" title="Cyanater – Swedish" lang="sv" hreflang="sv" data-title="Cyanater" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A6%D1%96%D0%B0%D0%BD%D0%B0%D1%82%D0%B8" title="Ціанати – Ukrainian" lang="uk" hreflang="uk" data-title="Ціанати" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%B0%B0%E9%85%B8%E7%9B%90" title="氰酸盐 – Chinese" lang="zh" hreflang="zh" data-title="氰酸盐" 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/Q843438#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div 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data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Anion with formula OCN and charge –1</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Fulminate" title="Fulminate">fulminate</a>.</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Cyanate-ion-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Cyanate-ion-3D-vdW.png/200px-Cyanate-ion-3D-vdW.png" decoding="async" width="200" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Cyanate-ion-3D-vdW.png/300px-Cyanate-ion-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Cyanate-ion-3D-vdW.png/400px-Cyanate-ion-3D-vdW.png 2x" data-file-width="1100" data-file-height="703" /></a><figcaption><a href="/wiki/Space-filling_model" title="Space-filling model">Space-filling model</a> of the cyanate anion</figcaption></figure> <p>The <b>cyanate ion</b> is an <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical 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">OCN<sup class="template-chem2-sup">−</sup></span>. It is a <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">resonance</a> of three forms: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[O<sup class="template-chem2-sup">−</sup>−C≡N]</span> (61%) ↔ <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[O=C=N<sup class="template-chem2-sup">−</sup>]</span> (30%) ↔ <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[O<sup class="template-chem2-sup">+</sup>≡C−N<sup>2−</sup>]</span> (4%). </p><p>Cyanate is the derived anion of <a href="/wiki/Isocyanic_acid" title="Isocyanic acid">isocyanic acid</a>, H−N=C=O, and its lesser <a href="/wiki/Tautomer" title="Tautomer">tautomer</a> cyanic acid (a.k.a. cyanol), H−O−C≡N. </p><p>Any salt containing the ion, such as <a href="/wiki/Ammonium_cyanate" title="Ammonium cyanate">ammonium cyanate</a>, is called a cyanate. </p><p>The cyanate ion is an <a href="/wiki/Isomer" title="Isomer">isomer</a> of the much-less-stable <a href="/wiki/Fulminate" title="Fulminate">fulminate</a> anion, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CNO<sup class="template-chem2-sup">−</sup></span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[C<sup class="template-chem2-sup">−</sup>≡N<sup class="template-chem2-sup">+</sup>−O<sup class="template-chem2-sup">−</sup>]</span>.<sup id="cite_ref-mart2019_1-0" class="reference"><a href="#cite_note-mart2019-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>The cyanate ion is an <a href="/wiki/Ambidentate_ligand" class="mw-redirect" title="Ambidentate ligand">ambidentate ligand</a>, forming <a href="/wiki/Coordination_complex" title="Coordination complex">complexes</a> with a metal ion in which either the nitrogen or oxygen atom may be the <a href="/wiki/Electron_donor" title="Electron donor">electron-pair donor</a>. It can also act as a <a href="/wiki/Bridging_ligand" title="Bridging ligand">bridging ligand</a>. </p><p>Compounds that contain the <b>cyanate <a href="/wiki/Functional_group" title="Functional group">functional group</a></b>, −O−C≡N, are known as cyanates or <a href="/wiki/Cyanate_ester" title="Cyanate ester">cyanate esters</a>. The cyanate functional group is distinct from the <a href="/wiki/Isocyanate" title="Isocyanate">isocyanate</a> functional group, −N=C=O; the <a href="/wiki/Fulminate" title="Fulminate">fulminate</a> functional group, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−O−N<sup class="template-chem2-sup">+</sup>≡C<sup class="template-chem2-sup">−</sup></span>; and the <a href="/wiki/Nitrile_oxide" class="mw-redirect" title="Nitrile oxide">nitrile oxide</a> functional group, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CNO</span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C≡N<sup class="template-chem2-sup">+</sup>−O<sup class="template-chem2-sup">−</sup></span>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Cyanate_ion">Cyanate ion</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanate&action=edit&section=1" title="Edit section: Cyanate ion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The three atoms in a cyanate ion lie on a straight line, giving the ion a linear structure. The <a href="/wiki/Electronic_structure" class="mw-redirect" title="Electronic structure">electronic structure</a> is described most simply as </p> <dl><dd>:Ö̤−C≡N:</dd></dl> <p>with a single C−O bond and a triple C≡N bond. (Or more completely as :Ö̤−C≡N: ↔ Ö̤=C=N̤̈ ↔ :O≡C−N̤̈:) The <a href="/wiki/Infrared_spectrum" class="mw-redirect" title="Infrared spectrum">infrared spectrum</a> of a cyanate salt has a band at ca. 2096 cm<sup>−1</sup>; such a high frequency is characteristic of a <a href="/wiki/Triple_bond" title="Triple bond">triple bond</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>The cyanate ion is a <a href="/wiki/Lewis_base" class="mw-redirect" title="Lewis base">Lewis base</a>. Both the oxygen and nitrogen atoms carry a <a href="/wiki/Lone_pair" title="Lone pair">lone pair</a> of electrons and either one, the other, or both can be donated to <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a> acceptors. It can be described as an <a href="/wiki/Ambidentate_ligand" class="mw-redirect" title="Ambidentate ligand">ambidentate ligand</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Cyanate_salts">Cyanate salts</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanate&action=edit&section=2" title="Edit section: Cyanate salts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Sodium_cyanate" title="Sodium cyanate">Sodium cyanate</a> is <a href="/wiki/Isostructural" title="Isostructural">isostructural</a> with sodium <a href="/wiki/Fulminate" title="Fulminate">fulminate</a>, confirming the linear structure of the cyanate ion.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is made industrially by heating a mixture of <a href="/wiki/Sodium_carbonate" title="Sodium carbonate">sodium carbonate</a> and <a href="/wiki/Urea" title="Urea">urea</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Na<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">3</sub> + 2 OC(NH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">2</sub> → 2 NaNCO + CO<sub class="template-chem2-sub">2</sub> + 2 NH<sub class="template-chem2-sub">3</sub> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>A similar reaction is used to make <a href="/wiki/Potassium_cyanate" title="Potassium cyanate">potassium cyanate</a>. Cyanates are produced when <a href="/wiki/Cyanide" title="Cyanide">cyanides</a> are oxidized. Use of this fact is made in cyanide decontamination processes where oxidants such as <a href="/wiki/Permanganate" title="Permanganate">permanganate</a> and <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> are used to convert toxic cyanide into less-toxic cyanate. </p> <table class="wikitable"> <tbody><tr> <th>Name </th> <th>formula </th> <th>Crystal system </th> <th>Space group </th> <th>Unit cell (Å) </th> <th>volume (Å<sup>3</sup>) </th> <th>Density (g/cm<sup>3</sup>) </th> <th>Comment </th> <th>Reference </th></tr> <tr> <td><a href="/wiki/Ammonium_cyanate" title="Ammonium cyanate">Ammonium cyanate</a> </td> <td>NH<sub>4</sub>OCN </td> <td>tetragonal </td> <td>P4/nmm </td> <td><i>a</i>=5.082 <i>b</i>=5.082 <i>c</i>=5.551 </td> <td> </td> <td> </td> <td>decomposes when heated to <a href="/wiki/Urea" title="Urea">urea</a> </td> <td><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/w/index.php?title=Lithium_cyanate&action=edit&redlink=1" class="new" title="Lithium cyanate (page does not exist)">Lithium cyanate</a> </td> <td>LiOCN </td> <td>trigonal </td> <td><i>R</i><span style="text-decoration:overline;">3</span><i>m</i> </td> <td><i>a</i> = 3.230 <i>b</i> = 14.268 Z=3 </td> <td>128.90 </td> <td>1.895 </td> <td>melts at 475 °C </td> <td><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Sodium_cyanate" title="Sodium cyanate">Sodium cyanate</a> </td> <td>NaOCN </td> <td>hexagonal </td> <td><i>R</i><span style="text-decoration:overline;">3</span><i>m</i> </td> <td><i>a</i> = 3.568 <i>c</i> = 15.123 </td> <td>166.72 </td> <td>1.94 </td> <td>melts at 550 °C </td> <td><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Potassium_cyanate" title="Potassium cyanate">Potassium cyanate</a> </td> <td>KOCN </td> <td>tetragonal </td> <td><i>I</i>4/<i>mcm</i> </td> <td><i>a</i> = 6.091 <i>c</i> = 7.052 </td> <td>261.6 </td> <td>2.056 </td> <td>melts at 315 °C </td> <td><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/w/index.php?title=Rubidium_cyanate&action=edit&redlink=1" class="new" title="Rubidium cyanate (page does not exist)">Rubidium cyanate</a> </td> <td>RbOCN </td> <td>tetragonal </td> <td><i>I</i>4/<i>mcm</i> </td> <td><i>a</i> = 6.35 <i>c</i> = 7.38 </td> <td>297.58 </td> <td>2.85 </td> <td> </td> <td><sup id="cite_ref-inorg_9-0" class="reference"><a href="#cite_note-inorg-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/w/index.php?title=Cesium_cyanate&action=edit&redlink=1" class="new" title="Cesium cyanate (page does not exist)">Cesium cyanate</a> </td> <td>CsOCN </td> <td>tetragonal </td> <td><i>I</i>4<i>mcm</i> </td> <td><i>a</i> = 6.519 <i>c</i> = 7.994 </td> <td>339.68 </td> <td>3.42 </td> <td> </td> <td><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/w/index.php?title=Thallium_cyanate&action=edit&redlink=1" class="new" title="Thallium cyanate (page does not exist)">Thallium cyanate</a> </td> <td>TlOCN </td> <td>tetragonal </td> <td><i>I</i>4<i>mcm</i> </td> <td><i>a</i> = 6.23 <i>c</i> = 7.32 </td> <td>284.3 </td> <td>5.76 </td> <td> </td> <td><sup id="cite_ref-inorg_9-1" class="reference"><a href="#cite_note-inorg-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Silver_cyanate" title="Silver cyanate">Silver cyanate</a> </td> <td>AgOCN </td> <td>monoclinic </td> <td><i>P</i>2<sub>1</sub>/<i>m</i> </td> <td><i>a</i> = 5.474 <i>b</i> = 6.378 <i>c</i> = 3.417 <i>β</i> = 90.931° </td> <td>119.29 </td> <td>4.173 </td> <td>melts at 652 °C </td> <td><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/w/index.php?title=Strontium_cyanate&action=edit&redlink=1" class="new" title="Strontium cyanate (page does not exist)">Strontium cyanate</a> </td> <td>Sr(OCN)<sub>2</sub> </td> <td>orthorhombic </td> <td><i>Fddd</i> </td> <td><i>a</i> = 6.151 <i>b</i> = 11.268 <i>c</i> = 11.848 Z = 8 </td> <td>821.1 </td> <td>2.78 </td> <td> </td> <td><sup id="cite_ref-Sreu_12-0" class="reference"><a href="#cite_note-Sreu-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="Complexes_with_the_cyanate_ion">Complexes with the cyanate ion</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanate&action=edit&section=3" title="Edit section: Complexes with the cyanate ion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanate is an <a href="/wiki/Ambidentate_ligand" class="mw-redirect" title="Ambidentate ligand">ambidentate ligand</a> which can donate the pair of electrons on the nitrogen atom or the oxygen atom, or both. Structurally the isomers can be distinguished by the geometry of the complex. In <i>N</i>-bonded cyanate complexes the M−NCO unit sometimes has a linear structure, but with <i>O</i>-bonded cyanate the M−O−C unit is bent. Thus, the silver cyanato complex, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Ag(NCO)<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">−</sup></span>, has a linear structure as shown by <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a>.<sup id="cite_ref-ChemicalElements_13-0" class="reference"><a href="#cite_note-ChemicalElements-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> However, the crystal structure of <a href="/wiki/Silver_cyanate" title="Silver cyanate">silver cyanate</a> shows zigzag chains of nitrogen atoms and silver atoms.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> There also exists a structure </p> <pre> NCO / \ Ni Ni \ / OCN </pre> <p>in which the Ni-N-C group is bent.<sup id="cite_ref-ChemicalElements_13-1" class="reference"><a href="#cite_note-ChemicalElements-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">Infrared spectroscopy</a> has been used extensively to distinguish between isomers. Many complexes of <a href="/wiki/Divalent" class="mw-redirect" title="Divalent">divalent</a> metals are <i>N</i>-bonded. <i>O</i>-Bonding has been suggested for complexes of the type <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[M(OCN)<sub class="template-chem2-sub">6</sub>]<sup class="template-chem2-sup"><i>n</i>−</sup></span>, M = Mo(III), Re(IV), and Re(V). The yellow complex <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Rh(<a href="/wiki/Triphenylphosphine" title="Triphenylphosphine">PPh<sub class="template-chem2-sub">3</sub></a>)<sub class="template-chem2-sub">3</sub>(NCO)</span> and orange complex <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Rh(<a href="/wiki/Triphenylphosphine" title="Triphenylphosphine">PPh<sub class="template-chem2-sub">3</sub></a>)<sub class="template-chem2-sub">3</sub>(OCN)</span> are <a href="/wiki/Linkage_isomerism" title="Linkage isomerism">linkage isomers</a> and show differences in their infrared spectra which can be used for diagnosis.<sup id="cite_ref-cno_15-0" class="reference"><a href="#cite_note-cno-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>The cyanate ion can bridge between two metal atoms by using both its donor atoms. For example, this structure is found in the compound <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Ni<sub class="template-chem2-sub">2</sub>(NCO)<sub class="template-chem2-sub">2</sub>(<a href="/wiki/Ethylene_diamine" class="mw-redirect" title="Ethylene diamine">En</a>)<sub class="template-chem2-sub">2</sub>](<a href="/wiki/Tetraphenylborate" title="Tetraphenylborate">BPh<sub class="template-chem2-sub">4</sub></a>)<sub class="template-chem2-sub">2</sub></span>. In this compound both the Ni−N−C unit and Ni−O−C unit are bent, even though in the first case donation is through the nitrogen atom.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Cyanate_functional_group">Cyanate functional group</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanate&action=edit&section=4" title="Edit section: Cyanate functional group"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Compounds that contain the cyanate <a href="/wiki/Functional_group" title="Functional group">functional group</a>, −O−C≡N, are known as cyanates or <a href="/wiki/Cyanate_ester" title="Cyanate ester">cyanate esters</a>. <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> cyanates such are phenyl cyanate, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OCN</span> can be formed by a reaction of <a href="/wiki/Phenol" title="Phenol">phenol</a> with <a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">cyanogen chloride</a>, ClCN, in the presence of a base. </p><p><a href="/wiki/Organic_compound" title="Organic compound">Organic compounds</a> that contain the isocyanate <a href="/wiki/Functional_group" title="Functional group">functional group</a> −N=C=O are known as <a href="/wiki/Isocyanate" title="Isocyanate">isocyanates</a>. It is conventional in <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a> to write isocyanates with two double bonds, which accords with a simplistic <a href="/wiki/Valence_bond_theory" title="Valence bond theory">valence bond theory</a> of the bonding. In <a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">nucleophilic substitution</a> reactions cyanate usually forms an isocyanate. Isocyanates are widely used in the manufacture of <a href="/wiki/Polyurethane" title="Polyurethane">polyurethane</a><sup id="cite_ref-Seymour_17-0" class="reference"><a href="#cite_note-Seymour-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> products and <a href="/wiki/Pesticide" title="Pesticide">pesticides</a>; <a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">methyl isocyanate</a>, used to make pesticides, was a major factor in the <a href="/wiki/Bhopal_disaster" title="Bhopal disaster">Bhopal disaster</a>. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanate&action=edit&section=5" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Cyanide" title="Cyanide">Cyanide</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CN<sup class="template-chem2-sup">−</sup></span> and <a href="/wiki/Nitrile" title="Nitrile">nitrile</a> group, −C≡N</li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isocyanide</a> or isonitrile group, −N≡C</li> <li><a href="/wiki/Thiocyanate" title="Thiocyanate">Thiocyanate</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">SCN<sup class="template-chem2-sup">−</sup></span>, −S−C≡N</li> <li><a href="/wiki/Selenocyanate" title="Selenocyanate">Selenocyanate</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">SeCN<sup class="template-chem2-sup">−</sup></span>, −Se−C≡N</li> <li><a href="/w/index.php?title=Tellurocyanate&action=edit&redlink=1" class="new" title="Tellurocyanate (page does not exist)">Tellurocyanate</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">TeCN<sup class="template-chem2-sup">−</sup></span>, −Te−C≡N</li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a> group, −N=C=O</li> <li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a> group, −N=C=S</li> <li><a href="/w/index.php?title=Isoselenocyanate&action=edit&redlink=1" class="new" title="Isoselenocyanate (page does not exist)">Isoselenocyanate</a> group, −N=C=Se</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanate&action=edit&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-mart2019-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-mart2019_1-0">^</a></b></span> <span class="reference-text">William R. 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Fulminates of acetylene, ethylene, and allene". <i>Journal of Energetic Materials</i>, volume 31, issue 7, pages 70-79. <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F07370652.2018.1531089">10.1080/07370652.2018.1531089</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">Nakamoto, Part A, p171</span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text">Wells, p722.</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">Greenwood, p324</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="CITEREFMacLean,_Elizabeth_J.Harris,_Kenneth_D._M.Kariuki,_Benson_M.Kitchin,_Simon_J.2003" class="citation journal cs1">MacLean, Elizabeth J.; Harris, Kenneth D. 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DiSalvo (2020). <a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fznb-2019-0168">"Structural characterization and Raman spectrum of Cs[OCN]"</a>. <i>Zeitschrift für Naturforschung B</i>. <b>75</b> (<span class="nowrap">1–</span>2): <span class="nowrap">129–</span>133. <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/10.1515%2Fznb-2019-0168">10.1515/znb-2019-0168</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Zeitschrift+f%C3%BCr+Naturforschung+B&rft.atitle=Structural+characterization+and+Raman+spectrum+of+Cs%5BOCN%5D&rft.volume=75&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E129-%3C%2Fspan%3E133&rft.date=2020&rft_id=info%3Adoi%2F10.1515%2Fznb-2019-0168&rft.au=Olaf+Reckeweg&rft.au=Armin+Schulz&rft.au=Francis+J.+DiSalvo&rft_id=https%3A%2F%2Fdoi.org%2F10.1515%252Fznb-2019-0168&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanate" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFD.J._WilliamsS.C._VogelL.L._Daemen2006" class="citation journal cs1 cs1-prop-long-vol">D.J. Williams; S.C. Vogel; L.L. Daemen (2006). "Neutron diffraction study of cyanate ligand order/disorder in AgNCO at 300–50K". <i>Physica B: Condensed Matter</i>. <span class="nowrap">385–</span>386 (1): <span class="nowrap">228–</span>230. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.physb.2006.05.197">10.1016/j.physb.2006.05.197</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Physica+B%3A+Condensed+Matter&rft.atitle=Neutron+diffraction+study+of+cyanate+ligand+order%2Fdisorder+in+AgNCO+at+300%E2%80%9350K&rft.volume=385-386&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E228-%3C%2Fspan%3E230&rft.date=2006&rft_id=info%3Adoi%2F10.1016%2Fj.physb.2006.05.197&rft.au=D.J.+Williams&rft.au=S.C.+Vogel&rft.au=L.L.+Daemen&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanate" class="Z3988"></span></span> </li> <li id="cite_note-Sreu-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-Sreu_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSandro_PaganoGiuseppe_MontanaClaudia_WicklederWolfgang_Schnick2009" class="citation journal cs1">Sandro Pagano; Giuseppe Montana; Claudia Wickleder; Wolfgang Schnick (2009). <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fchem.200900053">"Urea Route to Homoleptic Cyanates—Characterization and Luminescence Properties of [M(OCN)2(urea)] and M(OCN)2 with M=Sr, Eu"</a>. <i>Chemistry: A European Journal</i>. <b>15</b> (25): <span class="nowrap">6186–</span>6193. <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/10.1002%2Fchem.200900053">10.1002/chem.200900053</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19444832">19444832</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemistry%3A+A+European+Journal&rft.atitle=Urea+Route+to+Homoleptic+Cyanates%E2%80%94Characterization+and+Luminescence+Properties+of+%5BM%28OCN%292%28urea%29%5D+and+M%28OCN%292+with+M%3DSr%2C+Eu&rft.volume=15&rft.issue=25&rft.pages=%3Cspan+class%3D%22nowrap%22%3E6186-%3C%2Fspan%3E6193&rft.date=2009&rft_id=info%3Adoi%2F10.1002%2Fchem.200900053&rft_id=info%3Apmid%2F19444832&rft.au=Sandro+Pagano&rft.au=Giuseppe+Montana&rft.au=Claudia+Wickleder&rft.au=Wolfgang+Schnick&rft_id=https%3A%2F%2Fdoi.org%2F10.1002%252Fchem.200900053&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanate" class="Z3988"></span></span> </li> <li id="cite_note-ChemicalElements-13"><span class="mw-cite-backlink">^ <a href="#cite_ref-ChemicalElements_13-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ChemicalElements_13-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGreenwoodEarnshaw1997" class="citation book cs1"><a href="/wiki/Norman_Greenwood" title="Norman Greenwood">Greenwood, Norman N.</a>; Earnshaw, Alan (1997). <i>Chemistry of the Elements</i> (2nd ed.). <a href="/wiki/Butterworth-Heinemann" title="Butterworth-Heinemann">Butterworth-Heinemann</a>. p. 325. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-037941-8" title="Special:BookSources/978-0-08-037941-8"><bdi>978-0-08-037941-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Chemistry+of+the+Elements&rft.pages=325&rft.edition=2nd&rft.pub=Butterworth-Heinemann&rft.date=1997&rft.isbn=978-0-08-037941-8&rft.aulast=Greenwood&rft.aufirst=Norman+N.&rft.au=Earnshaw%2C+Alan&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanate" class="Z3988"></span> (click <a rel="nofollow" class="external text" href="https://books.google.com/books?id=EvTI-ouH3SsC&q=cyanato">here</a>)</span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBrittonDunitz1965" class="citation journal cs1">Britton, D.; Dunitz, J. D. (1965). <a rel="nofollow" class="external text" href="https://scripts.iucr.org/cgi-bin/paper?a04540">"The crystal structure of silver cyanate"</a>. <i>Acta Crystallographica</i>. <b>18</b> (3): <span class="nowrap">424–</span>428. <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/10.1107%2FS0365110X65000944">10.1107/S0365110X65000944</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Crystallographica&rft.atitle=The+crystal+structure+of+silver+cyanate&rft.volume=18&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E424-%3C%2Fspan%3E428&rft.date=1965&rft_id=info%3Adoi%2F10.1107%2FS0365110X65000944&rft.aulast=Britton&rft.aufirst=D.&rft.au=Dunitz%2C+J.+D.&rft_id=https%3A%2F%2Fscripts.iucr.org%2Fcgi-bin%2Fpaper%3Fa04540&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanate" class="Z3988"></span></span> </li> <li id="cite_note-cno-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-cno_15-0">^</a></b></span> <span class="reference-text">Nakamoto, Part B, pp 121–123.</span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text">Greenwood, Table 8.9</span> </li> <li id="cite_note-Seymour-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-Seymour_17-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSeymourKauffman1992" class="citation journal cs1">Seymour, Raymond B.; <a href="/wiki/George_B._Kauffman" class="mw-redirect" title="George B. Kauffman">Kauffman, George B.</a> (1992). "Polyurethanes: A Class of Modern Versatile Materials". <i><a href="/wiki/J._Chem._Educ." class="mw-redirect" title="J. Chem. Educ.">J. Chem. Educ.</a></i> <b>69</b> (11): 909. <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/1992JChEd..69..909S">1992JChEd..69..909S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fed069p909">10.1021/ed069p909</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Chem.+Educ.&rft.atitle=Polyurethanes%3A+A+Class+of+Modern+Versatile+Materials&rft.volume=69&rft.issue=11&rft.pages=909&rft.date=1992&rft_id=info%3Adoi%2F10.1021%2Fed069p909&rft_id=info%3Abibcode%2F1992JChEd..69..909S&rft.aulast=Seymour&rft.aufirst=Raymond+B.&rft.au=Kauffman%2C+George+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanate" 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=Cyanate&action=edit&section=7" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://www.fishersci.com/store/msds?partNumber=AC201111000&countryCode=US&language=en">Material Safety Data Sheet for potassium cyanate</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Bibliography">Bibliography</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanate&action=edit&section=8" title="Edit section: Bibliography"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGreenwoodEarnshaw1997" class="citation book cs1"><a href="/wiki/Norman_Greenwood" title="Norman Greenwood">Greenwood, Norman N.</a>; Earnshaw, Alan (1997). <i>Chemistry of the Elements</i> (2nd ed.). <a href="/wiki/Butterworth-Heinemann" title="Butterworth-Heinemann">Butterworth-Heinemann</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-037941-8" title="Special:BookSources/978-0-08-037941-8"><bdi>978-0-08-037941-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Chemistry+of+the+Elements&rft.edition=2nd&rft.pub=Butterworth-Heinemann&rft.date=1997&rft.isbn=978-0-08-037941-8&rft.aulast=Greenwood&rft.aufirst=Norman+N.&rft.au=Earnshaw%2C+Alan&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanate" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNakamoto1997" class="citation book cs1">Nakamoto, K. (1997). <i>Infrared and Raman spectra of Inorganic and Coordination compounds</i>. Part A (5th ed.). Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-16394-5" title="Special:BookSources/0-471-16394-5"><bdi>0-471-16394-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Infrared+and+Raman+spectra+of+Inorganic+and+Coordination+compounds&rft.series=Part+A&rft.edition=5th&rft.pub=Wiley&rft.date=1997&rft.isbn=0-471-16394-5&rft.aulast=Nakamoto&rft.aufirst=K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanate" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNakamoto1997" class="citation book cs1">Nakamoto, K. (1997). <i>Infrared and Raman spectra of Inorganic and Coordination compounds</i>. Part B (5th ed.). Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-16392-9" title="Special:BookSources/0-471-16392-9"><bdi>0-471-16392-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Infrared+and+Raman+spectra+of+Inorganic+and+Coordination+compounds&rft.series=Part+B&rft.edition=5th&rft.pub=Wiley&rft.date=1997&rft.isbn=0-471-16392-9&rft.aulast=Nakamoto&rft.aufirst=K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanate" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWells1962" class="citation book cs1">Wells, A.F (1962). <i>Structural Inorganic Chemistry</i> (3rd. ed.). Oxford: Clarendon Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-19-855125-8" title="Special:BookSources/0-19-855125-8"><bdi>0-19-855125-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Structural+Inorganic+Chemistry&rft.place=Oxford&rft.edition=3rd.&rft.pub=Clarendon+Press&rft.date=1962&rft.isbn=0-19-855125-8&rft.aulast=Wells&rft.aufirst=A.F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanate" class="Z3988"></span></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline 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href="/wiki/Template:Cyanates" title="Template:Cyanates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cyanates" title="Template talk:Cyanates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cyanates" title="Special:EditPage/Template:Cyanates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Salts_and_covalent_derivatives_of_the_cyanate_ion134" style="font-size:114%;margin:0 4em">Salts and covalent derivatives of the <a class="mw-selflink selflink">cyanate</a> ion</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"><div class="mw-collapsible-content" style="overflow-x:auto"> <table class="center"> <tbody><tr style="background-color:mistyrose"> <td><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">HNCO</a> </td> <td style="background-color:white;color:inherit;border:none"> </td> <td style="background-color:white;color:inherit;border:none" colspan="11" rowspan="3"> </td> <td style="background-color:white;color:inherit;border:none" colspan="5"> </td> <td>He </td></tr> <tr style="background-color:mistyrose;color:black;"> <td><a href="/w/index.php?title=Lithium_cyanate&action=edit&redlink=1" class="new" title="Lithium cyanate (page does not exist)">LiOCN</a> </td> <td>Be </td> <td>B </td> <td>C </td> <td><a href="/wiki/Ammonium_cyanate" title="Ammonium cyanate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NH<sub class="template-chem2-sub">4</sub>OCN</span></a> </td> <td><a class="mw-selflink selflink"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">OCN<sup class="template-chem2-sup">−</sup></span></a><br /><a href="/wiki/Isocyanate" title="Isocyanate">-NCO</a><br /><a href="/w/index.php?title=Dicyanoether&action=edit&redlink=1" class="new" title="Dicyanoether (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O(CN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td>F </td> <td>Ne </td></tr> <tr style="background-color:mistyrose;color:black;"> <td><a href="/wiki/Sodium_cyanate" title="Sodium cyanate">NaOCN</a> </td> <td><a href="/w/index.php?title=Magnesium_cyanate&action=edit&redlink=1" class="new" title="Magnesium cyanate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Mg(OCN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td>Al </td> <td><a href="/w/index.php?title=Silicon_tetracyanate&action=edit&redlink=1" class="new" title="Silicon tetracyanate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Si(OCN)<sub class="template-chem2-sub">4</sub></span></a> </td> <td>P </td> <td>S </td> <td>Cl </td> <td>Ar </td></tr> <tr style="background-color:mistyrose;color:black;"> <td><a href="/wiki/Potassium_cyanate" title="Potassium cyanate">KOCN</a> </td> <td><a href="/w/index.php?title=Calcium_cyanate&action=edit&redlink=1" class="new" title="Calcium cyanate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ca(OCN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;color:inherit;border:none"> </td> <td>Sc </td> <td>Ti </td> <td>V </td> <td>Cr </td> <td>Mn </td> <td>Fe </td> <td><i><a href="/wiki/Cobalt(II)_cyanate" title="Cobalt(II) cyanate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Co(OCN)<sub class="template-chem2-sub">2</sub></span></a></i> </td> <td>Ni </td> <td><a href="/w/index.php?title=Copper(I)_cyanate&action=edit&redlink=1" class="new" title="Copper(I) cyanate (page does not exist)">CuOCN</a> </td> <td>Zn </td> <td>Ga </td> <td>Ge </td> <td>As </td> <td>Se </td> <td>Br </td> <td>Kr </td></tr> <tr style="background-color:mistyrose;color:black;"> <td><a href="/w/index.php?title=Rubidium_cyanate&action=edit&redlink=1" class="new" title="Rubidium cyanate (page does not exist)">RbOCN</a> </td> <td><a href="/w/index.php?title=Strontium_cyanate&action=edit&redlink=1" class="new" title="Strontium cyanate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sr(OCN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;color:inherit;border:none"> </td> <td>Y </td> <td>Zr </td> <td>Nb </td> <td>Mo </td> <td>Tc </td> <td>Ru </td> <td>Rh </td> <td>Pd </td> <td><a href="/wiki/Silver_cyanate" title="Silver cyanate">AgOCN</a> </td> <td>Cd </td> <td>In </td> <td>Sn </td> <td>Sb </td> <td>Te </td> <td>I </td> <td>Xe </td></tr> <tr style="background-color:mistyrose;color:black;"> <td><a href="/w/index.php?title=Cesium_cyanate&action=edit&redlink=1" class="new" title="Cesium cyanate (page does not exist)">CsOCN</a> </td> <td><a href="/w/index.php?title=Barium_cyanate&action=edit&redlink=1" class="new" title="Barium cyanate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ba(OCN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;color:inherit;border:none">* </td> <td>Lu </td> <td>Hf </td> <td>Ta </td> <td>W </td> <td>Re </td> <td>Os </td> <td>Ir </td> <td>Pt </td> <td>Au </td> <td>Hg </td> <td><a href="/w/index.php?title=Thallium(I)_cyanate&action=edit&redlink=1" class="new" title="Thallium(I) cyanate (page does not exist)">TlOCN</a> </td> <td><a href="/w/index.php?title=Lead_cyanate&action=edit&redlink=1" class="new" title="Lead cyanate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pb(OCN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td>Bi </td> <td>Po </td> <td>At </td> <td>Rn </td></tr> <tr style="background-color:mistyrose;color:black;"> <td>Fr </td> <td>Ra </td> <td style="background-color:white;color:inherit;border:none">** </td> <td>Lr </td> <td>Rf </td> <td>Db </td> <td>Sg </td> <td>Bh </td> <td>Hs </td> <td>Mt </td> <td>Ds </td> <td>Rg </td> <td>Cn </td> <td>Nh </td> <td>Fl </td> <td>Mc </td> <td>Lv </td> <td>Ts </td> <td>Og </td></tr> <tr> <td style="background-color:white;color:inherit;border:none" colspan="2" rowspan="3"> </td> <td style="background-color:white;color:inherit;border:none" colspan="20">  </td></tr> <tr style="background-color:mistyrose;color:black;"> <td style="background-color:white;color:inherit;border:none">* </td> <td>La </td> <td>Ce </td> <td>Pr </td> <td>Nd </td> <td>Pm </td> <td>Sm </td> <td><a href="/w/index.php?title=Europium(II)_cyanate&action=edit&redlink=1" class="new" title="Europium(II) cyanate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Eu(OCN)<sub class="template-chem2-sub">2</sub></span></a> </td> <td>Gd </td> <td>Tb </td> <td>Dy </td> <td>Ho </td> <td>Er </td> <td>Tm </td> <td>Yb </td></tr> <tr style="background-color:mistyrose;color:black;"> <td style="background-color:white;color:inherit;border:none">** </td> <td>Ac </td> <td>Th </td> <td>Pa </td> <td>U </td> <td>Np </td> <td>Pu </td> <td>Am </td> <td>Cm </td> <td>Bk </td> <td>Cf </td> <td>Es </td> <td>Fm </td> <td>Md </td> <td>No </td></tr></tbody></table></div> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Inorganic_compounds_of_carbon_and_related_ions134" 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_ions134" 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 href="/wiki/Carbon_suboxide" title="Carbon suboxide">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 class="mw-selflink selflink">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="Nitrogen_species87" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed 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:Nitrogen_compounds" title="Template:Nitrogen compounds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nitrogen_compounds" title="Template talk:Nitrogen compounds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nitrogen_compounds" title="Special:EditPage/Template:Nitrogen compounds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nitrogen_species87" style="font-size:114%;margin:0 4em"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> species</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Hydrides</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/Ammonia" title="Ammonia">NH<sub>3</sub></a></li> <li><a href="/wiki/Ammonium" title="Ammonium">NH<sub>4</sub><sup>+</sup></a></li> <li><a href="/wiki/Metal_amides#Alkali_metal_amides" title="Metal amides">NH<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Nitride" title="Nitride">N<sup>3−</sup></a></li> <li><a href="/wiki/Hydroxylamine" title="Hydroxylamine">NH<sub>2</sub>OH</a></li> <li><a href="/wiki/Hydrazine" title="Hydrazine">N<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Hydrazoic_acid" title="Hydrazoic acid">HN<sub>3</sub></a></li> <li><a href="/wiki/Azide" title="Azide">N<sub>3</sub><sup>−</sup></a></li> <li><a href="/wiki/Nitrogen_pentahydride" title="Nitrogen pentahydride"><i>NH<sub>5</sub></i></a> (?)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Organic</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/Amine" title="Amine">NR<sub>3</sub></a></li> <li><a href="/wiki/Imine" title="Imine">>C=NR</a></li> <li><a href="/wiki/Amide" title="Amide">−CONR<sub>2</sub></a></li> <li><a href="/wiki/Nitrile" title="Nitrile">−CN</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">HCN</a></li> <li><a href="/wiki/Cyanide" title="Cyanide">CN<sup>−</sup></a></li> <li><a href="/wiki/Cyanogen" title="Cyanogen">(CN)<sub>2</sub></a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">H<sub>2</sub>NCN</a></li> <li><a class="mw-selflink selflink">HOCN</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">HNCO</a></li> <li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">HNCS</a></li> <li><a href="/wiki/Diazomethane" title="Diazomethane">CH<sub>2</sub>N<sub>2</sub></a></li> <li><a href="/wiki/Nitroso" title="Nitroso">–NO</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">–NO<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen_oxide" title="Nitrogen oxide">Oxides</a></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/Nitric_oxide" title="Nitric oxide">NO</a> / <a href="/wiki/Dinitrogen_dioxide" title="Dinitrogen dioxide">(NO)<sub>2</sub></a></li> <li><a href="/wiki/Dinitrogen_trioxide" title="Dinitrogen trioxide">N<sub>2</sub>O<sub>3</sub></a></li> <li><a href="/wiki/Nitrous_acid" title="Nitrous acid">HNO<sub>2</sub></a> / <a href="/wiki/Nitrite" title="Nitrite">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a> / <a href="/wiki/Nitrosonium" title="Nitrosonium">NO<sup>+</sup></a></li> <li><a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">NO<sub>2</sub></a> / <a href="/wiki/Dinitrogen_tetroxide" title="Dinitrogen tetroxide">(NO<sub>2</sub>)<sub>2</sub></a></li> <li><a href="/wiki/Dinitrogen_pentoxide" title="Dinitrogen pentoxide">N<sub>2</sub>O<sub>5</sub></a></li> <li><a href="/wiki/Nitric_acid" title="Nitric acid">HNO<sub>3</sub></a> / <a href="/wiki/Nitrate" title="Nitrate">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></a> / <a href="/wiki/Nitronium" class="mw-redirect" title="Nitronium">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a></li> <li><a href="/wiki/Nitrate_radical" title="Nitrate radical">NO<sub>3</sub></a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">HNO</a> / <a href="/wiki/Hyponitrous_acid" title="Hyponitrous acid">(HON)<sub>2</sub></a> / <a href="/wiki/Hyponitrite" title="Hyponitrite">N<sub>2</sub>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a> / <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">N<sub>2</sub>O</a></li> <li><a href="/wiki/Nitramide" title="Nitramide">H<sub>2</sub>NNO<sub>2</sub></a></li> <li><a href="/wiki/Peroxynitrous_acid" title="Peroxynitrous acid">HO<sub>2</sub>NO</a> / <a href="/wiki/Peroxynitrite" title="Peroxynitrite">ONOO<sup>−</sup></a></li> <li><a href="/wiki/Peroxynitric_acid" title="Peroxynitric acid">HO<sub>2</sub>NO<sub>2</sub></a> / <a href="/wiki/Peroxynitrate" title="Peroxynitrate">O<sub>2</sub>NOO<sup>−</sup></a></li> <li><a href="/wiki/Orthonitrate" title="Orthonitrate">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">3−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span></a></li> <li><a href="/wiki/Nitroxylic_acid" title="Nitroxylic acid">H<sub>4</sub>N<sub>2</sub>O<sub>4</sub></a> / <a href="/wiki/Angeli%27s_salt" title="Angeli's salt">N<sub>2</sub>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Halides</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/Nitrogen_monofluoride" title="Nitrogen monofluoride">NF</a></li> <li><a href="/wiki/Nitrogen_difluoride" title="Nitrogen difluoride">NF<sub>2</sub></a></li> <li><a href="/wiki/Nitrogen_trifluoride" title="Nitrogen trifluoride">NF<sub>3</sub></a></li> <li><a href="/wiki/Nitrogen_pentafluoride" title="Nitrogen pentafluoride"><i>NF<sub>5</sub></i></a> (?)</li> <li><a href="/wiki/Nitrogen_trichloride" title="Nitrogen trichloride">NCl<sub>3</sub></a></li> <li><a href="/wiki/Nitrogen_tribromide" title="Nitrogen tribromide">NBr<sub>3</sub></a></li> <li><a href="/wiki/Nitrogen_triiodide" title="Nitrogen triiodide">NI<sub>3</sub></a></li> <li><a href="/wiki/Fluorine_azide" title="Fluorine azide">FN<sub>3</sub></a></li> <li><a href="/wiki/Chlorine_azide" title="Chlorine azide">ClN<sub>3</sub></a></li> <li><a href="/wiki/Bromine_azide" title="Bromine azide">BrN<sub>3</sub></a></li> <li><a href="/wiki/Iodine_azide" title="Iodine azide">IN<sub>3</sub></a></li> <li><a href="/wiki/Fluoroamine" title="Fluoroamine">NH<sub>2</sub>F</a></li> <li><a href="/wiki/Dinitrogen_difluoride" title="Dinitrogen difluoride">N<sub>2</sub>F<sub>2</sub></a></li> <li><a href="/wiki/Monochloramine" title="Monochloramine">NH<sub>2</sub>Cl</a></li> <li><a href="/w/index.php?title=Difluoramine&action=edit&redlink=1" class="new" title="Difluoramine (page does not exist)">NHF<sub>2</sub></a></li> <li><a href="/wiki/Dichloramine" title="Dichloramine">NHCl<sub>2</sub></a></li> <li><a href="/w/index.php?title=Dibromamine&action=edit&redlink=1" class="new" title="Dibromamine (page does not exist)">NHBr<sub>2</sub></a></li> <li><a href="/w/index.php?title=Diiodoamine&action=edit&redlink=1" class="new" title="Diiodoamine (page does not exist)">NHI<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxidation_state" title="Oxidation state">Oxidation states</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><span style="font-size:112%;"><b><a href="/wiki/Nitride" title="Nitride">−3</a></b></span>, <a href="/wiki/Hydrazine" title="Hydrazine">−2</a>, <a href="/wiki/Hydroxylamine" title="Hydroxylamine">−1</a>, 0, <a href="/wiki/Nitroxyl" title="Nitroxyl">+1</a>, <a href="/wiki/Nitric_oxide" title="Nitric oxide">+2</a>, <span style="font-size:112%;"><b><a href="/wiki/Nitrite" title="Nitrite">+3</a></b></span>, <a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">+4</a>, <span style="font-size:112%;"><b><a href="/wiki/Nitrate" title="Nitrate">+5</a></b></span> (a strongly <a href="/wiki/Acid" title="Acid">acidic</a> oxide)</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"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"></div><div role="navigation" class="navbox" aria-labelledby="Functional_groups729" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed 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:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups729" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silicon" title="Silicon">Silicon</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Silane" title="Silane">Silane</a> <ul><li><a href="/wiki/Hydrosilane" class="mw-redirect" title="Hydrosilane">Hydrosilane</a></li> <li><a href="/wiki/Chlorosilane" title="Chlorosilane">Chlorosilane</a></li></ul></li> <li><a href="/wiki/Organosilicon_chemistry#Silenes" title="Organosilicon chemistry">Silene</a></li> <li><a href="/wiki/Silanol" title="Silanol">Silanol</a></li> <li><a href="/wiki/Siloxide" title="Siloxide">Siloxide</a></li> <li><a href="/wiki/Siloxane" title="Siloxane">Siloxane</a></li> <li><a href="/wiki/Silanone" title="Silanone">Silanone</a></li> <li><a href="/wiki/Silyl_ether" title="Silyl ether">Silether</a></li> <li><a href="/wiki/Metalloles" class="mw-redirect" title="Metalloles">Silole</a></li> <li><a href="/wiki/Silatrane" class="mw-redirect" title="Silatrane">Silatrane</a></li> <li><a href="/wiki/Silicate" title="Silicate">Silicate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Thioether" class="mw-redirect" title="Thioether">Thioether</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li> <li><a href="/wiki/Selenide#Inorganic_selenides" title="Selenide">Selenoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li> <li><a href="/wiki/Telluride_(chemistry)#Organic_tellurides" title="Telluride (chemistry)">telluroether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polonium" title="Polonium">Polonium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Polonium_hydride#Properties" title="Polonium hydride">Polonol</a></li> <li><a href="/wiki/Organopolonium_chemistry" title="Organopolonium chemistry">Polonoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: 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