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id="toc-Classification-sublist" class="vector-toc-list"> <li id="toc-Inorganic_rings" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Inorganic_rings"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Inorganic rings</span> </div> </a> <ul id="toc-Inorganic_rings-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Notes_on_lists" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes_on_lists"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Notes on lists</span> </div> </a> <ul id="toc-Notes_on_lists-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-3-membered_rings" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#3-membered_rings"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>3-membered rings</span> </div> </a> <ul id="toc-3-membered_rings-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-4-membered_rings" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#4-membered_rings"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>4-membered rings</span> </div> </a> <ul id="toc-4-membered_rings-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-5-membered_rings" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#5-membered_rings"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>5-membered rings</span> </div> </a> <ul id="toc-5-membered_rings-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-6-membered_rings" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#6-membered_rings"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>6-membered rings</span> </div> </a> <ul id="toc-6-membered_rings-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-7-membered_rings" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#7-membered_rings"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>7-membered rings</span> </div> </a> <ul id="toc-7-membered_rings-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-8-membered_rings" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#8-membered_rings"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>8-membered rings</span> </div> </a> <ul id="toc-8-membered_rings-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-9-membered_rings" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#9-membered_rings"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>9-membered rings</span> </div> </a> <ul id="toc-9-membered_rings-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Images_of_rings_with_one_heteroatom" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Images_of_rings_with_one_heteroatom"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Images of rings with one heteroatom</span> </div> </a> <ul id="toc-Images_of_rings_with_one_heteroatom-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fused/condensed_rings" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Fused/condensed_rings"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Fused/condensed rings</span> </div> </a> <ul id="toc-Fused/condensed_rings-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History_of_heterocyclic_chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History_of_heterocyclic_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>History of heterocyclic chemistry</span> </div> </a> <ul id="toc-History_of_heterocyclic_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">13</span> <span>Uses</span> </div> </a> <ul id="toc-Uses-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">14</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">15</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">16</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Heterocyclic compound</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 54 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-54" 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">54 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/%D9%85%D8%B1%D9%83%D8%A8_%D8%AD%D9%84%D9%82%D9%8A_%D8%BA%D9%8A%D8%B1_%D9%85%D8%AA%D8%AC%D8%A7%D9%86%D8%B3" title="مركب حلقي غير متجانس – Arabic" lang="ar" hreflang="ar" data-title="مركب حلقي غير متجانس" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Heterotsiklik_birl%C9%99%C5%9Fm%C9%99l%C9%99r" title="Heterotsiklik birləşmələr – Azerbaijani" lang="az" hreflang="az" data-title="Heterotsiklik birləşmələr" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AC%E0%A6%BF%E0%A6%B7%E0%A6%AE%E0%A6%9A%E0%A6%BE%E0%A6%95%E0%A7%8D%E0%A6%B0%E0%A6%BF%E0%A6%95_%E0%A6%AF%E0%A7%8C%E0%A6%97" title="বিষমচাক্রিক যৌগ – Bangla" lang="bn" hreflang="bn" data-title="বিষমচাক্রিক যৌগ" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%93%D0%B5%D1%82%D1%8D%D1%80%D0%B0%D1%86%D1%8B%D0%BA%D0%BB%D1%96%D1%87%D0%BD%D1%8B%D1%8F_%D0%B7%D0%BB%D1%83%D1%87%D1%8D%D0%BD%D0%BD%D1%96" title="Гетэрацыклічныя злучэнні – Belarusian" lang="be" hreflang="be" data-title="Гетэрацыклічныя злучэнні" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A5%D0%B5%D1%82%D0%B5%D1%80%D0%BE%D1%86%D0%B8%D0%BA%D0%BB%D0%B8%D1%87%D0%BD%D0%BE_%D1%81%D1%8A%D0%B5%D0%B4%D0%B8%D0%BD%D0%B5%D0%BD%D0%B8%D0%B5" title="Хетероциклично съединение – Bulgarian" lang="bg" hreflang="bg" data-title="Хетероциклично съединение" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Heterocikli%C4%8Dni_spoj" title="Heterociklični spoj – Bosnian" lang="bs" hreflang="bs" data-title="Heterociklični spoj" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Compost_heteroc%C3%ADclic" title="Compost heterocíclic – Catalan" lang="ca" hreflang="ca" data-title="Compost heterocíclic" 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/Heterocyklick%C3%A9_slou%C4%8Deniny" title="Heterocyklické sloučeniny – Czech" lang="cs" hreflang="cs" data-title="Heterocyklické sloučeniny" 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/Heterocyklisk_forbindelse" title="Heterocyklisk forbindelse – Danish" lang="da" hreflang="da" data-title="Heterocyklisk forbindelse" 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-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://de.wikipedia.org/wiki/Heterocyclen" title="Heterocyclen – German" lang="de" hreflang="de" data-title="Heterocyclen" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Heterots%C3%BCklilised_%C3%BChendid" title="Heterotsüklilised ühendid – Estonian" lang="et" hreflang="et" data-title="Heterotsüklilised ühendid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%95%CF%84%CE%B5%CF%81%CE%BF%CE%BA%CF%85%CE%BA%CE%BB%CE%B9%CE%BA%CE%AD%CF%82_%CE%B5%CE%BD%CF%8E%CF%83%CE%B5%CE%B9%CF%82" title="Ετεροκυκλικές ενώσεις – Greek" lang="el" hreflang="el" data-title="Ετεροκυκλικές ενώσεις" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Compuesto_heteroc%C3%ADclico" title="Compuesto heterocíclico – Spanish" lang="es" hreflang="es" data-title="Compuesto heterocíclico" 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/Heterocikla_kombina%C4%B5o" title="Heterocikla kombinaĵo – Esperanto" lang="eo" hreflang="eo" data-title="Heterocikla kombinaĵo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Konposatu_heterozikliko" title="Konposatu heterozikliko – Basque" lang="eu" hreflang="eu" data-title="Konposatu heterozikliko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%D8%B1%DA%A9%DB%8C%D8%A8_%D9%86%D8%A7%D8%AC%D9%88%D8%B1%D8%AD%D9%84%D9%82%D9%87" title="ترکیب ناجورحلقه – Persian" lang="fa" hreflang="fa" data-title="ترکیب ناجورحلقه" 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/H%C3%A9t%C3%A9rocycle" title="Hétérocycle – French" lang="fr" hreflang="fr" data-title="Hétérocycle" 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/Comhdh%C3%BAil_heitreafh%C3%A1inneach" title="Comhdhúil heitreafháinneach – Irish" lang="ga" hreflang="ga" data-title="Comhdhúil heitreafháinneach" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Composto_heteroc%C3%ADclico" title="Composto heterocíclico – Galician" lang="gl" hreflang="gl" data-title="Composto heterocíclico" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%97%A4%ED%85%8C%EB%A1%9C%EA%B3%A0%EB%A6%AC_%ED%99%94%ED%95%A9%EB%AC%BC" title="헤테로고리 화합물 – Korean" lang="ko" hreflang="ko" data-title="헤테로고리 화합물" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%80%D5%A5%D5%BF%D5%A5%D6%80%D5%B8%D6%81%D5%AB%D5%AF%D5%AC%D5%AB%D5%AF_%D5%B4%D5%AB%D5%A1%D6%81%D5%B8%D6%82%D5%A9%D5%B5%D5%B8%D6%82%D5%B6%D5%B6%D5%A5%D6%80" title="Հետերոցիկլիկ միացություններ – Armenian" lang="hy" hreflang="hy" data-title="Հետերոցիկլիկ միացություններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Heterocikli%C4%8Dki_aromatski_spojevi" title="Heterociklički aromatski spojevi – Croatian" lang="hr" hreflang="hr" data-title="Heterociklički aromatski spojevi" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Senyawa_heterosiklik" title="Senyawa heterosiklik – Indonesian" lang="id" hreflang="id" data-title="Senyawa heterosiklik" 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/Composto_eterociclico" title="Composto eterociclico – Italian" lang="it" hreflang="it" data-title="Composto eterociclico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%AA%D7%A8%D7%9B%D7%95%D7%91%D7%AA_%D7%94%D7%98%D7%A8%D7%95%D7%A6%D7%99%D7%A7%D7%9C%D7%99%D7%AA" title="תרכובת הטרוציקלית – Hebrew" lang="he" hreflang="he" data-title="תרכובת הטרוציקלית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Senyawa_heterosiklik" title="Senyawa heterosiklik – Javanese" lang="jv" hreflang="jv" data-title="Senyawa heterosiklik" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%B0%E1%83%94%E1%83%A2%E1%83%94%E1%83%A0%E1%83%9D%E1%83%AA%E1%83%98%E1%83%99%E1%83%9A%E1%83%A3%E1%83%A0%E1%83%98_%E1%83%9C%E1%83%90%E1%83%94%E1%83%A0%E1%83%97%E1%83%94%E1%83%91%E1%83%98" title="ჰეტეროციკლური ნაერთები – Georgian" lang="ka" hreflang="ka" data-title="ჰეტეროციკლური ნაერთები" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%93%D0%B5%D1%82%D0%B5%D1%80%D0%BE%D1%86%D0%B8%D0%BA%D0%BB%D0%B4%D1%96_%D2%9B%D0%BE%D1%81%D1%8B%D0%BB%D1%8B%D1%81%D1%82%D0%B0%D1%80" title="Гетероциклді қосылыстар – Kazakh" lang="kk" hreflang="kk" data-title="Гетероциклді қосылыстар" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%93%D0%B5%D1%82%D0%B5%D1%80%D0%BE%D1%86%D0%B8%D0%BA%D0%BB%D0%B4%D2%AF%D2%AF_%D0%B1%D0%B8%D1%80%D0%B8%D0%BA%D0%BC%D0%B5%D0%BB%D0%B5%D1%80" title="Гетероциклдүү бирикмелер – Kyrgyz" lang="ky" hreflang="ky" data-title="Гетероциклдүү бирикмелер" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Heterocikliskie_savienojumi" title="Heterocikliskie savienojumi – Latvian" lang="lv" hreflang="lv" data-title="Heterocikliskie savienojumi" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Cumpost_eteruciclich" title="Cumpost eteruciclich – Lombard" lang="lmo" hreflang="lmo" data-title="Cumpost eteruciclich" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Heterociklusos_vegy%C3%BClet" title="Heterociklusos vegyület – Hungarian" lang="hu" hreflang="hu" data-title="Heterociklusos vegyület" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A5%D0%B5%D1%82%D0%B5%D1%80%D0%BE%D1%86%D0%B8%D0%BA%D0%BB%D0%B8%D1%87%D0%BD%D0%BE_%D1%81%D0%BE%D0%B5%D0%B4%D0%B8%D0%BD%D0%B5%D0%BD%D0%B8%D0%B5" title="Хетероциклично соединение – Macedonian" lang="mk" hreflang="mk" data-title="Хетероциклично соединение" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B9%E0%B5%86%E0%B4%9F%E0%B5%8D%E0%B4%B0%E0%B5%8B%E0%B4%B8%E0%B5%88%E0%B4%95%E0%B5%8D%E0%B4%B2%E0%B4%BF%E0%B4%95%E0%B5%8D_%E0%B4%B0%E0%B4%BE%E0%B4%B8%E0%B4%B8%E0%B4%82%E0%B4%AF%E0%B5%81%E0%B4%95%E0%B5%8D%E0%B4%A4%E0%B4%99%E0%B5%8D%E0%B4%99%E0%B5%BE" title="ഹെട്രോസൈക്ലിക് രാസസംയുക്തങ്ങൾ – Malayalam" lang="ml" hreflang="ml" data-title="ഹെട്രോസൈക്ലിക് രാസസംയുക്തങ്ങൾ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://nl.wikipedia.org/wiki/Heterocyclische_verbinding" title="Heterocyclische verbinding – Dutch" lang="nl" hreflang="nl" data-title="Heterocyclische verbinding" 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/%E8%A4%87%E7%B4%A0%E7%92%B0%E5%BC%8F%E5%8C%96%E5%90%88%E7%89%A9" title="複素環式化合物 – Japanese" lang="ja" hreflang="ja" data-title="複素環式化合物" 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/Heterosyklisk_forbindelse" title="Heterosyklisk forbindelse – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Heterosyklisk forbindelse" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Geterotsiklik_birikmalar" title="Geterotsiklik birikmalar – Uzbek" lang="uz" hreflang="uz" data-title="Geterotsiklik birikmalar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Zwi%C4%85zki_heterocykliczne" title="Związki heterocykliczne – Polish" lang="pl" hreflang="pl" data-title="Związki heterocykliczne" 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/Composto_heteroc%C3%ADclico" title="Composto heterocíclico – Portuguese" lang="pt" hreflang="pt" data-title="Composto heterocíclico" 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/Compus_heterociclic" title="Compus heterociclic – Romanian" lang="ro" hreflang="ro" data-title="Compus heterociclic" 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%93%D0%B5%D1%82%D0%B5%D1%80%D0%BE%D1%86%D0%B8%D0%BA%D0%BB%D0%B8%D1%87%D0%B5%D1%81%D0%BA%D0%B8%D0%B5_%D1%81%D0%BE%D0%B5%D0%B4%D0%B8%D0%BD%D0%B5%D0%BD%D0%B8%D1%8F" title="Гетероциклические соединения – Russian" lang="ru" hreflang="ru" data-title="Гетероциклические соединения" 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/Heterocyklick%C3%A1_zl%C3%BA%C4%8Denina" title="Heterocyklická zlúčenina – Slovak" lang="sk" hreflang="sk" data-title="Heterocyklická zlúčenina" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Heterocikli%C4%8Dna_spojina" title="Heterociklična spojina – Slovenian" lang="sl" hreflang="sl" data-title="Heterociklična spojina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Heterocikli%C4%8Dno_jedinjenje" title="Heterociklično jedinjenje – Serbian" lang="sr" hreflang="sr" data-title="Heterociklično jedinjenje" 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/Heterocikli%C4%8Dno_jedinjenje" title="Heterociklično jedinjenje – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Heterociklično jedinjenje" 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/Heterosyklinen_yhdiste" title="Heterosyklinen yhdiste – Finnish" lang="fi" hreflang="fi" data-title="Heterosyklinen yhdiste" 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/Heterocyklisk_f%C3%B6rening" title="Heterocyklisk förening – Swedish" lang="sv" hreflang="sv" data-title="Heterocyklisk förening" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Heterosiklik_bile%C5%9Fik" title="Heterosiklik bileşik – Turkish" lang="tr" hreflang="tr" data-title="Heterosiklik bileşik" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D0%B5%D1%82%D0%B5%D1%80%D0%BE%D1%86%D0%B8%D0%BA%D0%BB%D1%96%D1%87%D0%BD%D1%96_%D1%81%D0%BF%D0%BE%D0%BB%D1%83%D0%BA%D0%B8" title="Гетероциклічні сполуки – Ukrainian" lang="uk" hreflang="uk" data-title="Гетероциклічні сполуки" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a 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noexcerpt noprint searchaux" style="display:none">Molecule with one or more rings composed of different elements</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">For other uses of "ring structure", see <a href="/wiki/Ring_structure_(disambiguation)" class="mw-redirect mw-disambig" title="Ring structure (disambiguation)">Ring structure</a>.</div> <p class="mw-empty-elt"> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Heterocycle_compounds.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Heterocycle_compounds.jpg/280px-Heterocycle_compounds.jpg" decoding="async" width="280" height="525" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Heterocycle_compounds.jpg/420px-Heterocycle_compounds.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Heterocycle_compounds.jpg/560px-Heterocycle_compounds.jpg 2x" data-file-width="3222" data-file-height="6044" /></a><figcaption>Structures and names of common heterocyclic compounds</figcaption></figure> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Pyridine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Pyridine.svg/125px-Pyridine.svg.png" decoding="async" width="125" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Pyridine.svg/188px-Pyridine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/Pyridine.svg/250px-Pyridine.svg.png 2x" data-file-width="440" data-file-height="556" /></a><figcaption><a href="/wiki/Pyridine" title="Pyridine">Pyridine</a>, a heterocyclic compound</figcaption></figure> <p>A <b>heterocyclic compound</b> or <b>ring structure</b> is a <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic compound</a> that has atoms of at least two different <a href="/wiki/Chemical_element" title="Chemical element">elements</a> as members of its ring(s).<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> <b>Heterocyclic organic chemistry</b> is the branch of <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a> dealing with the synthesis, properties, and applications of <b>organic heterocycles</b>.<sup id="cite_ref-Gilchrist_2-0" class="reference"><a href="#cite_note-Gilchrist-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Examples of heterocyclic compounds include all of the <a href="/wiki/Nucleic_acids" class="mw-redirect" title="Nucleic acids">nucleic acids</a>, the majority of drugs, most <a href="/wiki/Biomass" title="Biomass">biomass</a> (<a href="/wiki/Cellulose" title="Cellulose">cellulose</a> and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles.<sup id="cite_ref-Rees_3-0" class="reference"><a href="#cite_note-Rees-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> 59% of US <a href="/wiki/FDA" class="mw-redirect" title="FDA">FDA</a>-approved drugs contain <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> heterocycles.<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> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Classification">Classification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=1" title="Edit section: Classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The study of organic heterocyclic chemistry focuses especially on organic unsaturated derivatives, and the preponderance of work and applications involves unstrained organic 5- and 6-membered rings. Included are <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>, <a href="/wiki/Thiophene" title="Thiophene">thiophene</a>, <a href="/wiki/Pyrrole" title="Pyrrole">pyrrole</a>, and <a href="/wiki/Furan" title="Furan">furan</a>. Another large class of organic heterocycles refers to those fused to <a href="/wiki/Benzene_ring" class="mw-redirect" title="Benzene ring">benzene rings</a>. For example, the fused benzene derivatives of pyridine, thiophene, pyrrole, and furan are <a href="/wiki/Quinoline" title="Quinoline">quinoline</a>, <a href="/wiki/Benzothiophene" title="Benzothiophene">benzothiophene</a>, <a href="/wiki/Indole" title="Indole">indole</a>, and <a href="/wiki/Benzofuran" title="Benzofuran">benzofuran</a>, respectively. The fusion of two benzene rings gives rise to a third large family of organic compounds. Analogs of the previously mentioned heterocycles for this third family of compounds are <a href="/wiki/Acridine" title="Acridine">acridine</a>, <a href="/wiki/Dibenzothiophene" title="Dibenzothiophene">dibenzothiophene</a>, <a href="/wiki/Carbazole" title="Carbazole">carbazole</a>, and <a href="/wiki/Dibenzofuran" title="Dibenzofuran">dibenzofuran</a>, respectively. </p><p>Heterocyclic organic compounds can be usefully classified based on their electronic structure. The saturated organic heterocycles behave like the acyclic derivatives. Thus, <a href="/wiki/Piperidine" title="Piperidine">piperidine</a> and <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a> are conventional <a href="/wiki/Amines" class="mw-redirect" title="Amines">amines</a> and <a href="/wiki/Ethers" class="mw-redirect" title="Ethers">ethers</a>, with modified steric profiles. Therefore, the study of organic heterocyclic chemistry focuses on organic unsaturated rings. </p> <div class="mw-heading mw-heading3"><h3 id="Inorganic_rings">Inorganic rings</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=2" title="Edit section: Inorganic rings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some heterocycles contain no carbon. Examples are <a href="/wiki/Borazine" title="Borazine">borazine</a> (B<sub>3</sub>N<sub>3</sub> ring), <a href="/wiki/Hexachlorophosphazene" title="Hexachlorophosphazene">hexachlorophosphazenes</a> (P<sub>3</sub>N<sub>3</sub> rings), and <a href="/wiki/Tetrasulfur_tetranitride" title="Tetrasulfur tetranitride">tetrasulfur tetranitride</a> S<sub>4</sub>N<sub>4</sub>. In comparison with organic heterocycles, which have numerous commercial applications, inorganic ring systems are mainly of theoretical interest. <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a> recommends the <a href="/wiki/Hantzsch-Widman_nomenclature" class="mw-redirect" title="Hantzsch-Widman nomenclature">Hantzsch-Widman nomenclature</a> for naming heterocyclic compounds.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Notes_on_lists">Notes on lists</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=3" title="Edit section: Notes on lists"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>"Heteroatoms" are atoms in the ring other than <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms.</li> <li>Names in italics are retained by <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> and do not follow the <a href="/wiki/Hantzsch-Widman_nomenclature" class="mw-redirect" title="Hantzsch-Widman nomenclature">Hantzsch-Widman nomenclature</a></li> <li>Some of the names refer to classes of compounds rather than individual compounds.</li> <li>Also no attempt is made to list <a href="/wiki/Isomers" class="mw-redirect" title="Isomers">isomers</a>.</li></ul> <div class="mw-heading mw-heading2"><h2 id="3-membered_rings">3-membered rings</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=4" title="Edit section: 3-membered rings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although subject to <a href="/wiki/Ring_strain" title="Ring strain">ring strain</a>, 3-membered heterocyclic rings are well characterized.<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> </p> <table class="wikitable"> <tbody><tr> <th colspan="3">Three-membered rings with one heteroatom </th></tr> <tr> <th>Heteroatom </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>Boron </td> <td><a href="/wiki/Borirane" title="Borirane">Borirane</a> </td> <td><a href="/wiki/Borirene" class="mw-redirect" title="Borirene">Borirene</a> </td></tr> <tr> <td>Nitrogen </td> <td><a href="/wiki/Aziridine" title="Aziridine">Aziridine</a> </td> <td><a href="/wiki/Azirine" title="Azirine">Azirine</a> </td></tr> <tr> <td>Oxygen </td> <td><a href="/wiki/Oxirane" class="mw-redirect" title="Oxirane">Oxirane</a><br />(<a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a>, <a href="/wiki/Epoxide" title="Epoxide">epoxides</a>) </td> <td><a href="/wiki/Oxirene" title="Oxirene">Oxirene</a> </td></tr> <tr> <td>Phosphorus </td> <td><a href="/wiki/Phosphirane" title="Phosphirane">Phosphirane</a> </td> <td><a href="/wiki/Phosphirene" title="Phosphirene">Phosphirene</a> </td></tr> <tr> <td>Sulfur </td> <td><a href="/wiki/Thiirane" title="Thiirane">Thiirane</a><br />(<a href="/wiki/Ethylene_sulfide" class="mw-redirect" title="Ethylene sulfide">ethylene sulfide</a>, <a href="/wiki/Episulfide" title="Episulfide">episulfides</a>) </td> <td><a href="/wiki/Thiirene" title="Thiirene">Thiirene</a> </td></tr> <tr> <th colspan="3">Three-membered rings with two heteroatoms </th></tr> <tr> <th>Heteroatoms </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>2 × Nitrogen </td> <td><a href="/wiki/Diaziridine" title="Diaziridine">Diaziridine</a> </td> <td><a href="/wiki/Diazirine" title="Diazirine">Diazirine</a> </td></tr> <tr> <td>Nitrogen + Oxygen </td> <td><a href="/wiki/Oxaziridine" title="Oxaziridine">Oxaziridine</a> </td> <td><a href="/w/index.php?title=Oxazirine&action=edit&redlink=1" class="new" title="Oxazirine (page does not exist)">Oxazirine</a> </td></tr> <tr> <td>Nitrogen + Sulfur </td> <td><a href="/w/index.php?title=Thiaziridine&action=edit&redlink=1" class="new" title="Thiaziridine (page does not exist)">Thiaziridine</a> </td> <td><a href="/w/index.php?title=Thiazirine&action=edit&redlink=1" class="new" title="Thiazirine (page does not exist)">Thiazirine</a> </td></tr> <tr> <td>2 × Oxygen </td> <td><a href="/wiki/Dioxirane" title="Dioxirane">Dioxirane</a> (highly unstable) </td> <td> </td></tr> <tr> <td>2 × Sulfur </td> <td><a href="/wiki/Dithiirane" class="mw-redirect" title="Dithiirane">Dithiirane</a> (highly unstable) </td> <td> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="4-membered_rings">4-membered rings</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=5" title="Edit section: 4-membered rings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <tbody><tr> <th colspan="3">Four-membered rings with one heteroatom </th></tr> <tr> <th>Heteroatom </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>Boron </td> <td><a href="/w/index.php?title=Boretane&action=edit&redlink=1" class="new" title="Boretane (page does not exist)">Boretane</a> </td> <td><a href="/w/index.php?title=Borete&action=edit&redlink=1" class="new" title="Borete (page does not exist)">Borete</a> </td></tr> <tr> <td>Nitrogen </td> <td><a href="/wiki/Azetidine" title="Azetidine">Azetidine</a> </td> <td><a href="/wiki/Azete" title="Azete">Azete</a> </td></tr> <tr> <td>Oxygen </td> <td><a href="/wiki/Oxetane" title="Oxetane">Oxetane</a> </td> <td><a href="/wiki/Oxete" class="mw-redirect" title="Oxete">Oxete</a> </td></tr> <tr> <td>Phosphorus </td> <td><a href="/wiki/Phosphetane" title="Phosphetane">Phosphetane</a> </td> <td><a href="/w/index.php?title=Phosphete&action=edit&redlink=1" class="new" title="Phosphete (page does not exist)">Phosphete</a> </td></tr> <tr> <td>Sulfur </td> <td><a href="/wiki/Thietane" title="Thietane">Thietane</a> </td> <td><a href="/wiki/Thiete" title="Thiete">Thiete</a> </td></tr> <tr> <th colspan="3">Four-membered rings with two heteroatoms </th></tr> <tr> <th>Heteroatoms </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>2 × Nitrogen </td> <td><a href="/w/index.php?title=Diazetidine&action=edit&redlink=1" class="new" title="Diazetidine (page does not exist)">Diazetidine</a> </td> <td><a href="/w/index.php?title=Diazete&action=edit&redlink=1" class="new" title="Diazete (page does not exist)">Diazete</a> </td></tr> <tr> <td>2 × Oxygen </td> <td><a href="/wiki/Dioxetane" title="Dioxetane">Dioxetane</a> </td> <td><a href="/w/index.php?title=Dioxete&action=edit&redlink=1" class="new" title="Dioxete (page does not exist)">Dioxete</a> </td></tr> <tr> <td>2 × Sulfur </td> <td><a href="/wiki/Dithietane" title="Dithietane">Dithietane</a> </td> <td><a href="/wiki/Dithiete" title="Dithiete">Dithiete</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="5-membered_rings">5-membered rings</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=6" title="Edit section: 5-membered rings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The 5-membered ring compounds containing <i>two</i> heteroatoms, at least one of which is nitrogen, are collectively called the <a href="/wiki/Azole" title="Azole">azoles</a>. <a href="/wiki/Thiazole" title="Thiazole">Thiazoles</a> and <a href="/wiki/Isothiazole" title="Isothiazole">isothiazoles</a> contain a sulfur and a nitrogen atom in the ring. <a href="/wiki/Dithiole" title="Dithiole">Dithioles</a> have two sulfur atoms. </p><p>A large group of 5-membered ring compounds with <i>three</i> or more heteroatoms also exists. One example is the class of <a href="/wiki/Dithiazole" title="Dithiazole">dithiazoles</a>, which contain two sulfur atoms and one nitrogen atom. </p> <table class="wikitable"> <tbody><tr> <th colspan="3">Five-membered rings with one heteroatom </th></tr> <tr> <th>Heteroatom </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td><a href="/wiki/Antimony" title="Antimony">Antimony</a> </td> <td><a href="/w/index.php?title=Stibolane&action=edit&redlink=1" class="new" title="Stibolane (page does not exist)">Stibolane</a> </td> <td><a href="/wiki/Stibole" title="Stibole">Stibole</a> </td></tr> <tr> <td><a href="/wiki/Arsenic" title="Arsenic">Arsenic</a> </td> <td><a href="/w/index.php?title=Arsolane&action=edit&redlink=1" class="new" title="Arsolane (page does not exist)">Arsolane</a> </td> <td><a href="/wiki/Arsole" title="Arsole">Arsole</a> </td></tr> <tr> <td><a href="/wiki/Bismuth" title="Bismuth">Bismuth</a> </td> <td><a href="/w/index.php?title=Bismolane&action=edit&redlink=1" class="new" title="Bismolane (page does not exist)">Bismolane</a> </td> <td><a href="/wiki/Bismole" title="Bismole">Bismole</a> </td></tr> <tr> <td><a href="/wiki/Boron" title="Boron">Boron</a> </td> <td><a href="/w/index.php?title=Borolane&action=edit&redlink=1" class="new" title="Borolane (page does not exist)">Borolane</a> </td> <td><a href="/wiki/Borole" title="Borole">Borole</a> </td></tr> <tr> <td><a href="/wiki/Germanium" title="Germanium">Germanium</a> </td> <td><a href="/w/index.php?title=Germolane&action=edit&redlink=1" class="new" title="Germolane (page does not exist)">Germolane</a> </td> <td><a href="/w/index.php?title=Germole&action=edit&redlink=1" class="new" title="Germole (page does not exist)">Germole</a> </td></tr> <tr> <td><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> </td> <td><i><a href="/wiki/Pyrrolidine" title="Pyrrolidine">Pyrrolidine</a></i><br />(<a href="/wiki/Azolidine" class="mw-redirect" title="Azolidine">Azolidine</a> not used) </td> <td><i><a href="/wiki/Pyrrole" title="Pyrrole">Pyrrole</a></i><br />(<a href="/wiki/Azole" title="Azole">Azole</a> not used)<br /><i><a href="/wiki/Pyrroline" title="Pyrroline">Pyrroline</a></i> (partially unsaturated) </td></tr> <tr> <td><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> </td> <td><a href="/wiki/Oxolane" class="mw-redirect" title="Oxolane">Oxolane</a> </td> <td><i><a href="/wiki/Furan" title="Furan">Furan</a></i><br />(<a href="/wiki/Oxole" class="mw-redirect" title="Oxole">Oxole</a> not used) </td></tr> <tr> <td><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a> </td> <td><a href="/wiki/Phospholane" title="Phospholane">Phospholane</a> </td> <td><a href="/wiki/Phosphole" title="Phosphole">Phosphole</a> </td></tr> <tr> <td><a href="/wiki/Selenium" title="Selenium">Selenium</a> </td> <td><a href="/w/index.php?title=Selenolane&action=edit&redlink=1" class="new" title="Selenolane (page does not exist)">Selenolane</a> </td> <td><a href="/wiki/Selenophene" title="Selenophene">Selenophene</a> </td></tr> <tr> <td><a href="/wiki/Silicon" title="Silicon">Silicon</a> </td> <td><a href="/w/index.php?title=Silolane&action=edit&redlink=1" class="new" title="Silolane (page does not exist)">Silolane</a> </td> <td><a href="/wiki/Silole" class="mw-redirect" title="Silole">Silole</a> </td></tr> <tr> <td><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a> </td> <td><a href="/wiki/Thiolane" class="mw-redirect" title="Thiolane">Thiolane</a> </td> <td><i><a href="/wiki/Thiophene" title="Thiophene">Thiophene</a></i><br />(<a href="/wiki/Thiole" class="mw-redirect" title="Thiole">Thiole</a> not used) </td></tr> <tr> <td><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a> </td> <td><a href="/w/index.php?title=Tellurolane&action=edit&redlink=1" class="new" title="Tellurolane (page does not exist)">Tellurolane</a> </td> <td><a href="/wiki/Tellurophene" class="mw-redirect" title="Tellurophene">Tellurophene</a> </td></tr> <tr> <td><a href="/wiki/Tin" title="Tin">Tin</a> </td> <td><a href="/w/index.php?title=Stannolane&action=edit&redlink=1" class="new" title="Stannolane (page does not exist)">Stannolane</a> </td> <td><a href="/wiki/Stannole" title="Stannole">Stannole</a> </td></tr> <tr> <th colspan="3">Five-membered rings with two heteroatoms </th></tr> <tr> <th>Heteroatoms </th> <th>Saturated </th> <th>Unsaturated (and partially unsaturated) </th></tr> <tr> <td>2 × Nitrogen </td> <td><i><a href="/wiki/Pyrazolidine" title="Pyrazolidine">Pyrazolidine</a></i> <br /><i><a href="/wiki/Imidazolidine" title="Imidazolidine">Imidazolidine</a></i> </td> <td><i><a href="/wiki/Pyrazole" title="Pyrazole">Pyrazole</a></i> (<i><a href="/wiki/Pyrazoline" title="Pyrazoline">Pyrazoline</a></i>)<br /><i><a href="/wiki/Imidazole" title="Imidazole">Imidazole</a></i> (<i><a href="/wiki/Imidazoline" title="Imidazoline">Imidazoline</a></i>) </td></tr> <tr> <td>Nitrogen + Oxygen </td> <td><a href="/wiki/Oxazolidine" title="Oxazolidine">Oxazolidine</a><br /><a href="/wiki/Isoxazolidine" title="Isoxazolidine">Isoxazolidine</a> </td> <td><a href="/wiki/Oxazole" title="Oxazole">Oxazole</a> (<a href="/wiki/Oxazoline" title="Oxazoline">Oxazoline</a>)<br /><a href="/wiki/Isoxazole" title="Isoxazole">Isoxazole</a> (<a href="/wiki/Isoxazoline" title="Isoxazoline">Isoxazoline</a>) </td></tr> <tr> <td>Nitrogen + Sulfur </td> <td><a href="/wiki/Thiazolidine" title="Thiazolidine">Thiazolidine</a><br /><a href="/w/index.php?title=Isothiazolidine&action=edit&redlink=1" class="new" title="Isothiazolidine (page does not exist)">Isothiazolidine</a> </td> <td><a href="/wiki/Thiazole" title="Thiazole">Thiazole</a> (<a href="/wiki/Thiazoline" title="Thiazoline">Thiazoline</a>)<br /><a href="/wiki/Isothiazole" title="Isothiazole">Isothiazole</a> (<a href="/w/index.php?title=Isothiazoline&action=edit&redlink=1" class="new" title="Isothiazoline (page does not exist)">Isothiazoline</a>) </td></tr> <tr> <td>Oxygen + Sulfur </td> <td><a href="/wiki/Oxathiolane" class="mw-redirect" title="Oxathiolane">Oxathiolane</a><br /><a href="/w/index.php?title=Isoxathiolane&action=edit&redlink=1" class="new" title="Isoxathiolane (page does not exist)">Isoxathiolane</a> </td> <td><a href="/w/index.php?title=Oxathiole&action=edit&redlink=1" class="new" title="Oxathiole (page does not exist)">Oxathiole</a><br /><a href="/w/index.php?title=Isoxathiole&action=edit&redlink=1" class="new" title="Isoxathiole (page does not exist)">Isoxathiole</a> </td></tr> <tr> <td>2 × Oxygen </td> <td><a href="/wiki/Dioxolane" title="Dioxolane">Dioxolane</a> </td> <td><a href="/w/index.php?title=Dioxole&action=edit&redlink=1" class="new" title="Dioxole (page does not exist)">Dioxole</a> </td></tr> <tr> <td>2 × Sulfur </td> <td><a href="/wiki/Dithiolane" title="Dithiolane">Dithiolane</a> </td> <td><a href="/wiki/Dithiole" title="Dithiole">Dithiole</a> </td></tr> <tr> <th colspan="3">Five-membered rings with three heteroatoms </th></tr> <tr> <th>Heteroatoms </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>3 × Nitrogen </td> <td> </td> <td><a href="/wiki/Triazole" title="Triazole">Triazole</a> </td></tr> <tr> <td>2 Nitrogen + Oxygen </td> <td> </td> <td><a href="/wiki/Oxadiazole" title="Oxadiazole">Oxadiazole</a> </td></tr> <tr> <td>2 Nitrogen + Sulfur </td> <td> </td> <td><a href="/wiki/Thiadiazole" class="mw-redirect" title="Thiadiazole">Thiadiazole</a> </td></tr> <tr> <td>Nitrogen + 2 Oxygen </td> <td> </td> <td><a href="/w/index.php?title=Dioxazole&action=edit&redlink=1" class="new" title="Dioxazole (page does not exist)">Dioxazole</a> </td></tr> <tr> <td>Nitrogen + 2 Sulfur </td> <td> </td> <td><a href="/wiki/Dithiazole" title="Dithiazole">Dithiazole</a> </td></tr> <tr> <th colspan="3">Five-membered rings with four heteroatoms </th></tr> <tr> <th>Heteroatoms </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>4 × Nitrogen </td> <td> </td> <td><a href="/wiki/Tetrazole" title="Tetrazole">Tetrazole</a> </td></tr> <tr> <td>3 Nitrogen + Oxygen </td> <td> </td> <td><a href="/w/index.php?title=Oxatriazole&action=edit&redlink=1" class="new" title="Oxatriazole (page does not exist)">Oxatriazole</a> </td></tr> <tr> <td>3 Nitrogen + Sulfur </td> <td> </td> <td><a href="/w/index.php?title=Thiatriazole&action=edit&redlink=1" class="new" title="Thiatriazole (page does not exist)">Thiatriazole</a> </td></tr> <tr> <th colspan="3">Five-membered rings with five heteroatoms </th></tr> <tr> <th>Heteroatoms </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>5 × Nitrogen </td> <td> </td> <td><a href="/wiki/Pentazole" title="Pentazole">Pentazole</a> </td></tr> <tr> <td>4 Nitrogen + Oxygen </td> <td> </td> <td><a href="/wiki/Oxatetrazole" class="mw-redirect" title="Oxatetrazole">Oxatetrazole</a> </td></tr> <tr> <td>4 Nitrogen + Sulfur </td> <td> </td> <td><a href="/wiki/Thiatetrazole" class="mw-redirect" title="Thiatetrazole">Thiatetrazole</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="6-membered_rings">6-membered rings</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=7" title="Edit section: 6-membered rings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The 6-membered ring compounds containing <i>two</i> heteroatoms, at least one of which is nitrogen, are collectively called the <a href="/wiki/Azine_(heterocycle)" title="Azine (heterocycle)">azines</a>. <a href="/wiki/Thiazine" title="Thiazine">Thiazines</a> contain a sulfur and a nitrogen atom in the ring. <a href="/wiki/Dithiin" title="Dithiin">Dithiines</a> have two sulfur atoms. </p> <table class="wikitable"> <tbody><tr> <th colspan="4">Six-membered rings with one heteroatom </th></tr> <tr> <th>Heteroatom </th> <th>Saturated </th> <th>Unsaturated </th> <th>Ions </th></tr> <tr> <td><a href="/wiki/Antimony" title="Antimony">Antimony</a> </td> <td><a href="/w/index.php?title=Stibinane&action=edit&redlink=1" class="new" title="Stibinane (page does not exist)">Stibinane</a> </td> <td><a href="/w/index.php?title=Stibinine&action=edit&redlink=1" class="new" title="Stibinine (page does not exist)">Stibinine</a><sup id="cite_ref-C5H5Sb_7-0" class="reference"><a href="#cite_note-C5H5Sb-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td> <td><a href="/w/index.php?title=Stibatabenzene&action=edit&redlink=1" class="new" title="Stibatabenzene (page does not exist)">Stibatabenzene</a> cation </td></tr> <tr> <td><a href="/wiki/Arsenic" title="Arsenic">Arsenic</a> </td> <td><a href="/w/index.php?title=Arsinane&action=edit&redlink=1" class="new" title="Arsinane (page does not exist)">Arsinane</a> </td> <td><a href="/wiki/Arsinine" class="mw-redirect" title="Arsinine">Arsinine</a> </td> <td><a href="/w/index.php?title=Arsatabenzene&action=edit&redlink=1" class="new" title="Arsatabenzene (page does not exist)">Arsatabenzene</a> cation </td></tr> <tr> <td><a href="/wiki/Bismuth" title="Bismuth">Bismuth</a> </td> <td><a href="/w/index.php?title=Bisminane&action=edit&redlink=1" class="new" title="Bisminane (page does not exist)">Bisminane</a> </td> <td><a href="/wiki/Bismine" class="mw-redirect" title="Bismine">Bismine</a><sup id="cite_ref-C5H5Bi_8-0" class="reference"><a href="#cite_note-C5H5Bi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </td> <td><a href="/w/index.php?title=Bismatabenzene&action=edit&redlink=1" class="new" title="Bismatabenzene (page does not exist)">Bismatabenzene</a> cation </td></tr> <tr> <td><a href="/wiki/Boron" title="Boron">Boron</a> </td> <td><a href="/w/index.php?title=Borinane&action=edit&redlink=1" class="new" title="Borinane (page does not exist)">Borinane</a> </td> <td><a href="/wiki/Borinine" class="mw-redirect" title="Borinine">Borinine</a> </td> <td><a href="/wiki/Boratabenzene" title="Boratabenzene">Boratabenzene</a> anion </td></tr> <tr> <td><a href="/wiki/Germanium" title="Germanium">Germanium</a> </td> <td><a href="/w/index.php?title=Germinane&action=edit&redlink=1" class="new" title="Germinane (page does not exist)">Germinane</a> </td> <td><a href="/wiki/Germine" class="mw-redirect" title="Germine">Germine</a> </td> <td> </td></tr> <tr> <td><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> </td> <td><i><a href="/wiki/Piperidine" title="Piperidine">Piperidine</a></i><br />(<a href="/wiki/Azinane" class="mw-redirect" title="Azinane">Azinane</a> not used) </td> <td><i><a href="/wiki/Pyridine" title="Pyridine">Pyridine</a></i><br />(<a href="/wiki/Azine_(heterocycle)" title="Azine (heterocycle)">Azine</a> not used) </td> <td><a href="/wiki/Pyridinium" title="Pyridinium">Pyridinium</a> cation </td></tr> <tr> <td><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> </td> <td><a href="/wiki/Oxane" class="mw-redirect" title="Oxane">Oxane</a> </td> <td><i><a href="/wiki/Pyran" title="Pyran">Pyran</a></i><br />(<a href="/wiki/Oxine" class="mw-redirect" title="Oxine">Oxine</a> not used) </td> <td><a href="/wiki/Pyrylium" title="Pyrylium">Pyrylium</a> cation </td></tr> <tr> <td><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a> </td> <td><a href="/wiki/Phosphinane" title="Phosphinane">Phosphinane</a> </td> <td><a href="/wiki/Phosphinine" class="mw-redirect" title="Phosphinine">Phosphinine</a> </td> <td><a href="/w/index.php?title=Phosphatabenzene&action=edit&redlink=1" class="new" title="Phosphatabenzene (page does not exist)">Phosphatabenzene</a> cation </td></tr> <tr> <td><a href="/wiki/Selenium" title="Selenium">Selenium</a> </td> <td><a href="/w/index.php?title=Selenane&action=edit&redlink=1" class="new" title="Selenane (page does not exist)">Selenane</a> </td> <td><a href="/w/index.php?title=Selenopyran&action=edit&redlink=1" class="new" title="Selenopyran (page does not exist)">Selenopyran</a><sup id="cite_ref-C5H5Se+_9-0" class="reference"><a href="#cite_note-C5H5Se+-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </td> <td><a href="/wiki/Selenopyrylium" title="Selenopyrylium">Selenopyrylium</a> cation </td></tr> <tr> <td><a href="/wiki/Silicon" title="Silicon">Silicon</a> </td> <td><a href="/w/index.php?title=Silinane&action=edit&redlink=1" class="new" title="Silinane (page does not exist)">Silinane</a> </td> <td><a href="/wiki/Siline" class="mw-redirect" title="Siline">Siline</a> </td> <td> </td></tr> <tr> <td><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a> </td> <td><a href="/wiki/Thiane" title="Thiane">Thiane</a> </td> <td><i><a href="/wiki/Thiopyran" title="Thiopyran">Thiopyran</a></i><br />(<a href="/w/index.php?title=Thiine&action=edit&redlink=1" class="new" title="Thiine (page does not exist)">Thiine</a> not used) </td> <td><a href="/wiki/Thiopyrylium" title="Thiopyrylium">Thiopyrylium</a> cation </td></tr> <tr> <td><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a> </td> <td><a href="/w/index.php?title=Tellurane&action=edit&redlink=1" class="new" title="Tellurane (page does not exist)">Tellurane</a> </td> <td><a href="/w/index.php?title=Telluropyran&action=edit&redlink=1" class="new" title="Telluropyran (page does not exist)">Telluropyran</a> </td> <td><a href="/wiki/Telluropyrylium" title="Telluropyrylium">Telluropyrylium</a> cation </td></tr> <tr> <td><a href="/wiki/Tin" title="Tin">Tin</a> </td> <td><a href="/w/index.php?title=Stanninane&action=edit&redlink=1" class="new" title="Stanninane (page does not exist)">Stanninane</a> </td> <td><a href="/wiki/Stannine" class="mw-redirect" title="Stannine">Stannine</a> </td> <td> </td></tr> <tr> <th colspan="3">Six-membered rings with two heteroatoms </th></tr> <tr> <th>Heteroatoms </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>2 × Nitrogen </td> <td><i><a href="/wiki/Piperazine" title="Piperazine">Piperazine</a></i> </td> <td><i><a href="/wiki/Pyrazine" title="Pyrazine">Pyrazine</a></i><br /><i><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></i><br /><i><a href="/wiki/Pyridazine" title="Pyridazine">Pyridazine</a></i> </td></tr> <tr> <td>Nitrogen + Oxygen </td> <td><i><a href="/wiki/Morpholine" title="Morpholine">Morpholine</a></i> </td> <td><a href="/wiki/Oxazine" class="mw-redirect" title="Oxazine">Oxazine</a> </td></tr> <tr> <td>Nitrogen + Sulfur </td> <td><i><a href="/wiki/Thiomorpholine" title="Thiomorpholine">Thiomorpholine</a></i> </td> <td><a href="/wiki/Thiazine" title="Thiazine">Thiazine</a> </td></tr> <tr> <td>Oxygen + Sulfur </td> <td><a href="/wiki/Oxathiane" title="Oxathiane">Oxathiane</a> </td> <td><a href="/w/index.php?title=Oxathiin&action=edit&redlink=1" class="new" title="Oxathiin (page does not exist)">Oxathiin</a> </td></tr> <tr> <td>2 × Oxygen </td> <td><a href="/wiki/Dioxane" class="mw-redirect" title="Dioxane">Dioxane</a> </td> <td><a href="/wiki/Dioxin" title="Dioxin">Dioxin</a> </td></tr> <tr> <td>2 × Sulfur </td> <td><a href="/wiki/Dithiane" title="Dithiane">Dithiane</a> </td> <td><a href="/wiki/Dithiin" title="Dithiin">Dithiin</a> </td></tr> <tr> <th colspan="3">Six-membered rings with three heteroatoms </th></tr> <tr> <th>Heteroatoms </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>3 × Nitrogen </td> <td><a href="/wiki/Triazinane" title="Triazinane">Triazinane</a> </td> <td><a href="/wiki/Triazine" title="Triazine">Triazine</a> </td></tr> <tr> <td>3 × Oxygen </td> <td><a href="/wiki/Trioxane" title="Trioxane">Trioxane</a> </td> <td><a href="/wiki/Trioxin" class="mw-redirect" title="Trioxin">Trioxin</a> </td></tr> <tr> <td>3 × Sulfur </td> <td><a href="/wiki/Trithiane" class="mw-redirect" title="Trithiane">Trithiane</a> </td> <td><a href="/w/index.php?title=Trithiin&action=edit&redlink=1" class="new" title="Trithiin (page does not exist)">Trithiin</a> </td></tr> <tr> <th colspan="3">Six-membered rings with four heteroatoms </th></tr> <tr> <th>Heteroatoms </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>4 × Nitrogen </td> <td> </td> <td><a href="/wiki/Tetrazine" title="Tetrazine">Tetrazine</a> </td></tr> <tr> <td>2 Nitrogen + 2 Boron</td> <td></td> <td><a href="/wiki/Carborazine" title="Carborazine">Carborazine</a> </td></tr></tbody></table> <p><b>Six-membered rings with five heteroatoms</b><br />The <a href="/wiki/Hypothetical_chemical_compound" title="Hypothetical chemical compound">hypothetical chemical compound</a> with five nitrogen heteroatoms would be <a href="/wiki/Pentazine" title="Pentazine">pentazine</a>. </p><p><b>Six-membered rings with six heteroatoms</b><br />The <a href="/wiki/Hypothetical_chemical_compound" title="Hypothetical chemical compound">hypothetical chemical compound</a> with six nitrogen heteroatoms would be <a href="/wiki/Hexazine" title="Hexazine">hexazine</a>. <a href="/wiki/Borazine" title="Borazine">Borazine</a> is a six-membered ring with three nitrogen heteroatoms and three boron heteroatoms. </p> <div class="mw-heading mw-heading2"><h2 id="7-membered_rings">7-membered rings</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=8" title="Edit section: 7-membered rings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In a 7-membered ring, the heteroatom must be able to provide an empty π-orbital (e.g. boron) for "normal" aromatic stabilization to be available; otherwise, <a href="/wiki/Homoaromaticity" title="Homoaromaticity">homoaromaticity</a> may be possible. </p> <table class="wikitable"> <tbody><tr> <th colspan="3">Seven-membered rings with one heteroatom </th></tr> <tr> <th>Heteroatom </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>Boron </td> <td><a href="/w/index.php?title=Borepane&action=edit&redlink=1" class="new" title="Borepane (page does not exist)">Borepane</a> </td> <td><a href="/wiki/Borepine" class="mw-redirect" title="Borepine">Borepine</a> </td></tr> <tr> <td>Nitrogen </td> <td><a href="/wiki/Azepane" title="Azepane">Azepane</a> </td> <td><a href="/wiki/Azepine" title="Azepine">Azepine</a> </td></tr> <tr> <td>Oxygen </td> <td><a href="/wiki/Oxepane" title="Oxepane">Oxepane</a> </td> <td><a href="/wiki/Oxepine" class="mw-redirect" title="Oxepine">Oxepine</a> </td></tr> <tr> <td>Phosphorus </td> <td><a href="/w/index.php?title=Phosphepane&action=edit&redlink=1" class="new" title="Phosphepane (page does not exist)">Phosphepane</a> </td> <td><a href="/w/index.php?title=Phosphepine&action=edit&redlink=1" class="new" title="Phosphepine (page does not exist)">Phosphepine</a> </td></tr> <tr> <td>Sulfur </td> <td><a href="/wiki/Thiepane" title="Thiepane">Thiepane</a> </td> <td><a href="/wiki/Thiepine" title="Thiepine">Thiepine</a> </td></tr> <tr> <th colspan="3">Seven-membered rings with two heteroatoms </th></tr> <tr> <th>Heteroatoms </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>2 × Nitrogen </td> <td><a href="/w/index.php?title=Diazepane&action=edit&redlink=1" class="new" title="Diazepane (page does not exist)">Diazepane</a> </td> <td><a href="/wiki/Diazepine" title="Diazepine">Diazepine</a> </td></tr> <tr> <td>Nitrogen + Oxygen </td> <td><a href="/w/index.php?title=Oxazepane&action=edit&redlink=1" class="new" title="Oxazepane (page does not exist)">Oxazepane</a> </td> <td><a href="/wiki/Oxazepine" title="Oxazepine">Oxazepine</a> </td></tr> <tr> <td>Nitrogen + Sulfur </td> <td><a href="/w/index.php?title=Thiazepane&action=edit&redlink=1" class="new" title="Thiazepane (page does not exist)">Thiazepane</a> </td> <td><a href="/wiki/Thiazepine" title="Thiazepine">Thiazepine</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="8-membered_rings">8-membered rings</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=9" title="Edit section: 8-membered rings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <tbody><tr> <th>Heteroatom </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>Nitrogen </td> <td><a href="/wiki/Azocane" title="Azocane">Azocane</a> </td> <td><a href="/wiki/Azocine" title="Azocine">Azocine</a> </td></tr> <tr> <td>Oxygen </td> <td><a href="/w/index.php?title=Oxocane&action=edit&redlink=1" class="new" title="Oxocane (page does not exist)">Oxocane</a> </td> <td><a href="/w/index.php?title=Oxocine&action=edit&redlink=1" class="new" title="Oxocine (page does not exist)">Oxocine</a> </td></tr> <tr> <td>Sulfur </td> <td><a href="/w/index.php?title=Thiocane&action=edit&redlink=1" class="new" title="Thiocane (page does not exist)">Thiocane</a> </td> <td><a href="/w/index.php?title=Thiocine&action=edit&redlink=1" class="new" title="Thiocine (page does not exist)">Thiocine</a> </td></tr></tbody></table> <p><a href="/wiki/Borazocine" title="Borazocine">Borazocine</a> is a eight-membered ring with four nitrogen heteroatoms and four boron heteroatoms. </p> <div class="mw-heading mw-heading2"><h2 id="9-membered_rings">9-membered rings</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=10" title="Edit section: 9-membered rings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <tbody><tr> <th>Heteroatom </th> <th>Saturated </th> <th>Unsaturated </th></tr> <tr> <td>Nitrogen </td> <td><a href="/w/index.php?title=Azonane&action=edit&redlink=1" class="new" title="Azonane (page does not exist)">Azonane</a> </td> <td><a href="/wiki/Azonine" title="Azonine">Azonine</a> </td></tr> <tr> <td>Oxygen </td> <td><a href="/w/index.php?title=Oxonane&action=edit&redlink=1" class="new" title="Oxonane (page does not exist)">Oxonane</a> </td> <td><a href="/wiki/Oxonine" title="Oxonine">Oxonine</a> </td></tr> <tr> <td>Sulfur </td> <td><a href="/w/index.php?title=Thionane&action=edit&redlink=1" class="new" title="Thionane (page does not exist)">Thionane</a> </td> <td><a href="/wiki/(2Z,4Z,6Z,8Z)-Thionine" title="(2Z,4Z,6Z,8Z)-Thionine">Thionine</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Images_of_rings_with_one_heteroatom">Images of rings with one heteroatom</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=11" title="Edit section: Images of rings with one heteroatom"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <tbody><tr> <th colspan="1"></th> <th colspan="3">Saturated</th> <th colspan="3">Unsaturated </th></tr> <tr> <th align="left">Heteroatom</th> <th><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th> <th><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a></th> <th><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th> <th>Nitrogen</th> <th>Oxygen</th> <th>Sulfur </th></tr> <tr> <th rowspan="2">3-atom ring </th> <td><a href="/wiki/Aziridine" title="Aziridine">Aziridine</a></td> <td><a href="/wiki/Oxirane" class="mw-redirect" title="Oxirane">Oxirane</a></td> <td><a href="/wiki/Thiirane" title="Thiirane">Thiirane</a></td> <td><a href="/wiki/Azirine" title="Azirine">Azirine</a></td> <td><a href="/wiki/Oxirene" title="Oxirene">Oxirene</a></td> <td><a href="/wiki/Thiirene" title="Thiirene">Thiirene</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Aziridin.svg" class="mw-file-description" title="Structure of aziridine"><img alt="Structure of aziridine" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Aziridin.svg/60px-Aziridin.svg.png" decoding="async" width="60" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Aziridin.svg/90px-Aziridin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Aziridin.svg/120px-Aziridin.svg.png 2x" data-file-width="90" data-file-height="124" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Ethylene_oxide.svg" class="mw-file-description" title="Structure of oxirane"><img alt="Structure of oxirane" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Ethylene_oxide.svg/60px-Ethylene_oxide.svg.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Ethylene_oxide.svg/90px-Ethylene_oxide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/14/Ethylene_oxide.svg/120px-Ethylene_oxide.svg.png 2x" data-file-width="72" data-file-height="75" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Thiiran.svg" class="mw-file-description" title="Structure of thiirane"><img alt="Structure of thiirane" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Thiiran.svg/60px-Thiiran.svg.png" decoding="async" width="60" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Thiiran.svg/90px-Thiiran.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Thiiran.svg/120px-Thiiran.svg.png 2x" data-file-width="90" data-file-height="93" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Azirin.svg" class="mw-file-description" title="Structure of azirine"><img alt="Structure of azirine" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Azirin.svg/60px-Azirin.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Azirin.svg/90px-Azirin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Azirin.svg/120px-Azirin.svg.png 2x" data-file-width="89" data-file-height="89" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Oxiren.svg" class="mw-file-description" title="Structure of oxirene"><img alt="Structure of oxirene" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Oxiren.svg/60px-Oxiren.svg.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Oxiren.svg/90px-Oxiren.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/02/Oxiren.svg/120px-Oxiren.svg.png 2x" data-file-width="90" data-file-height="94" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Thiiren.svg" class="mw-file-description" title="Structure of thiirene"><img alt="Structure of thiirene" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Thiiren.svg/60px-Thiiren.svg.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Thiiren.svg/90px-Thiiren.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Thiiren.svg/120px-Thiiren.svg.png 2x" data-file-width="89" data-file-height="93" /></a></span> </td></tr> <tr> <th rowspan="2">4-atom ring </th> <td><a href="/wiki/Azetidine" title="Azetidine">Azetidine</a></td> <td><a href="/wiki/Oxetane" title="Oxetane">Oxetane</a></td> <td><a href="/wiki/Thietane" title="Thietane">Thietane</a></td> <td><a href="/wiki/Azete" title="Azete">Azete</a></td> <td><a href="/wiki/Oxete" class="mw-redirect" title="Oxete">Oxete</a></td> <td><a href="/wiki/Thiete" title="Thiete">Thiete</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Azetidine_structure.svg" class="mw-file-description" title="Structure of acetidine"><img alt="Structure of acetidine" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Azetidine_structure.svg/70px-Azetidine_structure.svg.png" decoding="async" width="70" height="55" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Azetidine_structure.svg/105px-Azetidine_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Azetidine_structure.svg/140px-Azetidine_structure.svg.png 2x" data-file-width="380" data-file-height="298" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Oxetan.png" class="mw-file-description" title="Structure of oxetane"><img alt="Structure of oxetane" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Oxetan.png/60px-Oxetan.png" decoding="async" width="60" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Oxetan.png/90px-Oxetan.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/Oxetan.png/120px-Oxetan.png 2x" data-file-width="628" data-file-height="648" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Thietan.png" class="mw-file-description" title="Structure of thietane"><img alt="Structure of thietane" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Thietan.png/60px-Thietan.png" decoding="async" width="60" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Thietan.png/90px-Thietan.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Thietan.png/120px-Thietan.png 2x" data-file-width="653" data-file-height="677" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Azete_structure.svg" class="mw-file-description" title="Structure of azete"><img alt="Structure of azete" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Azete_structure.svg/60px-Azete_structure.svg.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Azete_structure.svg/90px-Azete_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Azete_structure.svg/120px-Azete_structure.svg.png 2x" data-file-width="290" data-file-height="305" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Oxetene.svg" class="mw-file-description" title="Structure of oxete"><img alt="Structure of oxete" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Oxetene.svg/70px-Oxetene.svg.png" decoding="async" width="70" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Oxetene.svg/105px-Oxetene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/36/Oxetene.svg/140px-Oxetene.svg.png 2x" data-file-width="105" data-file-height="115" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Thietene.png" class="mw-file-description" title="Structure of thiete"><img alt="Structure of thiete" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Thietene.png/70px-Thietene.png" decoding="async" width="70" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Thietene.png/105px-Thietene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/66/Thietene.png/140px-Thietene.png 2x" data-file-width="392" data-file-height="413" /></a></span> </td></tr> <tr> <th rowspan="2">5-atom ring </th> <td><i><a href="/wiki/Pyrrolidine" title="Pyrrolidine">Pyrrolidine</a></i></td> <td><a href="/wiki/Oxolane" class="mw-redirect" title="Oxolane">Oxolane</a></td> <td><a href="/wiki/Thiolane" class="mw-redirect" title="Thiolane">Thiolane</a></td> <td><i><a href="/wiki/Pyrrole" title="Pyrrole">Pyrrole</a></i></td> <td><i><a href="/wiki/Furan" title="Furan">Furan</a></i></td> <td><i><a href="/wiki/Thiophene" title="Thiophene">Thiophene</a></i> </td></tr> <tr valign="top"> <td><span typeof="mw:File"><a href="/wiki/File:Pyrrolidine-Structural_Formula_V.1.svg" class="mw-file-description" title="Structure of pyrrolidine"><img alt="Structure of pyrrolidine" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Pyrrolidine-Structural_Formula_V.1.svg/60px-Pyrrolidine-Structural_Formula_V.1.svg.png" decoding="async" width="60" height="81" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Pyrrolidine-Structural_Formula_V.1.svg/90px-Pyrrolidine-Structural_Formula_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/90/Pyrrolidine-Structural_Formula_V.1.svg/120px-Pyrrolidine-Structural_Formula_V.1.svg.png 2x" data-file-width="89" data-file-height="120" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Tetrahydrofuran_acsv.svg" class="mw-file-description" title="Structure of oxolane"><img alt="Structure of oxolane" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Tetrahydrofuran_acsv.svg/70px-Tetrahydrofuran_acsv.svg.png" decoding="async" width="70" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Tetrahydrofuran_acsv.svg/105px-Tetrahydrofuran_acsv.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Tetrahydrofuran_acsv.svg/140px-Tetrahydrofuran_acsv.svg.png 2x" data-file-width="280" data-file-height="297" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Tetrahydrothiophen.png" class="mw-file-description" title="Structure of thiolane"><img alt="Structure of thiolane" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Tetrahydrothiophen.png/70px-Tetrahydrothiophen.png" decoding="async" width="70" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Tetrahydrothiophen.png/105px-Tetrahydrothiophen.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Tetrahydrothiophen.png/140px-Tetrahydrothiophen.png 2x" data-file-width="1066" data-file-height="1154" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Pyrrol2.svg" class="mw-file-description" title="Structure of pyrrole"><img alt="Structure of pyrrole" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Pyrrol2.svg/70px-Pyrrol2.svg.png" decoding="async" width="70" height="97" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Pyrrol2.svg/105px-Pyrrol2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Pyrrol2.svg/140px-Pyrrol2.svg.png 2x" data-file-width="66" data-file-height="91" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Furan.svg" class="mw-file-description" title="Structure of furan"><img alt="Structure of furan" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Furan.svg/70px-Furan.svg.png" decoding="async" width="70" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Furan.svg/105px-Furan.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/35/Furan.svg/140px-Furan.svg.png 2x" data-file-width="66" data-file-height="72" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Thiophen.svg" class="mw-file-description" title="Structure of thiophene"><img alt="Structure of thiophene" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Thiophen.svg/70px-Thiophen.svg.png" decoding="async" width="70" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Thiophen.svg/105px-Thiophen.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/Thiophen.svg/140px-Thiophen.svg.png 2x" data-file-width="66" data-file-height="72" /></a></span> </td></tr> <tr> <th rowspan="2">6-atom ring </th> <td><i><a href="/wiki/Piperidine" title="Piperidine">Piperidine</a></i></td> <td><a href="/wiki/Oxane" class="mw-redirect" title="Oxane">Oxane</a></td> <td><a href="/wiki/Thiane" title="Thiane">Thiane</a></td> <td><i><a href="/wiki/Pyridine" title="Pyridine">Pyridine</a></i></td> <td><i><a href="/wiki/Pyran" title="Pyran">Pyran</a></i></td> <td><i><a href="/wiki/Thiopyran" title="Thiopyran">Thiopyran</a></i> </td></tr> <tr valign="top"> <td><span typeof="mw:File"><a href="/wiki/File:Piperidin.svg" class="mw-file-description" title="Structure of piperidine"><img alt="Structure of piperidine" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Piperidin.svg/70px-Piperidin.svg.png" decoding="async" width="70" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/Piperidin.svg/105px-Piperidin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/54/Piperidin.svg/140px-Piperidin.svg.png 2x" data-file-width="70" data-file-height="110" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Tetrahydropyran_(vzorec).svg" class="mw-file-description" title="Structure of oxane"><img alt="Structure of oxane" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Tetrahydropyran_%28vzorec%29.svg/70px-Tetrahydropyran_%28vzorec%29.svg.png" decoding="async" width="70" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Tetrahydropyran_%28vzorec%29.svg/105px-Tetrahydropyran_%28vzorec%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/Tetrahydropyran_%28vzorec%29.svg/140px-Tetrahydropyran_%28vzorec%29.svg.png 2x" data-file-width="95" data-file-height="118" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Thiane3.svg" class="mw-file-description" title="Structure of thiane"><img alt="Structure of thiane" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Thiane3.svg/70px-Thiane3.svg.png" decoding="async" width="70" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Thiane3.svg/105px-Thiane3.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/df/Thiane3.svg/140px-Thiane3.svg.png 2x" data-file-width="98" data-file-height="126" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Pyridin.svg" class="mw-file-description" title="Structure of pyridine"><img alt="Structure of pyridine" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Pyridin.svg/70px-Pyridin.svg.png" decoding="async" width="70" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Pyridin.svg/105px-Pyridin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Pyridin.svg/140px-Pyridin.svg.png 2x" data-file-width="70" data-file-height="90" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Pyran.svg" class="mw-file-description" title="Structure of pyran"><img alt="Structure of pyran" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Pyran.svg/70px-Pyran.svg.png" decoding="async" width="70" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Pyran.svg/105px-Pyran.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Pyran.svg/140px-Pyran.svg.png 2x" data-file-width="94" data-file-height="118" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:1,2-Thiapyran.svg" class="mw-file-description" title="Structure of thiopyran"><img alt="Structure of thiopyran" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/1%2C2-Thiapyran.svg/70px-1%2C2-Thiapyran.svg.png" decoding="async" width="70" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/1%2C2-Thiapyran.svg/105px-1%2C2-Thiapyran.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b6/1%2C2-Thiapyran.svg/140px-1%2C2-Thiapyran.svg.png 2x" data-file-width="41" data-file-height="53" /></a></span> </td></tr> <tr> <th rowspan="2">7-atom ring </th> <td><a href="/wiki/Azepane" title="Azepane">Azepane</a></td> <td><a href="/wiki/Oxepane" title="Oxepane">Oxepane</a></td> <td><a href="/wiki/Thiepane" title="Thiepane">Thiepane</a></td> <td><a href="/wiki/Azepine" title="Azepine">Azepine</a></td> <td><a href="/wiki/Oxepine" class="mw-redirect" title="Oxepine">Oxepine</a></td> <td><a href="/wiki/Thiepine" title="Thiepine">Thiepine</a> </td></tr> <tr valign="bottom"> <td><span typeof="mw:File"><a href="/wiki/File:Azepane.svg" class="mw-file-description" title="Structure of azepane"><img alt="Structure of azepane" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Azepane.svg/70px-Azepane.svg.png" decoding="async" width="70" height="97" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Azepane.svg/105px-Azepane.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Azepane.svg/140px-Azepane.svg.png 2x" data-file-width="180" data-file-height="250" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Oxepan.png" class="mw-file-description" title="Structure of oxepane"><img alt="Structure of oxepane" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Oxepan.png/70px-Oxepan.png" decoding="async" width="70" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Oxepan.png/105px-Oxepan.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/Oxepan.png/140px-Oxepan.png 2x" data-file-width="1098" data-file-height="1174" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Thiepan.svg" class="mw-file-description" title="Structure of thiepane"><img alt="Structure of thiepane" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Thiepan.svg/70px-Thiepan.svg.png" decoding="async" width="70" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Thiepan.svg/105px-Thiepan.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Thiepan.svg/140px-Thiepan.svg.png 2x" data-file-width="128" data-file-height="128" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Azepine-2D-skeletal.png" class="mw-file-description" title="Structure of azepine"><img alt="Structure of azepine" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Azepine-2D-skeletal.png/70px-Azepine-2D-skeletal.png" decoding="async" width="70" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Azepine-2D-skeletal.png/105px-Azepine-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Azepine-2D-skeletal.png/140px-Azepine-2D-skeletal.png 2x" data-file-width="876" data-file-height="1100" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Oxepine.svg" class="mw-file-description" title="Structure of oxepine"><img alt="Structure of oxepine" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Oxepine.svg/70px-Oxepine.svg.png" decoding="async" width="70" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Oxepine.svg/105px-Oxepine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/49/Oxepine.svg/140px-Oxepine.svg.png 2x" data-file-width="220" data-file-height="232" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Thiepine.png" class="mw-file-description" title="Structure of thiepine"><img alt="Structure of thiepine" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Thiepine.png/70px-Thiepine.png" decoding="async" width="70" height="73" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Thiepine.png/105px-Thiepine.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/49/Thiepine.png/140px-Thiepine.png 2x" data-file-width="347" data-file-height="362" /></a></span> </td></tr> <tr> <th rowspan="2">8-atom ring </th> <td><a href="/wiki/Azocane" title="Azocane">Azocane</a></td> <td><a href="/w/index.php?title=Oxocane&action=edit&redlink=1" class="new" title="Oxocane (page does not exist)">Oxocane</a></td> <td><a href="/w/index.php?title=Thiocane&action=edit&redlink=1" class="new" title="Thiocane (page does not exist)">Thiocane</a></td> <td><a href="/wiki/Azocine" title="Azocine">Azocine</a></td> <td><a href="/w/index.php?title=Oxocine&action=edit&redlink=1" class="new" title="Oxocine (page does not exist)">Oxocine</a></td> <td><a href="/w/index.php?title=Thiocine&action=edit&redlink=1" class="new" title="Thiocine (page does not exist)">Thiocine</a> </td></tr> <tr valign="bottom"> <td><span typeof="mw:File"><a href="/wiki/File:Azocane.png" class="mw-file-description" title="Structure of azocane"><img alt="Structure of azocane" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Azocane.png/70px-Azocane.png" decoding="async" width="70" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Azocane.png/105px-Azocane.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Azocane.png/140px-Azocane.png 2x" data-file-width="814" data-file-height="1048" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Oxocano.png" class="mw-file-description" title="Structure of oxocane"><img alt="Structure of oxocane" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Oxocano.png/70px-Oxocano.png" decoding="async" width="70" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Oxocano.png/105px-Oxocano.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/86/Oxocano.png/140px-Oxocano.png 2x" data-file-width="708" data-file-height="751" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Tiocano.png" class="mw-file-description" title="Structure of thiocane"><img alt="Structure of thiocane" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Tiocano.png/70px-Tiocano.png" decoding="async" width="70" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Tiocano.png/105px-Tiocano.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/72/Tiocano.png/140px-Tiocano.png 2x" data-file-width="708" data-file-height="751" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Azocine.png" class="mw-file-description" title="Structure of azocine"><img alt="Structure of azocine" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Azocine.png/70px-Azocine.png" decoding="async" width="70" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Azocine.png/105px-Azocine.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Azocine.png/140px-Azocine.png 2x" data-file-width="814" data-file-height="875" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Oxocinio.png" class="mw-file-description" title="Structure of oxocine"><img alt="Structure of oxocine" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Oxocinio.png/70px-Oxocinio.png" decoding="async" width="70" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Oxocinio.png/105px-Oxocinio.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Oxocinio.png/140px-Oxocinio.png 2x" data-file-width="708" data-file-height="751" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Tiocinio.png" class="mw-file-description" title="Structure of thiocine"><img alt="Structure of thiocine" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Tiocinio.png/70px-Tiocinio.png" decoding="async" width="70" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Tiocinio.png/105px-Tiocinio.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Tiocinio.png/140px-Tiocinio.png 2x" data-file-width="708" data-file-height="751" /></a></span> </td></tr> <tr> <th rowspan="2">9-atom ring </th> <td><a href="/w/index.php?title=Azonane&action=edit&redlink=1" class="new" title="Azonane (page does not exist)">Azonane</a></td> <td><a href="/w/index.php?title=Oxonane&action=edit&redlink=1" class="new" title="Oxonane (page does not exist)">Oxonane</a></td> <td><a href="/w/index.php?title=Thionane&action=edit&redlink=1" class="new" title="Thionane (page does not exist)">Thionane</a></td> <td><a href="/wiki/Azonine" title="Azonine">Azonine</a></td> <td><a href="/wiki/Oxonine" title="Oxonine">Oxonine</a></td> <td><a href="/wiki/(2Z,4Z,6Z,8Z)-Thionine" title="(2Z,4Z,6Z,8Z)-Thionine">Thionine</a> </td></tr> <tr valign="bottom"> <td><span typeof="mw:File"><a href="/wiki/File:Azonano.png" class="mw-file-description" title="Structure of azonane"><img alt="Structure of azonane" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Azonano.png/70px-Azonano.png" decoding="async" width="70" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Azonano.png/105px-Azonano.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/68/Azonano.png/140px-Azonano.png 2x" data-file-width="1831" data-file-height="2280" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Oxonano.png" class="mw-file-description" title="Structure of oxonane"><img alt="Structure of oxonane" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/Oxonano.png/70px-Oxonano.png" decoding="async" width="70" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/Oxonano.png/105px-Oxonano.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a7/Oxonano.png/140px-Oxonano.png 2x" data-file-width="1831" data-file-height="1936" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Tionano.png" class="mw-file-description" title="Structure of thionane"><img alt="Structure of thionane" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/Tionano.png/70px-Tionano.png" decoding="async" width="70" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/Tionano.png/105px-Tionano.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/Tionano.png/140px-Tionano.png 2x" data-file-width="1831" data-file-height="1936" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Azonina.png" class="mw-file-description" title="Structure of azonine"><img alt="Structure of azonine" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Azonina.png/70px-Azonina.png" decoding="async" width="70" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Azonina.png/105px-Azonina.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/Azonina.png/140px-Azonina.png 2x" data-file-width="1831" data-file-height="2280" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Oxonina.png" class="mw-file-description" title="Structure of oxonine"><img alt="Structure of oxonine" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Oxonina.png/70px-Oxonina.png" decoding="async" width="70" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Oxonina.png/105px-Oxonina.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Oxonina.png/140px-Oxonina.png 2x" data-file-width="1831" data-file-height="1936" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Tionina.png" class="mw-file-description" title="Structure of thionine"><img alt="Structure of thionine" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Tionina.png/70px-Tionina.png" decoding="async" width="70" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Tionina.png/105px-Tionina.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Tionina.png/140px-Tionina.png 2x" data-file-width="1831" data-file-height="1936" /></a></span> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Fused/condensed_rings"><span id="Fused.2Fcondensed_rings"></span>Fused/condensed rings</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=12" title="Edit section: Fused/condensed rings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Heterocyclic rings systems that are formally derived by fusion with other rings, either <a href="/wiki/Carbocycle" class="mw-redirect" title="Carbocycle">carbocyclic</a> or heterocyclic, have a variety of common and systematic names. For example, with the benzo-fused unsaturated nitrogen heterocycles, pyrrole provides <a href="/wiki/Indole" title="Indole">indole</a> or <a href="/wiki/Isoindole" title="Isoindole">isoindole</a> depending on the orientation. The pyridine analog is <a href="/wiki/Quinoline" title="Quinoline">quinoline</a> or <a href="/wiki/Isoquinoline" title="Isoquinoline">isoquinoline</a>. For azepine, <a href="/wiki/Benzazepine" title="Benzazepine">benzazepine</a> is the preferred name. Likewise, the compounds with two benzene rings fused to the central heterocycle are <a href="/wiki/Carbazole" title="Carbazole">carbazole</a>, <a href="/wiki/Acridine" title="Acridine">acridine</a>, and dibenzoazepine. <a href="/wiki/Thienothiophene" title="Thienothiophene">Thienothiophene</a> are the fusion of two thiophene rings. <a href="/wiki/Phosphaphenalene" title="Phosphaphenalene">Phosphaphenalenes</a> are a tricyclic phosphorus-containing heterocyclic system derived from the carbocycle <a href="/wiki/Phenalene" title="Phenalene">phenalene</a>. </p> <div class="mw-heading mw-heading2"><h2 id="History_of_heterocyclic_chemistry">History of heterocyclic chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=13" title="Edit section: History of heterocyclic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The history of heterocyclic chemistry began in the 1800s, in step with the development of <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>. Some noteworthy developments:<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> </p> <ul><li>1818: Brugnatelli makes <a href="/wiki/Alloxan" title="Alloxan">alloxan</a> from <a href="/wiki/Uric_acid" title="Uric acid">uric acid</a></li> <li>1832: Dobereiner produces <a href="/wiki/Furfural" title="Furfural">furfural</a> (a furan) by treating <a href="/wiki/Starch" title="Starch">starch</a> with <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a></li> <li>1834: Runge obtains <a href="/wiki/Pyrrole" title="Pyrrole">pyrrole</a> ("fiery oil") by dry distillation of bones</li> <li>1906: Friedlander synthesizes <a href="/wiki/Indigo_dye" title="Indigo dye">indigo dye</a>, allowing synthetic chemistry to displace a large agricultural industry</li> <li>1936: <a href="/wiki/Alfred_E._Treibs" title="Alfred E. Treibs">Treibs</a> isolates chlorophyll derivatives from crude oil, explaining the biological origin of petroleum.</li> <li>1951: <a href="/wiki/Chargaff%27s_rules" title="Chargaff's rules">Chargaff's rules</a> are described, highlighting the role of heterocyclic compounds (<a href="/wiki/Purine" title="Purine">purines</a> and <a href="/wiki/Pyrimidine" title="Pyrimidine">pyrimidines</a>) in the genetic code.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=14" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Heterocyclic compounds are pervasive in many areas of life sciences and technology.<sup id="cite_ref-Gilchrist_2-1" class="reference"><a href="#cite_note-Gilchrist-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Many drugs are heterocyclic compounds.<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> </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=Heterocyclic_compound&action=edit&section=15" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Spiroketals" title="Spiroketals">Spiroketals</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterocyclic_compound&action=edit&section=16" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/wiki/IUPAC_Gold_Book" class="mw-redirect" title="IUPAC Gold Book">IUPAC Gold Book</a> <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/H02798.html"><i>heterocyclic compounds</i></a></span> </li> <li id="cite_note-Gilchrist-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Gilchrist_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Gilchrist_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Thomas L. Gilchrist "Heterocyclic Chemistry" 3rd ed. Addison Wesley: Essex, England, 1997. 414 pp. <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/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-582-27843-0" title="Special:BookSources/0-582-27843-0">0-582-27843-0</a>.</span> </li> <li id="cite_note-Rees-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Rees_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRees1992" class="citation journal cs1">Rees, Charles W. (1992). 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