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class="vector-toc-numb">5</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 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Available in 36 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-36" 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">36 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Arielgroep" title="Arielgroep – Afrikaans" lang="af" hreflang="af" data-title="Arielgroep" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D8%B1%D9%8A%D9%84_(%D9%83%D9%8A%D9%85%D9%8A%D8%A7%D8%A1)" title="أريل (كيمياء) – Arabic" lang="ar" hreflang="ar" data-title="أريل (كيمياء)" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D1%80%D1%8B%D0%BB" title="Арыл – Belarusian" lang="be" hreflang="be" data-title="Арыл" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%90%D1%80%D1%8B%D0%BB" title="Арыл – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Арыл" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Grup_aril" title="Grup aril – Catalan" lang="ca" hreflang="ca" data-title="Grup aril" 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/Aryl" title="Aryl – Czech" lang="cs" hreflang="cs" data-title="Aryl" 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/Aryl" title="Aryl – Danish" lang="da" hreflang="da" data-title="Aryl" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Arylgruppe" title="Arylgruppe – German" lang="de" hreflang="de" data-title="Arylgruppe" 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/Ar%C3%BC%C3%BClr%C3%BChm" title="Arüülrühm – Estonian" lang="et" hreflang="et" data-title="Arüülrühm" 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%91%CF%81%CF%8D%CE%BB%CE%B9%CE%B1" title="Αρύλια – Greek" lang="el" hreflang="el" data-title="Αρύλια" 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/Grupo_arilo" title="Grupo arilo – Spanish" lang="es" hreflang="es" data-title="Grupo arilo" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Arilo_(kimika)" title="Arilo (kimika) – Basque" lang="eu" hreflang="eu" data-title="Arilo (kimika)" 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%A2%D8%B1%DB%8C%D9%84_(%D9%85%D9%88%D8%A7%D8%AF_%D8%A2%D9%84%DB%8C)" title="آریل (مواد آلی) – Persian" lang="fa" hreflang="fa" data-title="آریل (مواد آلی)" 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/Aryle" title="Aryle – French" lang="fr" hreflang="fr" data-title="Aryle" 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/Gr%C3%BApa_airile" title="Grúpa airile – Irish" lang="ga" hreflang="ga" data-title="Grúpa airile" 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/Aril" title="Aril – Galician" lang="gl" hreflang="gl" data-title="Aril" 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/%EC%95%84%EB%A6%B4%EA%B8%B0" title="아릴기 – Korean" lang="ko" hreflang="ko" data-title="아릴기" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Aril" title="Aril – Indonesian" lang="id" hreflang="id" data-title="Aril" 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/Arile" title="Arile – Italian" lang="it" hreflang="it" data-title="Arile" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Arilcsoport" title="Arilcsoport – Hungarian" lang="hu" hreflang="hu" data-title="Arilcsoport" 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%90%D1%80%D0%B8%D0%BB" title="Арил – Macedonian" lang="mk" hreflang="mk" data-title="Арил" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Arylgroep" title="Arylgroep – Dutch" lang="nl" hreflang="nl" data-title="Arylgroep" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%AA%E3%83%BC%E3%83%AB%E5%9F%BA" title="アリール基 – Japanese" lang="ja" hreflang="ja" data-title="アリール基" 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/Aryl" title="Aryl – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Aryl" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Grupa_arylowa" title="Grupa arylowa – Polish" lang="pl" hreflang="pl" data-title="Grupa arylowa" 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/Arila" title="Arila – Portuguese" lang="pt" hreflang="pt" data-title="Arila" 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/Aril" title="Aril – Romanian" lang="ro" hreflang="ro" data-title="Aril" 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%90%D1%80%D0%B8%D0%BB%D1%8C%D0%BD%D0%B0%D1%8F_%D0%B3%D1%80%D1%83%D0%BF%D0%BF%D0%B0" title="Арильная группа – Russian" lang="ru" hreflang="ru" data-title="Арильная группа" 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/Arylov%C3%A1_skupina" title="Arylová skupina – Slovak" lang="sk" hreflang="sk" data-title="Arylová skupina" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Aril" title="Aril – Serbian" lang="sr" hreflang="sr" data-title="Aril" 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/Aril" title="Aril – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Aril" 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-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Arylgrupp" title="Arylgrupp – Swedish" lang="sv" hreflang="sv" data-title="Arylgrupp" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%85%E0%AE%B0%E0%AF%88%E0%AE%B2%E0%AF%8D" title="அரைல் – Tamil" lang="ta" hreflang="ta" data-title="அரைல்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D1%80%D0%B8%D0%BB" title="Арил – Ukrainian" lang="uk" hreflang="uk" data-title="Арил" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%8A%B3%E5%9F%BA" title="芳基 – Wu" lang="wuu" hreflang="wuu" 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div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the aryl organic functional group. For the covering of certain seeds, see <a href="/wiki/Aril" title="Aril">aril</a>.</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Phenyl-group.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Phenyl-group.svg/250px-Phenyl-group.svg.png" decoding="async" width="250" height="143" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Phenyl-group.svg/375px-Phenyl-group.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Phenyl-group.svg/500px-Phenyl-group.svg.png 2x" data-file-width="512" data-file-height="293" /></a><figcaption>A <a href="/wiki/Phenyl_group" title="Phenyl group">phenyl group</a> is the simplest <i>aryl group</i>, here bonded to an "R" group.</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, an <b>aryl</b> is any <a href="/wiki/Functional_group" title="Functional group">functional group</a> or <a href="/wiki/Substituent" title="Substituent">substituent</a> derived from an <a href="/wiki/Aromaticity" title="Aromaticity">aromatic ring</a>, usually an <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">aromatic hydrocarbon</a>, such as <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a> and <a href="/wiki/Naphthyl" class="mw-redirect" title="Naphthyl">naphthyl</a>.<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> "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as a placeholder for the aryl group in chemical structure diagrams, analogous to “R” used for any organic substituent. “Ar” is not to be confused with the elemental symbol for <a href="/wiki/Argon" title="Argon">argon</a>. </p><p>A simple aryl group is <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a> (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>−</span>), a group derived from <a href="/wiki/Benzene" title="Benzene">benzene</a>. Examples of other aryl groups consist of: </p> <ul><li>The <a href="/wiki/Tolyl_groups" class="mw-redirect" title="Tolyl groups">tolyl</a> group (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">4</sub>−</span>) which is derived from <a href="/wiki/Toluene" title="Toluene">toluene</a> (methylbenzene)</li> <li>The <a href="/wiki/Xylyl" class="mw-redirect" title="Xylyl">xylyl</a> group (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">3</sub>−</span>), which is derived from <a href="/wiki/Xylene" title="Xylene">xylene</a> (dimethylbenzene)</li> <li>The <a href="/wiki/Naphthyl" class="mw-redirect" title="Naphthyl">naphthyl</a> group (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">10</sub>H<sub class="template-chem2-sub">7</sub>−</span>), which is derived from <a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a></li></ul> <p><a href="/wiki/Arylation" class="mw-redirect" title="Arylation">Arylation</a> is the process in which an aryl group is attached to a substituent. It is typically achieved by <a href="/wiki/Cross-coupling_reaction" title="Cross-coupling reaction">cross-coupling reactions</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aryl_group&action=edit&section=1" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The simplest aryl group is <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a>, which is made up of a benzene ring with one of its hydrogen atom replaced by some substituent, and has the molecular formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>−</span>. Note that a phenyl group is not the same as a <a href="/wiki/Benzyl" class="mw-redirect" title="Benzyl">benzyl group</a>, the latter consisting of a phenyl group attached to a methyl group and a molecular formula of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CH<sub class="template-chem2-sub">2</sub>−</span>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Phenol-2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Phenol-2.svg/100px-Phenol-2.svg.png" decoding="async" width="100" height="173" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Phenol-2.svg/150px-Phenol-2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/Phenol-2.svg/200px-Phenol-2.svg.png 2x" data-file-width="77" data-file-height="133" /></a><figcaption>Phenol (or hydroxybenzene)</figcaption></figure> <p>To name compounds containing phenyl groups, the phenyl group can be taken to be the parent hydrocarbon and be represented by the suffix <span class="nowrap">"– benzene".</span> Alternatively, the phenyl group could be treated as the substituent, being described within the name as "phenyl". This is usually done when the group attached to the phenyl group consists of six or more carbon atoms.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>As an example, consider a hydroxyl group connected to a phenyl group. In this case, if the phenyl group were taken to be the parent hydrocarbon, the compound would be named hydroxybenzene. Alternatively, and more commonly, the hydroxyl group could be taken as the parent group and the phenyl group treated as the substituent, resulting in the more familiar name <a href="/wiki/Phenol" title="Phenol">phenol</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Aryl_group&action=edit&section=2" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Arene" class="mw-redirect" title="Arene">arene</a></div> <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=Aryl_group&action=edit&section=3" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a></li> <li><a href="/wiki/Aryl_hydrocarbon_receptor" title="Aryl hydrocarbon receptor">Aryl hydrocarbon receptor</a>, a bodily target for <a href="/wiki/Dioxins_and_dioxin-like_compounds" title="Dioxins and dioxin-like compounds">dioxins</a><sup id="cite_ref-pmid16545780_5-0" class="reference"><a href="#cite_note-pmid16545780-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Aryloxy" class="mw-redirect" title="Aryloxy">Aryloxy</a> group</li> <li><a href="/wiki/Arene_compound" class="mw-redirect" title="Arene compound">Arene compound</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=Aryl_group&action=edit&section=4" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/A00464.html">aryl groups</a>". <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.A00464">10.1351/goldbook.A00464</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCareySundberg2008" class="citation book cs1">Carey, Francis; Sundberg, Richard (2008). <i>Advanced Organic Chemistry, Part A: Structure and Mechanisms</i> (5th ed.). Springer.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%2C+Part+A%3A+Structure+and+Mechanisms&rft.edition=5th&rft.pub=Springer&rft.date=2008&rft.aulast=Carey&rft.aufirst=Francis&rft.au=Sundberg%2C+Richard&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAryl+group" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIUPAC,_Commission_on_Nomenclature_of_Organic_Chemistry1993" class="citation book cs1">IUPAC, Commission on Nomenclature of Organic Chemistry (1993). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140208214014/http://www.acdlabs.com/iupac/nomenclature/93/r93_671.htm"><i>A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993)</i></a>. Blackwell Scientific Publications. Archived from <a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/93/r93_671.htm">the original</a> on 2014-02-08<span class="reference-accessdate">. Retrieved <span class="nowrap">2017-10-26</span></span> – via acdlabs.com.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=A+Guide+to+IUPAC+Nomenclature+of+Organic+Compounds+%28Recommendations+1993%29&rft.pub=Blackwell+Scientific+Publications&rft.date=1993&rft.au=IUPAC%2C+Commission+on+Nomenclature+of+Organic+Chemistry&rft_id=http%3A%2F%2Fwww.acdlabs.com%2Fiupac%2Fnomenclature%2F93%2Fr93_671.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAryl+group" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBrown2018" class="citation book cs1">Brown, William Henry (2018). <a rel="nofollow" class="external text" href="https://www.worldcat.org/oclc/974377227"><i>Organic chemistry</i></a>. Brent L. Iverson, Eric V. Anslyn, Christopher S. Foote (8th ed.). Boston, MA. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-305-58035-0" title="Special:BookSources/978-1-305-58035-0"><bdi>978-1-305-58035-0</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/974377227">974377227</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+chemistry&rft.place=Boston%2C+MA&rft.edition=8th&rft.date=2018&rft_id=info%3Aoclcnum%2F974377227&rft.isbn=978-1-305-58035-0&rft.aulast=Brown&rft.aufirst=William+Henry&rft_id=https%3A%2F%2Fwww.worldcat.org%2Foclc%2F974377227&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAryl+group" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: location missing publisher (<a href="/wiki/Category:CS1_maint:_location_missing_publisher" title="Category:CS1 maint: location missing publisher">link</a>)</span></span> </li> <li id="cite_note-pmid16545780-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid16545780_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBock_KW,_Köhle_C2006" class="citation journal cs1">Bock KW, Köhle C (2006). "Ah receptor: dioxin-mediated toxic responses as hints to deregulated physiologic functions". <i>Biochem. Pharmacol</i>. <b>72</b> (4): 393–404. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.bcp.2006.01.017">10.1016/j.bcp.2006.01.017</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16545780">16545780</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochem.+Pharmacol.&rft.atitle=Ah+receptor%3A+dioxin-mediated+toxic+responses+as+hints+to+deregulated+physiologic+functions&rft.volume=72&rft.issue=4&rft.pages=393-404&rft.date=2006&rft_id=info%3Adoi%2F10.1016%2Fj.bcp.2006.01.017&rft_id=info%3Apmid%2F16545780&rft.au=Bock+KW%2C+K%C3%B6hle+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAryl+group" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 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