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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">Phenyl group</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 40 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-40" 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">40 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%AC%D9%85%D9%88%D8%B9%D8%A9_%D9%81%D9%8A%D9%86%D9%8A%D9%84" title="مجموعة فينيل – Arabic" lang="ar" hreflang="ar" data-title="مجموعة فينيل" 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%A4%D0%B5%D0%BD%D1%96%D0%BB%D1%8C%D0%BD%D0%B0%D1%8F_%D0%B3%D1%80%D1%83%D0%BF%D0%B0" title="Фенільная група – Belarusian" lang="be" hreflang="be" data-title="Фенільная група" 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%A4%D1%8D%D0%BD%D1%96%D0%BB%D1%8C%D0%BD%D0%B0%D1%8F_%D0%B3%D1%80%D1%83%D0%BF%D0%B0" title="Фэнільная група – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Фэнільная група" 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-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Fenil_grupa" title="Fenil grupa – Bosnian" lang="bs" hreflang="bs" data-title="Fenil grupa" 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/Grup_fenil" title="Grup fenil – Catalan" lang="ca" hreflang="ca" data-title="Grup fenil" 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/Fenyl" title="Fenyl – Czech" lang="cs" hreflang="cs" data-title="Fenyl" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Gr%C5%B5p_ffenyl" title="Grŵp ffenyl – Welsh" lang="cy" hreflang="cy" data-title="Grŵp ffenyl" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Fenylgruppe" title="Fenylgruppe – Danish" lang="da" hreflang="da" data-title="Fenylgruppe" 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/Phenylgruppe" title="Phenylgruppe – German" lang="de" hreflang="de" data-title="Phenylgruppe" 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/Fen%C3%BC%C3%BClr%C3%BChm" title="Fenüülrühm – Estonian" lang="et" hreflang="et" data-title="Fenüülrühm" 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%A6%CE%B1%CE%B9%CE%BD%CF%85%CE%BB%CE%BF%CE%BC%CE%AC%CE%B4%CE%B1" title="Φαινυλομάδα – Greek" lang="el" hreflang="el" data-title="Φαινυλομάδα" 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/Fenilo" title="Fenilo – Spanish" lang="es" hreflang="es" data-title="Fenilo" 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/Fenilo_taldea" title="Fenilo taldea – Basque" lang="eu" hreflang="eu" data-title="Fenilo taldea" 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/%DA%AF%D8%B1%D9%88%D9%87_%D9%81%D9%86%DB%8C%D9%84" title="گروه فنیل – Persian" lang="fa" hreflang="fa" data-title="گروه فنیل" 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/Ph%C3%A9nyle" title="Phényle – French" lang="fr" hreflang="fr" data-title="Phényle" 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/Feinil" title="Feinil – Irish" lang="ga" hreflang="ga" data-title="Feinil" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8E%98%EB%8B%90%EA%B8%B0" title="페닐기 – Korean" lang="ko" hreflang="ko" data-title="페닐기" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AB%E0%A4%BF%E0%A4%A8%E0%A4%BE%E0%A4%87%E0%A4%B2_%E0%A4%B8%E0%A4%AE%E0%A5%82%E0%A4%B9" title="फिनाइल समूह – Hindi" lang="hi" hreflang="hi" data-title="फिनाइल समूह" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Fenil" title="Fenil – Croatian" lang="hr" hreflang="hr" data-title="Fenil" 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/Gugus_fenil" title="Gugus fenil – Indonesian" lang="id" hreflang="id" data-title="Gugus fenil" 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-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%A0%D7%99%D7%9C" title="פניל – Hebrew" lang="he" hreflang="he" data-title="פניל" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Fenilcsoport" title="Fenilcsoport – Hungarian" lang="hu" hreflang="hu" data-title="Fenilcsoport" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Fenylgroep" title="Fenylgroep – Dutch" lang="nl" hreflang="nl" data-title="Fenylgroep" 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%83%95%E3%82%A7%E3%83%8B%E3%83%AB%E5%9F%BA" title="フェニル基 – Japanese" lang="ja" hreflang="ja" data-title="フェニル基" 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/Fenylgruppen" title="Fenylgruppen – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Fenylgruppen" 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/Fenil" title="Fenil – Uzbek" lang="uz" hreflang="uz" data-title="Fenil" 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-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%AB%E0%A8%BC%E0%A8%BF%E0%A8%A8%E0%A8%BE%E0%A8%88%E0%A8%B2_%E0%A8%B8%E0%A8%AE%E0%A9%82%E0%A8%B9" title="ਫ਼ਿਨਾਈਲ ਸਮੂਹ – Punjabi" lang="pa" hreflang="pa" data-title="ਫ਼ਿਨਾਈਲ ਸਮੂਹ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Grupa_fenylowa" title="Grupa fenylowa – Polish" lang="pl" hreflang="pl" data-title="Grupa fenylowa" 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/Fenil" title="Fenil – Portuguese" lang="pt" hreflang="pt" data-title="Fenil" 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/Fenil" title="Fenil – Romanian" lang="ro" hreflang="ro" data-title="Fenil" 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%A4%D0%B5%D0%BD%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="Фенильная группа – Russian" lang="ru" hreflang="ru" data-title="Фенильная 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/Fenylov%C3%A1_skupina" title="Fenylová skupina – Slovak" lang="sk" hreflang="sk" data-title="Fenylová skupina" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Fenylgrupp" title="Fenylgrupp – Swedish" lang="sv" hreflang="sv" data-title="Fenylgrupp" 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%AA%E0%AF%80%E0%AE%A9%E0%AF%88%E0%AE%B2%E0%AF%8D_%E0%AE%95%E0%AF%82%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AE%AE%E0%AF%8D" title="பீனைல் கூட்டம் – Tamil" lang="ta" hreflang="ta" data-title="பீனைல் கூட்டம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Fenil" title="Fenil – Turkish" lang="tr" hreflang="tr" data-title="Fenil" 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%A4%D0%B5%D0%BD%D1%96%D0%BB" title="Феніл – Ukrainian" lang="uk" hreflang="uk" data-title="Феніл" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Nh%C3%B3m_phenyl" title="Nhóm phenyl – Vietnamese" lang="vi" hreflang="vi" data-title="Nhóm phenyl" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%8B%AF%E5%9F%BA" title="苯基 – Wu" lang="wuu" hreflang="wuu" data-title="苯基" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%8B%AF%E5%9F%BA" title="苯基 – Cantonese" lang="yue" hreflang="yue" data-title="苯基" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a 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</div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Cyclic chemical group (–C₆H₅)</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Phenyl_group.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Phenyl_group.svg/140px-Phenyl_group.svg.png" decoding="async" width="140" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Phenyl_group.svg/210px-Phenyl_group.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Phenyl_group.svg/280px-Phenyl_group.svg.png 2x" data-file-width="146" data-file-height="125" /></a><figcaption>Phenyl radical group</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, the <b>phenyl group</b>, or <b>phenyl ring</b>, is a <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic</a> group of atoms with the formula <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>, and is often represented by the symbol <b>Ph</b> (archaically <b>φ</b>) or <b>Ø</b>. The phenyl group is closely related to <a href="/wiki/Benzene" title="Benzene">benzene</a> and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a <a href="/wiki/Functional_group" title="Functional group">functional group</a>. A phenyl group has six carbon atoms bonded together in a <a href="/wiki/Hexagonal" class="mw-redirect" title="Hexagonal">hexagonal</a> planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a <a href="/wiki/Substituent" title="Substituent">substituent</a>. Phenyl groups are commonplace in <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>.<sup id="cite_ref-March_1-0" class="reference"><a href="#cite_note-March-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Although often depicted with alternating double and single bonds, the phenyl group is <a href="/wiki/Aromaticity" title="Aromaticity">chemically aromatic</a> and has equal bond lengths between carbon atoms in the ring.<sup id="cite_ref-March_1-1" class="reference"><a href="#cite_note-March-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MSU_2-0" class="reference"><a href="#cite_note-MSU-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </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=Phenyl_group&action=edit&section=1" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Usually, a "phenyl group" is synonymous with <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> and is <a href="/wiki/Skeletal_formula#Pseudoelement_symbols" title="Skeletal formula">represented by the symbol</a> Ph (archaically, <a href="/wiki/%CE%A6" class="mw-redirect" title="Φ">Φ</a>), or Ø. Benzene is sometimes denoted as PhH. Phenyl groups are generally attached to other atoms or groups. For example, <a href="/wiki/Triphenylmethane" title="Triphenylmethane">triphenylmethane</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ph<sub class="template-chem2-sub">3</sub>CH</span>) has three phenyl groups attached to the same carbon center. Many or even most phenyl compounds are not described with the term "phenyl". For example, the chloro derivative <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>Cl</span> is normally called <a href="/wiki/Chlorobenzene" title="Chlorobenzene">chlorobenzene</a>, although it could be called phenyl chloride. In special (and rare) cases, isolated phenyl groups are detected: the phenyl anion (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<span class="template-chem2-su"><span>−</span><span>5</span></span></span>), the phenyl cation (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<span class="template-chem2-su"><span>+</span><span>5</span></span></span>), and the phenyl <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a> (<span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">•</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span></span>). </p><p>Although Ph and phenyl uniquely denote <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>, substituted derivatives also are described using the phenyl terminology. For example, <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">4</sub>NO<sub class="template-chem2-sub">2</sub>−</span> is nitrophenyl, and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>F<sub class="template-chem2-sub">5</sub>−</span> is pentafluorophenyl. Monosubstituted phenyl groups (that is, disubstituted benzenes) are associated with <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">electrophilic aromatic substitution</a> reactions and the products follow the <a href="/wiki/Arene_substitution_pattern" title="Arene substitution pattern">arene substitution pattern</a>. So, a given substituted phenyl compound has three isomers, <i>ortho</i> (1,2-disubstitution), <i>meta</i> (1,3-disubstitution) and <i>para</i> (1,4-disubstitution). A disubstituted phenyl compound (trisubstituted benzene) may be, for example, 1,3,5-trisubstituted or 1,2,3-trisubstituted. Higher degrees of substitution, of which the pentafluorophenyl group is an example, exist and are named according to IUPAC nomenclature. </p> <div class="mw-heading mw-heading3"><h3 id="Etymology">Etymology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenyl_group&action=edit&section=2" title="Edit section: Etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenyl is derived from <a href="/wiki/French_language" title="French language">French</a> <i> phényle</i>, which in turn derived from <a href="/wiki/Greek_language" title="Greek language">Greek</a> <i> </i>φαίνω<i> (phaino)</i> 'shining', as the first phenyl compounds named were byproducts of <a href="/wiki/History_of_manufactured_gas" class="mw-redirect" title="History of manufactured gas">making and refining</a> various <a href="/wiki/Gas_lighting" title="Gas lighting">gases used for lighting</a>.<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> According to McMurry, "The word is derived from <a href="/wiki/Greek_language" title="Greek language">Greek</a> <i> pheno</i> 'I bear light', commemorating the discovery of benzene by <a href="/wiki/Michael_Faraday" title="Michael Faraday">Michael Faraday</a> in 1825 from the oily residue left by the illuminating gas used in London street lamps."<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="Structure,_bonding,_and_characterization"><span id="Structure.2C_bonding.2C_and_characterization"></span>Structure, bonding, and characterization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenyl_group&action=edit&section=3" title="Edit section: Structure, bonding, and characterization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenyl compounds are derived from <a href="/wiki/Benzene" title="Benzene">benzene</a> (<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">6</sub></span>), at least conceptually and often in terms of their production. In terms of its electronic properties, the phenyl group is related to a <a href="/wiki/Vinyl_group" title="Vinyl group">vinyl group</a>. It is generally considered an inductively withdrawing group (-<i>I</i>), because of the higher electronegativity of sp<sup>2</sup> carbon atoms, and a resonance donating group (+<i>M</i>), due to the ability of its π system to donate electron density when conjugation is possible.<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> The phenyl group is <a href="/wiki/Hydrophobic" class="mw-redirect" title="Hydrophobic">hydrophobic</a>. Phenyl groups tend to resist oxidation and reduction. Phenyl groups (like all aromatic compounds) have enhanced stability in comparison to equivalent bonding in <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> (non-aromatic) groups. This increased stability is due to the unique properties of aromatic <a href="/wiki/Molecular_orbital_theory" title="Molecular orbital theory">molecular orbitals</a>.<sup id="cite_ref-MSU_2-1" class="reference"><a href="#cite_note-MSU-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>The bond lengths between carbon atoms in a phenyl group are approximately 1.4 <a href="/wiki/%C3%85ngstr%C3%B6m" class="mw-redirect" title="Ångström">Å</a>.<sup id="cite_ref-Hameka1987_6-0" class="reference"><a href="#cite_note-Hameka1987-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>In <sup>1</sup>H-<a href="/wiki/Nuclear_magnetic_resonance" title="Nuclear magnetic resonance">NMR</a> spectroscopy, protons of a phenyl group typically have <a href="/wiki/Chemical_shift" title="Chemical shift">chemical shifts</a> around 7.27 ppm. These chemical shifts are influenced by <a href="/wiki/Aromatic_ring_current" title="Aromatic ring current">aromatic ring current</a> and may change depending on substituents. </p> <div class="mw-heading mw-heading2"><h2 id="Preparation,_occurrence,_and_applications"><span id="Preparation.2C_occurrence.2C_and_applications"></span>Preparation, occurrence, and applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenyl_group&action=edit&section=4" title="Edit section: Preparation, occurrence, and applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenyl groups are usually introduced using reagents that behave as sources of the phenyl anion or the phenyl cation. Representative reagents include <a href="/wiki/Phenyllithium" title="Phenyllithium">phenyllithium</a> (<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>Li</span>) and <a href="/wiki/Phenylmagnesium_bromide" title="Phenylmagnesium bromide">phenylmagnesium bromide</a> (<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>MgBr</span>). Electrophiles are attacked by benzene to give phenyl derivatives: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {C6H6 + E+ -> C6H5E + H+}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msup> <mtext>E</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>E</mtext> <mo>+</mo> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {C6H6 + E+ -> C6H5E + H+}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/f67d3c57a5ce2ed99b86a4d2c6b3a4eece4c8fbd" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:29.766ex; height:3.176ex;" alt="{\displaystyle {\ce {C6H6 + E+ -> C6H5E + H+}}}"></span></dd></dl> <p>where <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">E<sup class="template-chem2-sup">+</sup></span> (the "electrophile") = <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cl<sup class="template-chem2-sup">+</sup>, NO<span class="template-chem2-su"><span>+</span><span>2</span></span>, SO<sub class="template-chem2-sub">3</sub></span>. These reactions are called <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">electrophilic aromatic substitutions</a>. </p> <ul class="gallery mw-gallery-traditional" style="max-width: 1115px;"> <li class="gallerycaption">Representative compounds containing phenyl groups</li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Atorvastatin.svg" class="mw-file-description" title="Atorvastatin (Lipitor), a blockbuster drug featuring two phenyl and one p-fluorophenyl groups. It is used to lower cholesterol in people with hypercholesterolaemia."><img alt="Atorvastatin (Lipitor), a blockbuster drug featuring two phenyl and one p-fluorophenyl groups. It is used to lower cholesterol in people with hypercholesterolaemia." src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Atorvastatin.svg/180px-Atorvastatin.svg.png" decoding="async" width="180" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Atorvastatin.svg/270px-Atorvastatin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Atorvastatin.svg/360px-Atorvastatin.svg.png 2x" data-file-width="512" data-file-height="264" /></a></span></div> <div class="gallerytext"><a href="/wiki/Atorvastatin" title="Atorvastatin">Atorvastatin (Lipitor)</a>, a <a href="/wiki/Pharmaceutical_drug#Blockbuster_drug" class="mw-redirect" title="Pharmaceutical drug">blockbuster drug</a> featuring two phenyl and one <i>p</i>-fluorophenyl groups. It is used to lower cholesterol in people with <a href="/wiki/Hypercholesterolaemia" class="mw-redirect" title="Hypercholesterolaemia">hypercholesterolaemia</a>.</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Fexofenadine.svg" class="mw-file-description" title="Fexofenadine (Allegra, Telfast), another blockbuster drug, which features a diphenylmethyl group as well as a p-phenylene (C6H4) group. It is an antihistamine used to treat allergies."><img alt="Fexofenadine (Allegra, Telfast), another blockbuster drug, which features a diphenylmethyl group as well as a p-phenylene (C6H4) group. It is an antihistamine used to treat allergies." src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Fexofenadine.svg/180px-Fexofenadine.svg.png" decoding="async" width="180" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Fexofenadine.svg/270px-Fexofenadine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Fexofenadine.svg/360px-Fexofenadine.svg.png 2x" data-file-width="275" data-file-height="138" /></a></span></div> <div class="gallerytext"><a href="/wiki/Fexofenadine" title="Fexofenadine">Fexofenadine (Allegra, Telfast)</a>, another blockbuster drug, which features a diphenylmethyl group as well as a <i>p</i>-<a href="/wiki/Phenylene" class="mw-redirect" title="Phenylene">phenylene</a> (<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">4</sub></span>) group. It is an <a href="/wiki/Antihistamine" title="Antihistamine">antihistamine</a> used to treat <a href="/wiki/Allergies" class="mw-redirect" title="Allergies">allergies</a>.</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Phenylalanin_-_Phenylalanine.svg" class="mw-file-description" title="Phenylalanine, a common amino acid."><img alt="Phenylalanine, a common amino acid." src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Phenylalanin_-_Phenylalanine.svg/180px-Phenylalanin_-_Phenylalanine.svg.png" decoding="async" width="180" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Phenylalanin_-_Phenylalanine.svg/270px-Phenylalanin_-_Phenylalanine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Phenylalanin_-_Phenylalanine.svg/360px-Phenylalanin_-_Phenylalanine.svg.png 2x" data-file-width="232" data-file-height="128" /></a></span></div> <div class="gallerytext"><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a>, a common amino acid.</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Bifenyl.svg" class="mw-file-description" title="Biphenyl, consisting of two phenyl groups. The two rings tend not to be coplanar."><img alt="Biphenyl, consisting of two phenyl groups. The two rings tend not to be coplanar." src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Bifenyl.svg/180px-Bifenyl.svg.png" decoding="async" width="180" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Bifenyl.svg/270px-Bifenyl.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Bifenyl.svg/360px-Bifenyl.svg.png 2x" data-file-width="1032" data-file-height="369" /></a></span></div> <div class="gallerytext"><a href="/wiki/Biphenyl" title="Biphenyl">Biphenyl</a>, consisting of two phenyl groups. The two rings tend not to be coplanar.</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Chlorobenzene2.svg" class="mw-file-description" title="Chlorobenzene (or phenyl chloride), a solvent."><img alt="Chlorobenzene (or phenyl chloride), a solvent." src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Chlorobenzene2.svg/72px-Chlorobenzene2.svg.png" decoding="async" width="72" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Chlorobenzene2.svg/108px-Chlorobenzene2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/Chlorobenzene2.svg/144px-Chlorobenzene2.svg.png 2x" data-file-width="512" data-file-height="853" /></a></span></div> <div class="gallerytext"><a href="/wiki/Chlorobenzene" title="Chlorobenzene">Chlorobenzene</a> (or phenyl chloride), a solvent.</div> </li> </ul> <p>Phenyl groups are found in many organic compounds, both natural and synthetic (see figure). Most common among natural products is the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>, which contains a phenyl group. A major product of the <a href="/wiki/Petrochemical_industry" title="Petrochemical industry">petrochemical industry</a> is "<a href="/wiki/Benzene#Production" title="Benzene">BTX</a>" consisting of benzene, toluene, and xylene - all of which are building blocks for phenyl compounds. The <a href="/wiki/Polymer" title="Polymer">polymer</a> <a href="/wiki/Polystyrene" title="Polystyrene">polystyrene</a> is derived from a phenyl-containing monomer and owes its properties to the rigidity and hydrophobicity of the phenyl groups. Many drugs as well as many pollutants contain phenyl rings. One of the simplest phenyl-containing compounds is <a href="/wiki/Phenol" title="Phenol">phenol</a>, <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>OH</span>. It is often said the <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">resonance stability</a> of phenol makes it a stronger <a href="/wiki/Acid" title="Acid">acid</a> than that of <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> <a href="/wiki/Alcohols" class="mw-redirect" title="Alcohols">alcohols</a> such as <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> (<a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">p<i>K</i><sub>a</sub></a> = 10 vs. 16–18). However, a significant contribution is the greater <a href="/wiki/Electronegativity" title="Electronegativity">electronegativity</a> of the <i>sp</i><sup>2</sup> <a href="/wiki/Alpha_carbon" class="mw-redirect" title="Alpha carbon">alpha carbon</a> in phenol compared to the <i>sp</i><sup>3</sup> alpha carbon in aliphatic alcohols.<sup id="cite_ref-Silva2009_7-0" class="reference"><a href="#cite_note-Silva2009-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <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=Phenyl_group&action=edit&section=5" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-March-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-March_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-March_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMarch1992" class="citation book cs1">March, Jerry (1992). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/advancedorganicc04edmarc"><i>Advanced organic chemistry: reactions, mechanisms, and structure</i></a></span> (4th ed.). New York: Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-60180-7" title="Special:BookSources/978-0-471-60180-7"><bdi>978-0-471-60180-7</bdi></a>.</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%3A+reactions%2C+mechanisms%2C+and+structure&rft.place=New+York&rft.edition=4th&rft.pub=Wiley&rft.date=1992&rft.isbn=978-0-471-60180-7&rft.aulast=March&rft.aufirst=Jerry&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fadvancedorganicc04edmarc&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenyl+group" class="Z3988"></span></span> </li> <li id="cite_note-MSU-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-MSU_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MSU_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/react3.htm">"Aromaticity. Benzene and Other Aromatic Compounds"</a>. <i>Virtual Textbook of Organic Chemistry</i>. Michigan State University.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Virtual+Textbook+of+Organic+Chemistry&rft.atitle=Aromaticity.+Benzene+and+Other+Aromatic+Compounds&rft_id=http%3A%2F%2Fwww2.chemistry.msu.edu%2Ffaculty%2Freusch%2FVirtTxtJml%2Freact3.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenyl+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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20130216194714/http://oxforddictionaries.com/us/definition/american_english/phenyl">"phenyl"</a>. <i>English by Lexico Dictionaries</i>. Archived from <a rel="nofollow" class="external text" href="http://www.oxforddictionaries.com/us/definition/american_english/phenyl">the original</a> on February 16, 2013<span class="reference-accessdate">. Retrieved <span class="nowrap">24 July</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=English+by+Lexico+Dictionaries&rft.atitle=phenyl&rft_id=http%3A%2F%2Fwww.oxforddictionaries.com%2Fus%2Fdefinition%2Famerican_english%2Fphenyl&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenyl+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="CITEREFMcMurry2009" class="citation book cs1">McMurry, John E. (2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Ffs7AAAAQBAJ"><i>Organic Chemistry, Enhanced Edition</i></a>. Cengage Learning. p. 518. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781111790042" title="Special:BookSources/9781111790042"><bdi>9781111790042</bdi></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%2C+Enhanced+Edition&rft.pages=518&rft.pub=Cengage+Learning&rft.date=2009&rft.isbn=9781111790042&rft.aulast=McMurry&rft.aufirst=John+E.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFfs7AAAAQBAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenyl+group" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHanschLeoTaft1991" class="citation journal cs1">Hansch, Corwin.; Leo, A.; Taft, R. W. (1991-03-01). "A survey of Hammett substituent constants and resonance and field parameters". <i>Chemical Reviews</i>. <b>91</b> (2): 165–195. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr00002a004">10.1021/cr00002a004</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0009-2665">0009-2665</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=A+survey+of+Hammett+substituent+constants+and+resonance+and+field+parameters&rft.volume=91&rft.issue=2&rft.pages=165-195&rft.date=1991-03-01&rft_id=info%3Adoi%2F10.1021%2Fcr00002a004&rft.issn=0009-2665&rft.aulast=Hansch&rft.aufirst=Corwin.&rft.au=Leo%2C+A.&rft.au=Taft%2C+R.+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenyl+group" class="Z3988"></span></span> </li> <li id="cite_note-Hameka1987-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-Hameka1987_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHameka1987" class="citation journal cs1">Hameka, Hendrik F. (1987). "Computation of the structures of the phenyl and benzyl radicals with the UHF method". <i>The Journal of Organic Chemistry</i>. <b>52</b> (22): 5025–5026. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00231a035">10.1021/jo00231a035</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Computation+of+the+structures+of+the+phenyl+and+benzyl+radicals+with+the+UHF+method&rft.volume=52&rft.issue=22&rft.pages=5025-5026&rft.date=1987&rft_id=info%3Adoi%2F10.1021%2Fjo00231a035&rft.issn=0022-3263&rft.aulast=Hameka&rft.aufirst=Hendrik+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenyl+group" class="Z3988"></span></span> </li> <li id="cite_note-Silva2009-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-Silva2009_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSilva2009" class="citation journal cs1">Silva, Pedro Jorge (2009). "Inductive and Resonance Effects on the Acidities of Phenol, Enols, and Carbonyl α-Hydrogens". <i>The Journal of Organic Chemistry</i>. <b>74</b> (2): 914–916. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo8018736">10.1021/jo8018736</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10284%2F3294">10284/3294</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</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/19053615">19053615</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Inductive+and+Resonance+Effects+on+the+Acidities+of+Phenol%2C+Enols%2C+and+Carbonyl+%CE%B1-Hydrogens&rft.volume=74&rft.issue=2&rft.pages=914-916&rft.date=2009&rft_id=info%3Ahdl%2F10284%2F3294&rft.issn=0022-3263&rft_id=info%3Apmid%2F19053615&rft_id=info%3Adoi%2F10.1021%2Fjo8018736&rft.aulast=Silva&rft.aufirst=Pedro+Jorge&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenyl+group" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenyl_group&action=edit&section=6" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span> Media related to <a href="https://commons.wikimedia.org/wiki/Category:Phenyl_group" class="extiw" title="commons:Category:Phenyl group">Phenyl group</a> at Wikimedia Commons</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline 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style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a class="mw-selflink selflink">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" 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