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vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Aromaticité"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Aromaticité</span> </div> </a> <ul id="toc-Aromaticité-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bibliographie" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Bibliographie"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Bibliographie</span> </div> </a> <ul id="toc-Bibliographie-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes_et_références" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes_et_références"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Notes et références</span> </div> </a> <ul id="toc-Notes_et_références-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Liens_externes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Liens_externes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Liens externes</span> </div> </a> <ul id="toc-Liens_externes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Voir_aussi" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Voir_aussi"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Voir aussi</span> </div> </a> <ul id="toc-Voir_aussi-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="Sommaire" 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="Basculer la table des matières" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Basculer la table des matières</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Pyrrole</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="Aller à un article dans une autre langue. Disponible en 43 langues." > <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-43" 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">43 langues</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/Pirrool" title="Pirrool – afrikaans" lang="af" hreflang="af" data-title="Pirrool" 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%A8%D9%8A%D8%B1%D9%88%D9%84" title="بيرول – arabe" lang="ar" hreflang="ar" data-title="بيرول" data-language-autonym="العربية" data-language-local-name="arabe" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Pirrol" title="Pirrol – azerbaïdjanais" lang="az" hreflang="az" data-title="Pirrol" data-language-autonym="Azərbaycanca" data-language-local-name="azerbaïdjanais" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%BE%DB%8C%D8%B1%D9%88%D9%84" title="پیرول – South Azerbaijani" lang="azb" hreflang="azb" data-title="پیرول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9F%D0%B8%D1%80%D0%BE%D0%BB" title="Пирол – bulgare" lang="bg" hreflang="bg" data-title="Пирол" data-language-autonym="Български" data-language-local-name="bulgare" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Pirol" title="Pirol – bosniaque" lang="bs" hreflang="bs" data-title="Pirol" data-language-autonym="Bosanski" data-language-local-name="bosniaque" 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/Pirrole" title="Pirrole – catalan" lang="ca" hreflang="ca" data-title="Pirrole" 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/Pyrrol" title="Pyrrol – tchèque" lang="cs" hreflang="cs" data-title="Pyrrol" data-language-autonym="Čeština" data-language-local-name="tchèque" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Pyrrol" title="Pyrrol – allemand" lang="de" hreflang="de" data-title="Pyrrol" data-language-autonym="Deutsch" data-language-local-name="allemand" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CF%85%CF%81%CF%81%CF%8C%CE%BB%CE%B9%CE%BF" title="Πυρρόλιο – grec" lang="el" hreflang="el" data-title="Πυρρόλιο" data-language-autonym="Ελληνικά" data-language-local-name="grec" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Pyrrole" title="Pyrrole – anglais" lang="en" hreflang="en" data-title="Pyrrole" data-language-autonym="English" data-language-local-name="anglais" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Pirolo_(kemio)" title="Pirolo (kemio) – espéranto" lang="eo" hreflang="eo" data-title="Pirolo (kemio)" data-language-autonym="Esperanto" data-language-local-name="espéranto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Pirrol" title="Pirrol – espagnol" lang="es" hreflang="es" data-title="Pirrol" data-language-autonym="Español" data-language-local-name="espagnol" 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/Pirrol" title="Pirrol – basque" lang="eu" hreflang="eu" data-title="Pirrol" 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/%D9%BE%DB%8C%D8%B1%D9%88%D9%84" title="پیرول – persan" lang="fa" hreflang="fa" data-title="پیرول" data-language-autonym="فارسی" data-language-local-name="persan" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Pyrroli" title="Pyrroli – finnois" lang="fi" hreflang="fi" data-title="Pyrroli" data-language-autonym="Suomi" data-language-local-name="finnois" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Pirrol" title="Pirrol – galicien" lang="gl" hreflang="gl" data-title="Pirrol" data-language-autonym="Galego" data-language-local-name="galicien" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%99%D7%A8%D7%95%D7%9C" title="פירול – hébreu" lang="he" hreflang="he" data-title="פירול" data-language-autonym="עברית" data-language-local-name="hébreu" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AA%E0%A4%BE%E0%A4%87%E0%A4%B0%E0%A5%8B%E0%A4%B2" title="पाइरोल – hindi" lang="hi" hreflang="hi" data-title="पाइरोल" 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/Pirol" title="Pirol – croate" lang="hr" hreflang="hr" data-title="Pirol" data-language-autonym="Hrvatski" data-language-local-name="croate" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Pirrol" title="Pirrol – hongrois" lang="hu" hreflang="hu" data-title="Pirrol" data-language-autonym="Magyar" data-language-local-name="hongrois" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8A%D5%AB%D6%80%D5%B8%D5%AC" title="Պիրոլ – arménien" lang="hy" hreflang="hy" data-title="Պիրոլ" data-language-autonym="Հայերեն" data-language-local-name="arménien" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Pirola" title="Pirola – indonésien" lang="id" hreflang="id" data-title="Pirola" data-language-autonym="Bahasa Indonesia" data-language-local-name="indonésien" 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/Pirrolo" title="Pirrolo – italien" lang="it" hreflang="it" data-title="Pirrolo" data-language-autonym="Italiano" data-language-local-name="italien" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%94%E3%83%AD%E3%83%BC%E3%83%AB" title="ピロール – japonais" lang="ja" hreflang="ja" data-title="ピロール" data-language-autonym="日本語" data-language-local-name="japonais" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%94%BC%EB%A1%A4" title="피롤 – coréen" lang="ko" hreflang="ko" data-title="피롤" data-language-autonym="한국어" data-language-local-name="coréen" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Pirol" title="Pirol – lombard" lang="lmo" hreflang="lmo" data-title="Pirol" data-language-autonym="Lombard" data-language-local-name="lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Pirols" title="Pirols – letton" lang="lv" hreflang="lv" data-title="Pirols" data-language-autonym="Latviešu" data-language-local-name="letton" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Pyrrool" title="Pyrrool – néerlandais" lang="nl" hreflang="nl" data-title="Pyrrool" data-language-autonym="Nederlands" data-language-local-name="néerlandais" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Pyrrol" title="Pyrrol – norvégien bokmål" lang="nb" hreflang="nb" data-title="Pyrrol" data-language-autonym="Norsk bokmål" data-language-local-name="norvégien 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/Pirol" title="Pirol – polonais" lang="pl" hreflang="pl" data-title="Pirol" data-language-autonym="Polski" data-language-local-name="polonais" 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/Pirrol" title="Pirrol – portugais" lang="pt" hreflang="pt" data-title="Pirrol" data-language-autonym="Português" data-language-local-name="portugais" 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/Pirol" title="Pirol – roumain" lang="ro" hreflang="ro" data-title="Pirol" data-language-autonym="Română" data-language-local-name="roumain" 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%9F%D0%B8%D1%80%D1%80%D0%BE%D0%BB" title="Пиррол – russe" lang="ru" hreflang="ru" data-title="Пиррол" data-language-autonym="Русский" data-language-local-name="russe" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Pirol" title="Pirol – serbo-croate" lang="sh" hreflang="sh" data-title="Pirol" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="serbo-croate" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Pyrol" title="Pyrol – slovaque" lang="sk" hreflang="sk" data-title="Pyrol" data-language-autonym="Slovenčina" data-language-local-name="slovaque" 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/Pirol" title="Pirol – serbe" lang="sr" hreflang="sr" data-title="Pirol" data-language-autonym="Српски / srpski" data-language-local-name="serbe" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Pyrrol" title="Pyrrol – suédois" lang="sv" hreflang="sv" data-title="Pyrrol" data-language-autonym="Svenska" data-language-local-name="suédois" 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%AE%BF%E0%AE%B0%E0%AF%8D%E0%AE%B0%E0%AF%8B%E0%AE%B2%E0%AF%8D" title="பிர்ரோல் – tamoul" lang="ta" hreflang="ta" data-title="பிர்ரோல்" data-language-autonym="தமிழ்" data-language-local-name="tamoul" 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/Pirol" title="Pirol – turc" lang="tr" hreflang="tr" data-title="Pirol" data-language-autonym="Türkçe" data-language-local-name="turc" 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%9F%D1%96%D1%80%D0%BE%D0%BB" title="Пірол – ukrainien" lang="uk" hreflang="uk" data-title="Пірол" data-language-autonym="Українська" data-language-local-name="ukrainien" 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/Pyrol" title="Pyrol – vietnamien" lang="vi" hreflang="vi" data-title="Pyrol" data-language-autonym="Tiếng Việt" data-language-local-name="vietnamien" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%90%A1%E5%92%AF" title="吡咯 – chinois" lang="zh" hreflang="zh" data-title="吡咯" data-language-autonym="中文" data-language-local-name="chinois" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q242627#sitelinks-wikipedia" title="Modifier les liens interlangues" class="wbc-editpage">Modifier les liens</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Espaces de noms"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> 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code</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Pyrrole&action=history" title="Historique des versions de cette page [h]" accesskey="h"><span>Voir l’historique</span></a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Outils de la page"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " aria-label="Outils" > <label id="vector-page-tools-dropdown-label" for="vector-page-tools-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">Outils</span> </label> <div class="vector-dropdown-content"> <div 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title="Plus d’options" > <div class="vector-menu-heading"> Actions </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected vector-more-collapsible-item mw-list-item"><a href="/wiki/Pyrrole"><span>Lire</span></a></li><li id="ca-more-ve-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Pyrrole&veaction=edit" title="Modifier cette page [v]" accesskey="v"><span>Modifier</span></a></li><li id="ca-more-edit" class="collapsible vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Pyrrole&action=edit" title="Modifier le wikicode de cette page [e]" accesskey="e"><span>Modifier le code</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Pyrrole&action=history"><span>Voir l’historique</span></a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> Général </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Sp%C3%A9cial:Pages_li%C3%A9es/Pyrrole" title="Liste des pages liées qui pointent sur celle-ci [j]" accesskey="j"><span>Pages liées</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Sp%C3%A9cial:Suivi_des_liens/Pyrrole" rel="nofollow" title="Liste des modifications récentes des pages appelées par celle-ci [k]" accesskey="k"><span>Suivi des pages liées</span></a></li><li id="t-upload" class="mw-list-item"><a href="/wiki/Aide:Importer_un_fichier" title="Téléverser des fichiers [u]" accesskey="u"><span>Téléverser un fichier</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Sp%C3%A9cial:Pages_sp%C3%A9ciales" title="Liste de toutes les pages spéciales [q]" accesskey="q"><span>Pages spéciales</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Pyrrole&oldid=202547269" title="Adresse permanente de cette version de cette page"><span>Lien permanent</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Pyrrole&action=info" title="Davantage d’informations sur cette page"><span>Informations sur la page</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Sp%C3%A9cial:Citer&page=Pyrrole&id=202547269&wpFormIdentifier=titleform" title="Informations sur la manière de citer cette page"><span>Citer cette page</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Sp%C3%A9cial:UrlShortener&url=https%3A%2F%2Ffr.wikipedia.org%2Fwiki%2FPyrrole"><span>Obtenir l'URL raccourcie</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Sp%C3%A9cial:QrCode&url=https%3A%2F%2Ffr.wikipedia.org%2Fwiki%2FPyrrole"><span>Télécharger le code QR</span></a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> Imprimer / exporter </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="coll-create_a_book" class="mw-list-item"><a href="/w/index.php?title=Sp%C3%A9cial:Livre&bookcmd=book_creator&referer=Pyrrole"><span>Créer un livre</span></a></li><li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Sp%C3%A9cial:DownloadAsPdf&page=Pyrrole&action=show-download-screen"><span>Télécharger comme PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Pyrrole&printable=yes" title="Version imprimable de cette page [p]" accesskey="p"><span>Version imprimable</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> Dans d’autres projets </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="wb-otherproject-link wb-otherproject-commons mw-list-item"><a href="https://commons.wikimedia.org/wiki/Category:Pyrrole" hreflang="en"><span>Wikimedia Commons</span></a></li><li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q242627" title="Lien vers l’élément dans le dépôt de données connecté [g]" accesskey="g"><span>Élément Wikidata</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Outils de la page"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Apparence"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Apparence</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">déplacer vers la barre latérale</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">masquer</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">Un article de Wikipédia, l'encyclopédie libre.</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="fr" dir="ltr"><div class="bandeau-container metadata homonymie hatnote"><div class="bandeau-cell bandeau-icone" style="display:table-cell;padding-right:0.5em"><span class="noviewer" typeof="mw:File"><a href="/wiki/Aide:Homonymie" title="Aide:Homonymie"><img alt="Page d’aide sur l’homonymie" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/Confusion_colour.svg/20px-Confusion_colour.svg.png" decoding="async" width="20" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/Confusion_colour.svg/30px-Confusion_colour.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/Confusion_colour.svg/40px-Confusion_colour.svg.png 2x" data-file-width="260" data-file-height="200" /></a></span></div><div class="bandeau-cell" style="display:table-cell;padding-right:0.5em"> <p>Ne doit pas être confondu avec <a href="/wiki/Pyrole" title="Pyrole">Pyrole</a>. </p> </div></div> <div class="bandeau-container metadata homonymie hatnote"><div class="bandeau-cell bandeau-icone" style="display:table-cell;padding-right:0.5em"><span class="noviewer" typeof="mw:File"><a href="/wiki/Aide:Homonymie" title="Aide:Homonymie"><img alt="Page d’aide sur l’homonymie" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Logo_disambig.svg/20px-Logo_disambig.svg.png" decoding="async" width="20" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Logo_disambig.svg/30px-Logo_disambig.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Logo_disambig.svg/40px-Logo_disambig.svg.png 2x" data-file-width="512" data-file-height="375" /></a></span></div><div class="bandeau-cell" style="display:table-cell;padding-right:0.5em"> <p>Cet article concerne la molécule d'azole/pyrrole. Pour la famille de composés dérivés, voir <a href="/wiki/Azole" title="Azole">Azole</a>. </p> </div></div> <p class="mw-empty-elt"> </p> <table class="infobox_v2 infobox infobox--frwiki noarchive"> <tbody><tr> <td colspan="2" class="entete defaut" style="background-color:#FFDEAD;color:black;">Pyrrole </td></tr> <tr><td colspan="2" style="text-align:center; line-height: 1.5em;"><span typeof="mw:File/Frameless"><a href="/wiki/Fichier:Pyrrole.png" class="mw-file-description"><img alt="Image illustrative de l’article Pyrrole" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Pyrrole.png/280px-Pyrrole.png" decoding="async" width="280" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Pyrrole.png/420px-Pyrrole.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/15/Pyrrole.png/560px-Pyrrole.png 2x" data-file-width="1668" data-file-height="560" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center;">représentations du pyrrole</td> </tr><tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#FFDEAD; color:#000000">Identification</th></tr> <tr> <th scope="row"><a href="/wiki/Nomenclature_de_l%27UICPA" title="Nomenclature de l'UICPA">Nom UICPA</a> </th> <td><small>Azole</small> </td> </tr> <tr> <th scope="row"><a href="/wiki/Synonymie" title="Synonymie">Synonymes</a> </th> <td> <p>pyrrole </p> </td> </tr> <tr> <th scope="row"><a href="/wiki/Num%C3%A9ro_CAS" title="Numéro CAS">N<sup>o</sup> CAS</a> </th> <td><span class="reflink plainlinksneverexpand"><span class="noarchive"><a class="external text" href="//tools.wmflabs.org/magnustools/cas.php?cas=109-97-7&language=fr&title=Pyrrole">109-97-7</a></span></span> </td> </tr> <tr> <th scope="row"> N<sup>o</sup> <a href="/wiki/Agence_europ%C3%A9enne_des_produits_chimiques" title="Agence européenne des produits chimiques">ECHA</a> </th> <td><span class="plainlinks"><span class="noarchive"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.003.387">100.003.387</a></span></span></td> </tr> <tr> <th scope="row"><a href="/wiki/Num%C3%A9ro_CE" title="Numéro CE">N<sup>o</sup> CE</a> </th> <td>203-724-7 </td> </tr> <tr> <th scope="row"><a href="/wiki/PubChem" title="PubChem">PubChem</a> </th> <td><span class="reflink plainlinksneverexpand"><a rel="nofollow" class="external text" href="http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8027">8027</a></span> </td> </tr> <tr> <th scope="row"><a href="/wiki/GRAS" class="mw-redirect" title="GRAS"><span title="Flavor and Extract Manufacturers Association">FEMA</span></a> </th> <td><span class="plainlinks"><span class="noarchive"><a rel="nofollow" class="external text" href="http://www.fao.org/ag/agn/jecfa-flav/results.html?flavName=&groupName=-1&searchBy=fema&jecfa=&fema=3386&cas1=&cas2=&cas3="><span title="pyrrole">3386</span></a></span></span> </td> </tr> <tr> <th scope="row"><a href="/wiki/Simplified_Molecular_Input_Line_Entry_System" title="Simplified Molecular Input Line Entry System">SMILES</a> </th> <td><div class="NavFrame" title="[Afficher]/[Masquer]" style="border: none; padding: 0;"><div class="NavContent" style="display: none; text-align: left;">C1=CNC=C1 <br /><span class="reflink plainlinksneverexpand"><a rel="nofollow" class="external text" href="http://pubchem.ncbi.nlm.nih.gov/search/?smarts=C1%3DCNC%3DC1">PubChem</a></span>, <span class="reflink plainlinksneverexpand"><a rel="nofollow" class="external text" href="http://chemapps.stolaf.edu/jmol/jmol.php?title=Pyrrole&model=C1%3DCNC%3DC1">vue 3D</a></span></div></div> </td> </tr> <tr> <th scope="row"><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a> </th> <td><div class="NavFrame" title="[Afficher]/[Masquer]" style="border: none; padding: 0;"><div class="NavContent" style="display: none; text-align: left;"><b>InChI :</b> <span class="reflink plainlinksneverexpand"><a rel="nofollow" class="external text" href="http://chemapps.stolaf.edu/jmol/jmol.php?title=Pyrrole&model=InChI%3DInChI%3D1%2FC4H5N%2Fc1-2-4-5-3-1%2Fh1-5H">vue 3D</a></span> <br />InChI=InChI=1/C4H5N/c1-2-4-5-3-1/h1-5H <br /></div></div> </td> </tr> <tr> <th scope="row">Apparence </th> <td>liquide incolore </td> </tr> <tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#FFDEAD; color:#000000">Propriétés chimiques</th></tr> <tr> <th scope="row"><a href="/wiki/Formule_chimique" title="Formule chimique">Formule</a> </th> <td><a href="/wiki/Carbone" title="Carbone">C</a><sub>4</sub><a href="/wiki/Hydrog%C3%A8ne" title="Hydrogène">H</a><sub>5</sub><a href="/wiki/Azote" title="Azote">N</a>  <span class="page_h"><a href="/wiki/C4H5N" class="mw-redirect" title="C4H5N"><small>[Isomères]</small></a></span><br /> </td> </tr> <tr> <th scope="row"><a href="/wiki/Masse_molaire" title="Masse molaire">Masse molaire</a><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite_crochet">[</span>3<span class="cite_crochet">]</span></a></sup> </th> <td>67,089 2 ± 0,003 8 <a href="/wiki/Gramme" title="Gramme">g</a>/<a href="/wiki/Mole_(unit%C3%A9)" title="Mole (unité)">mol</a> <br /><small>C 71,61 %,  H 7,51 %,  N 20,88 %,  </small> </td> </tr> <tr> <th scope="row"><a href="/wiki/Constante_d%27acidit%C3%A9" title="Constante d'acidité">p<i>K</i><sub>a</sub></a> </th> <td>0,4 (PyrH+/PyrH)<br />16,5 (PyrH/Pyr-) </td> </tr> <tr> <th scope="row"><a href="/wiki/Dip%C3%B4le_%C3%A9lectrostatique#Moment_dipolaire" title="Dipôle électrostatique">Moment dipolaire</a> </th> <td><span class="nowrap"><span title="5,894 077 647E−30 C⋅m">1,767</span> ± 0,001 <span title="Debye">D</span></span><sup id="cite_ref-HandbookChemPhys89ed_1-0" class="reference"><a href="#cite_note-HandbookChemPhys89ed-1"><span class="cite_crochet">[</span>1<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <th scope="row">Diamètre moléculaire </th> <td><span class="nowrap"><span title="5,01 Å">0,501</span> <span title="nanomètre">nm</span></span><sup id="cite_ref-Yitzhak_Marcus_2-0" class="reference"><a href="#cite_note-Yitzhak_Marcus-2"><span class="cite_crochet">[</span>2<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#f7efa8; color:#000000">Propriétés physiques</th></tr> <tr> <th scope="row"><a href="/wiki/Point_de_fusion" title="Point de fusion"><abbr class="abbr" title="Température">T°</abbr> fusion</a> </th> <td><span title="−10,1 °F ou 249,8 K">−23,4 </span><abbr class="abbr" title="degré Celsius">°C</abbr><sup id="cite_ref-HSDB_4-0" class="reference"><a href="#cite_note-HSDB-4"><span class="cite_crochet">[</span>4<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <th scope="row"><a href="/wiki/Point_d%27%C3%A9bullition" title="Point d'ébullition"><abbr class="abbr" title="Température">T°</abbr> ébullition</a> </th> <td><span title="265,5 °F ou 402,9 K">129,7 </span><abbr class="abbr" title="degré Celsius">°C</abbr><sup id="cite_ref-HSDB_4-1" class="reference"><a href="#cite_note-HSDB-4"><span class="cite_crochet">[</span>4<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <th scope="row"><a href="/wiki/Solubilit%C3%A9" title="Solubilité">Solubilité</a> </th> <td><span class="nowrap"><span title="">45</span> <span title="Gramme">g</span>·<span title="Litre">l</span><sup>-1</sup></span> (eau, <span title="77 °F ou 298,2 K">25 </span><abbr class="abbr" title="degré Celsius">°C</abbr>);<br /> <p>Sol. dans l'<a href="/wiki/%C3%89thanol" title="Éthanol">alcool</a>, l'<a href="/wiki/%C3%89ther_di%C3%A9thylique" title="Éther diéthylique">éther</a> et les acides dilués<sup id="cite_ref-HSDB_4-2" class="reference"><a href="#cite_note-HSDB-4"><span class="cite_crochet">[</span>4<span class="cite_crochet">]</span></a></sup>. </p> </td> </tr> <tr> <th scope="row"><a href="/wiki/Polym%C3%A8re_en_solution#Approche_de_Hildebrand,_paramètre_de_solubilité" title="Polymère en solution">Paramètre de solubilité δ</a> </th> <td><span class="nowrap"><span title="12,12 cal1/2·cm-3/2">24,8</span> <span title="joule">J</span><sup>1/2</sup>·<span title="centimètre">cm</span><sup>-3/2</sup></span> (<span title="77 °F ou 298,2 K">25 </span><abbr class="abbr" title="degré Celsius">°C</abbr>)<sup id="cite_ref-Yitzhak_Marcus_2-1" class="reference"><a href="#cite_note-Yitzhak_Marcus-2"><span class="cite_crochet">[</span>2<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <th scope="row"><a href="/wiki/Masse_volumique" title="Masse volumique">Masse volumique</a> </th> <td><span class="nowrap"><span title="969,8 kg⋅m⁻³ ou −4,52 °Baumé">0,969 8</span> <span title="Gramme">g</span>·<span title="centimètre">cm</span><sup>-3</sup></span> (<span title="68 °F ou 293,2 K">20 </span><abbr class="abbr" title="degré Celsius">°C</abbr>)<sup id="cite_ref-HSDB_4-3" class="reference"><a href="#cite_note-HSDB-4"><span class="cite_crochet">[</span>4<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <th scope="row"><a href="/wiki/Point_d%27auto-inflammation" title="Point d'auto-inflammation"><abbr class="abbr" title="Température">T°</abbr> d'auto-inflammation</a> </th> <td><span title="1 022 °F ou 823,2 K">550 </span><abbr class="abbr" title="degré Celsius">°C</abbr> </td> </tr> <tr> <th scope="row"><a href="/wiki/Point_d%27%C3%A9clair" title="Point d'éclair">Point d’éclair</a> </th> <td><span title="102,2 °F ou 312,2 K">39 </span><abbr class="abbr" title="degré Celsius">°C</abbr> </td> </tr> <tr> <th scope="row"><a href="/wiki/Limite_d%27explosivit%C3%A9" title="Limite d'explosivité">Limites d’explosivité dans l’air</a> </th> <td><span class="nowrap"><span title="31 ml·l⁻¹ ou 31 000 ppmv">3,10</span>–<span title="148 ml·l⁻¹ ou 148 000 ppmv">14,8</span> <span title="pourcentage volumique">%vol</span></span> </td> </tr> <tr> <th scope="row"><a href="/wiki/Pression_de_vapeur_saturante" title="Pression de vapeur saturante">Pression de vapeur saturante</a> </th> <td><span class="nowrap"><span title="9 mbar ou 0,008 882 309 7 atm">9</span> <span title="hectopascal">hPa</span></span> (à <span title="68 °F ou 293,2 K">20 </span><abbr class="abbr" title="degré Celsius">°C</abbr>) </td> </tr> <tr> <th scope="row"><a href="/wiki/Point_critique_(thermodynamique)" title="Point critique (thermodynamique)">Point critique</a> </th> <td><span title="692,2 °F ou 639,9 K">366,75 </span><abbr class="abbr" title="degré Celsius">°C</abbr> <br /> 6,21·10⁶ Pa<sup id="cite_ref-HSDB_4-4" class="reference"><a href="#cite_note-HSDB-4"><span class="cite_crochet">[</span>4<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#FFDEAD; color:#000000">Thermochimie</th></tr> <tr> <th scope="row"><a href="/wiki/Capacit%C3%A9_thermique" title="Capacité thermique">C<sub>p</sub></a> </th> <td><div class="NavFrame" title="[+]/[-]" style="border:none; padding: 0;"><div class="NavContent" style="display:none; text-align:left;"><hr /> <p>équation<sup id="cite_ref-Yaws_5-0" class="reference"><a href="#cite_note-Yaws-5"><span class="cite_crochet">[</span>5<span class="cite_crochet">]</span></a></sup> : <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 C_{P}=(-7.680)+(3.1201E-1)\times T+(-1.1806E-4)\times T^{2}+(-2.7912E-8)\times T^{3}+(2.1314E-11)\times T^{4}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <msub> <mi>C</mi> <mrow class="MJX-TeXAtom-ORD"> <mi>P</mi> </mrow> </msub> <mo>=</mo> <mo stretchy="false">(</mo> <mo>−</mo> <mn>7.680</mn> <mo stretchy="false">)</mo> <mo>+</mo> <mo stretchy="false">(</mo> <mn>3.1201</mn> <mi>E</mi> <mo>−</mo> <mn>1</mn> <mo stretchy="false">)</mo> <mo>×</mo> <mi>T</mi> <mo>+</mo> <mo stretchy="false">(</mo> <mo>−</mo> <mn>1.1806</mn> <mi>E</mi> <mo>−</mo> <mn>4</mn> <mo stretchy="false">)</mo> <mo>×</mo> <msup> <mi>T</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msup> <mo>+</mo> <mo stretchy="false">(</mo> <mo>−</mo> <mn>2.7912</mn> <mi>E</mi> <mo>−</mo> <mn>8</mn> <mo stretchy="false">)</mo> <mo>×</mo> <msup> <mi>T</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> </msup> <mo>+</mo> <mo stretchy="false">(</mo> <mn>2.1314</mn> <mi>E</mi> <mo>−</mo> <mn>11</mn> <mo stretchy="false">)</mo> <mo>×</mo> <msup> <mi>T</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> </msup> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle C_{P}=(-7.680)+(3.1201E-1)\times T+(-1.1806E-4)\times T^{2}+(-2.7912E-8)\times T^{3}+(2.1314E-11)\times T^{4}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/3db0eec66ad6452193a413f47dadf312b752df25" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.838ex; width:108.789ex; height:3.176ex;" alt="{\displaystyle C_{P}=(-7.680)+(3.1201E-1)\times T+(-1.1806E-4)\times T^{2}+(-2.7912E-8)\times T^{3}+(2.1314E-11)\times T^{4}}"></span><br /> Capacité thermique du gaz en J·mol<sup>-1</sup>·K<sup>-1</sup> et température en kelvins, de 200 à 1 500 K.<br /> Valeurs calculées : <br />74,28 J·mol<sup>-1</sup>·K<sup>-1</sup> à 25 °C. </p> <table><tbody><tr><td> <table class="wikitable"> <tbody><tr><th>T<br />(K)</th> <th>T<br />(°C)</th> <th>C<sub>p</sub><br /><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 ({\tfrac {J}{kmol\times K}})}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mo stretchy="false">(</mo> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="false" scriptlevel="0"> <mfrac> <mi>J</mi> <mrow> <mi>k</mi> <mi>m</mi> <mi>o</mi> <mi>l</mi> <mo>×</mo> <mi>K</mi> </mrow> </mfrac> </mstyle> </mrow> <mo stretchy="false">)</mo> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle ({\tfrac {J}{kmol\times K}})}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/0284c56a605f091ad5194cf9ad3de996f5d757b2" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.338ex; width:8.972ex; height:3.843ex;" alt="{\displaystyle ({\tfrac {J}{kmol\times K}})}"></span></th> <th>C<sub>p</sub><br /><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 ({\tfrac {J}{kg\times K}})}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mo stretchy="false">(</mo> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="false" scriptlevel="0"> <mfrac> <mi>J</mi> <mrow> <mi>k</mi> <mi>g</mi> <mo>×</mo> <mi>K</mi> </mrow> </mfrac> </mstyle> </mrow> <mo stretchy="false">)</mo> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle ({\tfrac {J}{kg\times K}})}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/e2ffae996ebf9a4ddfe360b8b7aa9f0f89711fa4" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.671ex; width:7.03ex; height:4.176ex;" alt="{\displaystyle ({\tfrac {J}{kg\times K}})}"></span></th></tr> <tr><td>200</td> <td>−73,15</td> <td>49 810</td> <td>742</td></tr> <tr><td>286</td> <td>12,85</td> <td>71 388</td> <td>1 064</td></tr> <tr><td>330</td> <td>56,85</td> <td>81 676</td> <td>1 217</td></tr> <tr><td>373</td> <td>99,85</td> <td>91 238</td> <td>1 360</td></tr> <tr><td>416</td> <td>142,85</td> <td>100 314</td> <td>1 495</td></tr> <tr><td>460</td> <td>186,85</td> <td>109 101</td> <td>1 626</td></tr> <tr><td>503</td> <td>229,85</td> <td>117 203</td> <td>1 747</td></tr> <tr><td>546</td> <td>272,85</td> <td>124 833</td> <td>1 861</td></tr> <tr><td>590</td> <td>316,85</td> <td>132 159</td> <td>1 970</td></tr> <tr><td>633</td> <td>359,85</td> <td>138 859</td> <td>2 070</td></tr> <tr><td>676</td> <td>402,85</td> <td>145 117</td> <td>2 163</td></tr> <tr><td>720</td> <td>446,85</td> <td>151 075</td> <td>2 252</td></tr> <tr><td>763</td> <td>489,85</td> <td>156 478</td> <td>2 332</td></tr> <tr><td>806</td> <td>532,85</td> <td>161 484</td> <td>2 407</td></tr> <tr><td>850</td> <td>576,85</td> <td>166 215</td> <td>2 478</td></tr> </tbody></table> </td><td> <table class="wikitable"> <tbody><tr><th>T<br />(K)</th> <th>T<br />(°C)</th> <th>C<sub>p</sub><br /><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 ({\tfrac {J}{kmol\times K}})}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mo stretchy="false">(</mo> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="false" scriptlevel="0"> <mfrac> <mi>J</mi> <mrow> <mi>k</mi> <mi>m</mi> <mi>o</mi> <mi>l</mi> <mo>×</mo> <mi>K</mi> </mrow> </mfrac> </mstyle> </mrow> <mo stretchy="false">)</mo> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle ({\tfrac {J}{kmol\times K}})}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/0284c56a605f091ad5194cf9ad3de996f5d757b2" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.338ex; width:8.972ex; height:3.843ex;" alt="{\displaystyle ({\tfrac {J}{kmol\times K}})}"></span></th> <th>C<sub>p</sub><br /><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 ({\tfrac {J}{kg\times K}})}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mo stretchy="false">(</mo> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="false" scriptlevel="0"> <mfrac> <mi>J</mi> <mrow> <mi>k</mi> <mi>g</mi> <mo>×</mo> <mi>K</mi> </mrow> </mfrac> </mstyle> </mrow> <mo stretchy="false">)</mo> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle ({\tfrac {J}{kg\times K}})}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/e2ffae996ebf9a4ddfe360b8b7aa9f0f89711fa4" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.671ex; width:7.03ex; height:4.176ex;" alt="{\displaystyle ({\tfrac {J}{kg\times K}})}"></span></th></tr> <tr><td>893</td> <td>619,85</td> <td>170 475</td> <td>2 541</td></tr> <tr><td>936</td> <td>662,85</td> <td>174 400</td> <td>2 600</td></tr> <tr><td>980</td> <td>706,85</td> <td>178 094</td> <td>2 655</td></tr> <tr><td>1 023</td> <td>749,85</td> <td>181 414</td> <td>2 704</td></tr> <tr><td>1 066</td> <td>792,85</td> <td>184 476</td> <td>2 750</td></tr> <tr><td>1 110</td> <td>836,85</td> <td>187 372</td> <td>2 793</td></tr> <tr><td>1 153</td> <td>879,85</td> <td>190 003</td> <td>2 832</td></tr> <tr><td>1 196</td> <td>922,85</td> <td>192 468</td> <td>2 869</td></tr> <tr><td>1 240</td> <td>966,85</td> <td>194 857</td> <td>2 904</td></tr> <tr><td>1 283</td> <td>1 009,85</td> <td>197 096</td> <td>2 938</td></tr> <tr><td>1 326</td> <td>1 052,85</td> <td>199 280</td> <td>2 970</td></tr> <tr><td>1 370</td> <td>1 096,85</td> <td>201 499</td> <td>3 003</td></tr> <tr><td>1 413</td> <td>1 139,85</td> <td>203 695</td> <td>3 036</td></tr> <tr><td>1 456</td> <td>1 182,85</td> <td>205 961</td> <td>3 070</td></tr> <tr><td>1 500</td> <td>1 226,85</td> <td>208 399</td> <td>3 106</td></tr> </tbody></table> </td></tr></tbody></table> </div></div> </td> </tr> <tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#FFDEAD; color:#000000">Propriétés électroniques</th></tr> <tr> <th scope="row"><abbr class="abbr" title="Première">1<sup>re</sup></abbr> <a href="/wiki/%C3%89nergie_d%27ionisation" title="Énergie d'ionisation">énergie d'ionisation</a> </th> <td><span class="nowrap"><span title="1,314 906 2E−18 J ou 791,854 9 kJ·mol⁻¹ ou 151,1 nm">8,207</span> ± 0,005 <span title="Électron-volt">eV</span></span> (gaz)<sup id="cite_ref-ouvrage_6-0" class="reference"><a href="#cite_note-ouvrage-6"><span class="cite_crochet">[</span>6<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#FFDEAD; color:#000000">Propriétés optiques</th></tr> <tr> <th scope="row"><a href="/wiki/Indice_de_r%C3%A9fraction" title="Indice de réfraction">Indice de réfraction</a> </th> <td><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 {\textit {n}}_{D}^{20}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mtext class="MJX-tex-mathit" mathvariant="italic">n</mtext> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>D</mi> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>20</mn> </mrow> </msubsup> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\textit {n}}_{D}^{20}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/85a93dd4d320509299beabe9b112bcd3250df8b9" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:3.183ex; height:3.176ex;" alt="{\displaystyle {\textit {n}}_{D}^{20}}"></span> 1,5085<sup id="cite_ref-HSDB_4-5" class="reference"><a href="#cite_note-HSDB-4"><span class="cite_crochet">[</span>4<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#ffb4b4; color:#000000">Précautions</th></tr> <tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#eeeeee; color:#000000"><a href="/wiki/NFPA_704" title="NFPA 704">NFPA 704</a></th></tr> <tr> <td colspan="2" style="text-align:center;"><div class="center"><div style="position: relative; height: 85px; width: 75px;margin: 0 auto"> <div style="position: absolute; height: 75px; width: 75px;"> <p><span typeof="mw:File"><a href="/wiki/Fichier:NFPA_704.svg" class="mw-file-description" title="Symbole NFPA 704"><img alt="Symbole NFPA 704" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/75px-NFPA_704.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/113px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/150px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> </p> </div><div style="width: 75px; height: 2em; text-align: center; vertical-align: middle; position: absolute; top: 15px; font-size: large;"><a href="/wiki/NFPA_704#Inflammabilité2" title="NFPA 704"><span style="color: black;" title="Produit qui ne peut s'enflammer qu'après un chauffage modéré ou une exposition à une source de chaleur relativement élevée. Point d'éclair compris entre 38 °C et 93 °C.">2</span></a></div><div style="width: 37.5px; height: 2em; text-align: center; vertical-align: middle; position: absolute; top: 33px; font-size: large;"><a href="/wiki/NFPA_704#Santé2" title="NFPA 704"><span style="color: black;" title="Produit pouvant provoquer après une exposition intense ou continue (mais non chronique), une incapacité temporaire ou une séquelle mineure résiduelle">2</span></a></div><div style="width: 37.5px; height: 2em; text-align: center; vertical-align: middle; position: absolute; top: 33px; left: 37.5px; font-size: large;"><a href="/wiki/NFPA_704#Réactivité1" title="NFPA 704"><span style="color: black;" title="Produit stable, mais pouvant devenir instable à température et pression élevées">1</span></a></div><div style="width: 75px; height: 2em; text-align: center; vertical-align: middle; position: absolute; top: 52px; font-size: small;"><small></small></div></div></div></td> </tr><tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#eeeeee; color:#000000"><a href="/wiki/Directive_67/548/EEC" title="Directive 67/548/EEC">Directive 67/548/EEC</a></th></tr> <tr> <td colspan="2" style="text-align:left;"><div class="NavFrame" title="[+]/[–]" style="clear:left; border:none; padding: 0;"><div class="NavContent" style="display:none; text-align:left;"><b>Phrases R</b> : <br /><b>R10</b> : Inflammable.<br /><b>R20</b> : Nocif par inhalation.<br /><b>R25</b> : Toxique en cas d’ingestion.<br /><b>R41</b> : Risque de lésions oculaires graves.<br /><br /><b>Phrases S</b> : <br /><b>S26</b> : En cas de contact avec les yeux, laver immédiatement et abondamment avec de l’eau et consulter un spécialiste.<br /><b>S45</b> : En cas d’accident ou de malaise, consulter immédiatement un médecin (si possible, lui montrer l’étiquette).<br /><b>S37/39</b> : Porter des gants appropriés et un appareil de protection des yeux/du visage.<br /></div></div><br /><div style="clear:left;"><a href="/wiki/Phrases_de_risque" title="Phrases de risque">Phrases R</a> : <a href="/wiki/Phrases_de_risque#R10" title="Phrases de risque"><span title="Inflammable.">10, </span></a><a href="/wiki/Phrases_de_risque#R20" title="Phrases de risque"><span title="Nocif par inhalation">20, </span></a><a href="/wiki/Phrases_de_risque#R25" title="Phrases de risque"><span title="Toxique en cas d’ingestion.">25, </span></a><a href="/wiki/Phrases_de_risque#R41" title="Phrases de risque"><span title="Risque de lésions oculaires graves.">41, </span></a></div><br /><div style="clear:left;"><a href="/wiki/Conseils_de_prudence" title="Conseils de prudence">Phrases S</a> : <a href="/wiki/Conseils_de_prudence#S26" title="Conseils de prudence"><span title="En cas de contact avec les yeux, laver immédiatement et abondamment avec de l’eau et consulter un spécialiste.">26, </span></a><a href="/wiki/Conseils_de_prudence#S37.2F39" title="Conseils de prudence"><span title="Porter des gants appropriés et un appareil de protection des yeux/du visage.">37/39, </span></a><a href="/wiki/Conseils_de_prudence#S45" title="Conseils de prudence"><span title="En cas d’accident ou de malaise, consulter immédiatement un médecin (si possible, lui montrer l’étiquette).">45, </span></a></div></td> </tr><tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#eeeeee; color:#000000"><a href="/wiki/Accord_relatif_au_transport_international_des_marchandises_dangereuses_par_route" title="Accord relatif au transport international des marchandises dangereuses par route">Transport</a></th></tr> <tr> <td colspan="2" style="text-align:center;"><div class="center"><table class="wikitable centre" style="width:33px margin:0px; background-color:#ff950e; border: 1px solid black;"><tbody><tr><td width="100%" style="background-color:#ff950e; border: 1px solid black;"><div style="text-align:center"><a href="/wiki/Liste_des_codes_Kemler" title="Liste des codes Kemler"><span style="color: black;">33/30</span></a></div></td></tr><tr><td width="100%" style="background-color:#ff950e; border: 1px solid black;"><div style="text-align:center">   <a href="/wiki/Liste_des_num%C3%A9ros_ONU" title="Liste des numéros ONU"><span style="color: black;" title="numéro ONU">1993</span></a>   </div></td></tr></tbody></table><div class="NavFrame" title="[+]/[–]" style="border:none; padding: 0;"><div class="NavContent" style="display:none; text-align:left;"><b>Code Kemler :</b><br />33/30<br /><b><a href="/wiki/Num%C3%A9ro_ONU" title="Numéro ONU">Numéro ONU</a> :</b><br /><b><a href="/wiki/Liste_des_num%C3%A9ros_ONU" title="Liste des numéros ONU">1993</a></b> : LIQUIDE INFLAMMABLE, N.S.A.<br /><b>Classe :</b><br />3<br /><b>Étiquette :</b><br /><span typeof="mw:File"><a href="/wiki/Fichier:ADR_3.svg" class="mw-file-description"><img alt="pictogramme ADR 3" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/ADR_3.svg/75px-ADR_3.svg.png" decoding="async" width="75" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/94/ADR_3.svg/113px-ADR_3.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/94/ADR_3.svg/150px-ADR_3.svg.png 2x" data-file-width="104" data-file-height="103" /></a></span><br /><b>3</b> : Liquides inflammables<br /></div></div></div></td> </tr><tr> <th colspan="2" style="padding:4px; text-align:center; background-color:#ffb4b4; color:#000000"><a href="/wiki/%C3%89cotoxicologie" title="Écotoxicologie">Écotoxicologie</a></th></tr> <tr> <th scope="row"><a href="/wiki/LogP" title="LogP">LogP</a> </th> <td>0,75<sup id="cite_ref-HSDB_4-6" class="reference"><a href="#cite_note-HSDB-4"><span class="cite_crochet">[</span>4<span class="cite_crochet">]</span></a></sup> </td> </tr> <tr> <td colspan="2"><hr style="height:2px; background-color:#FFDEAD;" /></td></tr> <tr> <td colspan="2" style="text-align:center;">Unités du <a href="/wiki/Syst%C3%A8me_international_d%27unit%C3%A9s" title="Système international d'unités">SI</a> et <a href="/wiki/Conditions_normales_de_temp%C3%A9rature_et_de_pression" title="Conditions normales de température et de pression"><abbr title="conditions normales de température et de pression">CNTP</abbr></a>, sauf indication contraire.</td> </tr><tr> <td class="navigation-only" colspan="2" style="border-top: 2px #FFDEAD solid; font-size: 80%; background:inherit; text-align: right;"><span class="plainlinks" style="float:left;"><a class="external text" href="https://fr.wikipedia.org/w/index.php?title=Pyrrole&action=edit&section=0"><span class="infodoc">modifier</span></a></span> <span typeof="mw:File"><a href="/wiki/Mod%C3%A8le:Infobox_Chimie" title="Consultez la documentation du modèle"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Info_Simple.svg/12px-Info_Simple.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Info_Simple.svg/18px-Info_Simple.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/38/Info_Simple.svg/24px-Info_Simple.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span></td> </tr> </tbody></table> <p>Le <b>pyrrole</b> ou <b>azole</b>, de <a href="/wiki/Formule_brute" title="Formule brute">formule brute</a> C<sub>4</sub>H<sub>5</sub>N<sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub>, est un <a href="/wiki/H%C3%A9t%C3%A9rocycle" title="Hétérocycle">composé hétérocyclique</a> simple et fondamental de la classe des <a href="/wiki/M%C3%A9tallole" title="Métallole">métalloles</a>, constitué d'un cycle aromatique de 5 atomes dont un <a href="/wiki/Atome" title="Atome">atome</a> d'<a href="/wiki/Azote" title="Azote">azote</a>. Le pyrrole est un <a href="/wiki/Hydrocarbure_aromatique" title="Hydrocarbure aromatique">composé aromatique</a> qui possède une réactivité différente du <a href="/wiki/Benz%C3%A8ne" title="Benzène">benzène</a>. Il est utilisé en tant que <a href="/wiki/R%C3%A9actif_(chimie)" title="Réactif (chimie)">réactif</a> ou précurseur en <a href="/wiki/Chimie_organique" title="Chimie organique">chimie organique</a>. Il fut découvert par <a href="/wiki/Friedlieb_Ferdinand_Runge" title="Friedlieb Ferdinand Runge">Runge</a> dans les <a href="/w/index.php?title=Huile_empyreumatique&action=edit&redlink=1" class="new" title="Huile empyreumatique (page inexistante)">huiles empyreumatiques</a> issues de la <a href="/wiki/Distillation_s%C3%A8che" title="Distillation sèche">distillation sèche</a> des os. On peut aussi l'extraire de l'huile animale de Dippel. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Biochimie_du_noyau_pyrrole">Biochimie du noyau pyrrole</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrrole&veaction=edit&section=1" title="Modifier la section : Biochimie du noyau pyrrole" class="mw-editsection-visualeditor"><span>modifier</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Pyrrole&action=edit&section=1" title="Modifier le code source de la section : Biochimie du noyau pyrrole"><span>modifier le code</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Les pyrroles sont les composés les plus importants parmi ceux possédant un cycle aromatique. Ils entrent dans la structure des <a href="/wiki/Porphyrine" title="Porphyrine">porphyrines</a> telles que l'<a href="/wiki/H%C3%A8me" title="Hème">hème</a>, des <a href="/wiki/Chlorine" title="Chlorine">chlorines</a> telles que la <a href="/wiki/Chlorophylle" title="Chlorophylle">chlorophylle</a> et du noyau <a href="/wiki/Corrine" title="Corrine">corrine</a> de la <a href="/wiki/Vitamine_B12" title="Vitamine B12">vitamine B<sub>12</sub></a>. </p> <div class="mw-heading mw-heading2"><h2 id="Aromaticité"><span id="Aromaticit.C3.A9"></span>Aromaticité</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrrole&veaction=edit&section=2" title="Modifier la section : Aromaticité" class="mw-editsection-visualeditor"><span>modifier</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Pyrrole&action=edit&section=2" title="Modifier le code source de la section : Aromaticité"><span>modifier le code</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Le pyrrole est un <a href="/wiki/Compos%C3%A9_aromatique" title="Composé aromatique">composé aromatique</a> qui respecte la <a href="/wiki/R%C3%A8gle_de_H%C3%BCckel" title="Règle de Hückel">règle de Hückel</a>. Les <a href="/wiki/%C3%89lectron" title="Électron">électrons</a> délocalisés sont ceux des deux <a href="/wiki/Double_liaison" class="mw-redirect" title="Double liaison">double liaisons</a> ainsi que les deux électrons du <a href="/wiki/Doublet" class="mw-disambig" title="Doublet">doublet</a> libre de l'azote, soit six électrons en tout. Chaque carbone apporte un de ses électrons pi dans la délocalisation et l’azote apporte deux électrons. Les carbones sont hybridés sp². Le pyrrole possède une énergie de résonance de 100 <a href="/wiki/Kilojoule" class="mw-redirect" title="Kilojoule">kJ</a> par <a href="/wiki/Mole_(unit%C3%A9)" title="Mole (unité)">mole</a>. Cette énergie est inférieure à celle du <a href="/wiki/Benz%C3%A8ne" title="Benzène">benzène</a> et du <a href="/wiki/Thioph%C3%A8ne" title="Thiophène">thiophène</a>, mais supérieure à celle du <a href="/wiki/Furane" title="Furane">furane</a><sup id="cite_ref-Chimie_organique_hétérocyclique_structures_fondamentales_7-0" class="reference"><a href="#cite_note-Chimie_organique_hétérocyclique_structures_fondamentales-7"><span class="cite_crochet">[</span>7<span class="cite_crochet">]</span></a></sup>. Le pyrrole est un composé moins aromatique que le benzène et le thiophène mais plus aromatique que le <a href="/wiki/Furane" title="Furane">furane</a>. </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/Fichier:Pyrrole_Resonance.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Pyrrole_Resonance.png/700px-Pyrrole_Resonance.png" decoding="async" width="700" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Pyrrole_Resonance.png/1050px-Pyrrole_Resonance.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Pyrrole_Resonance.png/1400px-Pyrrole_Resonance.png 2x" data-file-width="4400" data-file-height="538" /></a><figcaption>Formes mésomères du pyrrole</figcaption></figure> <div class="clear" style="clear:left;"></div> <div class="mw-heading mw-heading2"><h2 id="Bibliographie">Bibliographie</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrrole&veaction=edit&section=3" title="Modifier la section : Bibliographie" class="mw-editsection-visualeditor"><span>modifier</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Pyrrole&action=edit&section=3" title="Modifier le code source de la section : Bibliographie"><span>modifier le code</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><abbr class="abbr indicateur-langue" title="Langue : français">(fr)</abbr> R.Milcent, F.Chau <i>Chimie Organique Hétérocyclique</i>, <a href="/wiki/EDP_Sciences" title="EDP Sciences">EDP Sciences</a>.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Notes_et_références"><span id="Notes_et_r.C3.A9f.C3.A9rences"></span>Notes et références</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrrole&veaction=edit&section=4" title="Modifier la section : Notes et références" class="mw-editsection-visualeditor"><span>modifier</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Pyrrole&action=edit&section=4" title="Modifier le code source de la section : Notes et références"><span>modifier le code</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="references-small decimal" style=""><div class="mw-references-wrap"><ol class="references"> <li id="cite_note-HandbookChemPhys89ed-1"><span class="mw-cite-backlink noprint"><a href="#cite_ref-HandbookChemPhys89ed_1-0">↑</a> </span><span class="reference-text"><span class="ouvrage" id="Lide2008"><span class="ouvrage" id="David_R._Lide2008"><abbr class="abbr indicateur-langue" title="Langue : anglais">(en)</abbr> David R. Lide, <cite class="italique" lang="en">Handbook of chemistry and physics</cite>, Boca Raton, CRC, <time class="nowrap" datetime="2008-06-16" data-sort-value="2008-06-16">16 juin 2008</time>, <abbr class="abbr" title="quatre-vingt-neuvième">89<sup>e</sup></abbr> <abbr class="abbr" title="édition">éd.</abbr>, 2736 <abbr class="abbr" title="pages">p.</abbr> <small style="line-height:1em;">(<a href="/wiki/International_Standard_Book_Number" title="International Standard Book Number">ISBN</a> <a href="/wiki/Sp%C3%A9cial:Ouvrages_de_r%C3%A9f%C3%A9rence/978-1-4200-6679-1" title="Spécial:Ouvrages de référence/978-1-4200-6679-1"><span class="nowrap">978-1-4200-6679-1</span></a> et <a href="/wiki/Sp%C3%A9cial:Ouvrages_de_r%C3%A9f%C3%A9rence/1-4200-6679-X" title="Spécial:Ouvrages de référence/1-4200-6679-X"><span class="nowrap">1-4200-6679-X</span></a>)</small>, <abbr class="abbr" title="pages">p.</abbr> <span class="nowrap">9-50</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Handbook+of+chemistry+and+physics&rft.place=Boca+Raton&rft.pub=CRC&rft.edition=89&rft.aulast=Lide&rft.aufirst=David+R.&rft.date=2008-06-16&rft.pages=9-50&rft.tpages=2736&rft.isbn=978-1-4200-6679-1&rfr_id=info%3Asid%2Ffr.wikipedia.org%3APyrrole"></span></span></span>.</span> </li> <li id="cite_note-Yitzhak_Marcus-2"><span class="mw-cite-backlink noprint">↑ <sup><a href="#cite_ref-Yitzhak_Marcus_2-0">a</a> et <a href="#cite_ref-Yitzhak_Marcus_2-1">b</a></sup> </span><span class="reference-text"><span class="ouvrage" id="Marcus1999"><span class="ouvrage" id="Yitzhak_Marcus1999"><abbr class="abbr indicateur-langue" title="Langue : anglais">(en)</abbr> Yitzhak Marcus, <cite class="italique" lang="en">The Properties of Solvents</cite>, <abbr class="abbr" title="volume">vol.</abbr> 4, England, John Wiley & Sons Ltd, <time>1999</time>, 239 <abbr class="abbr" title="pages">p.</abbr> <small style="line-height:1em;">(<a href="/wiki/International_Standard_Book_Number" title="International Standard Book Number">ISBN</a> <a href="/wiki/Sp%C3%A9cial:Ouvrages_de_r%C3%A9f%C3%A9rence/0-471-98369-1" title="Spécial:Ouvrages de référence/0-471-98369-1"><span class="nowrap">0-471-98369-1</span></a>)</small><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Properties+of+Solvents&rft.place=England&rft.pub=John+Wiley+%26+Sons+Ltd&rft.aulast=Marcus&rft.aufirst=Yitzhak&rft.date=1999&rft.volume=4&rft.tpages=239&rft.isbn=0-471-98369-1&rfr_id=info%3Asid%2Ffr.wikipedia.org%3APyrrole"></span></span></span>.</span> </li> <li id="cite_note-3"><span class="mw-cite-backlink noprint"><a href="#cite_ref-3">↑</a> </span><span class="reference-text">Masse molaire calculée d’après <span class="ouvrage">« <a rel="nofollow" class="external text" href="http://www.chem.qmul.ac.uk/iupac/AtWt/"><cite style="font-style:normal;"><span class="lang-en" lang="en">Atomic weights of the elements 2007</span></cite></a> », sur <span class="italique">www.chem.qmul.ac.uk</span></span>.</span> </li> <li id="cite_note-HSDB-4"><span class="mw-cite-backlink noprint">↑ <sup><a href="#cite_ref-HSDB_4-0">a</a> <a href="#cite_ref-HSDB_4-1">b</a> <a href="#cite_ref-HSDB_4-2">c</a> <a href="#cite_ref-HSDB_4-3">d</a> <a href="#cite_ref-HSDB_4-4">e</a> <a href="#cite_ref-HSDB_4-5">f</a> et <a href="#cite_ref-HSDB_4-6">g</a></sup> </span><span class="reference-text"><span class="ouvrage">« <a rel="nofollow" class="external text" href="http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+@rel+109-97-7"><cite style="font-style:normal;">PYRROLE</cite></a> », sur <span class="italique">Hazardous Substances Data Bank</span> <small style="line-height:1em;">(consulté le <time class="nowrap" datetime="2009-12-14" data-sort-value="2009-12-14">14 décembre 2009</time>)</small></span>.</span> </li> <li id="cite_note-Yaws-5"><span class="mw-cite-backlink noprint"><a href="#cite_ref-Yaws_5-0">↑</a> </span><span class="reference-text"><span class="ouvrage" id="Yaws1996"><span class="ouvrage" id="Carl_L._Yaws1996"><abbr class="abbr indicateur-langue" title="Langue : anglais">(en)</abbr> Carl L. Yaws, <cite class="italique" lang="en">Handbook of Thermodynamic Diagrams : Organic Compounds C8 to C28</cite>, <abbr class="abbr" title="volume">vol.</abbr> 1, Huston, Texas, Gulf Pub. Co., <time>1996</time>, 396 <abbr class="abbr" title="pages">p.</abbr> <small style="line-height:1em;">(<a href="/wiki/International_Standard_Book_Number" title="International Standard Book Number">ISBN</a> <a href="/wiki/Sp%C3%A9cial:Ouvrages_de_r%C3%A9f%C3%A9rence/0-88415-857-8" title="Spécial:Ouvrages de référence/0-88415-857-8"><span class="nowrap">0-88415-857-8</span></a>)</small><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Handbook+of+Thermodynamic+Diagrams&rft.place=Huston%2C+Texas&rft.pub=Gulf+Pub.+Co.&rft.stitle=Organic+Compounds+C8+to+C28&rft.aulast=Yaws&rft.aufirst=Carl+L.&rft.date=1996&rft.volume=1&rft.tpages=396&rft.isbn=0-88415-857-8&rfr_id=info%3Asid%2Ffr.wikipedia.org%3APyrrole"></span></span></span>.</span> </li> <li id="cite_note-ouvrage-6"><span class="mw-cite-backlink noprint"><a href="#cite_ref-ouvrage_6-0">↑</a> </span><span class="reference-text"><span class="ouvrage" id="Lide2008"><span class="ouvrage" id="David_R._Lide2008"><abbr class="abbr indicateur-langue" title="Langue : anglais">(en)</abbr> David R. Lide, <cite class="italique" lang="en">Handbook of chemistry and physics</cite>, CRC, <time>2008</time>, <abbr class="abbr" title="quatre-vingt-neuvième">89<sup>e</sup></abbr> <abbr class="abbr" title="édition">éd.</abbr>, 2736 <abbr class="abbr" title="pages">p.</abbr> <small style="line-height:1em;">(<a href="/wiki/International_Standard_Book_Number" title="International Standard Book Number">ISBN</a> <a href="/wiki/Sp%C3%A9cial:Ouvrages_de_r%C3%A9f%C3%A9rence/978-1-4200-6679-1" title="Spécial:Ouvrages de référence/978-1-4200-6679-1"><span class="nowrap">978-1-4200-6679-1</span></a>)</small>, <abbr class="abbr" title="pages">p.</abbr> <span class="nowrap">10-205</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Handbook+of+chemistry+and+physics&rft.pub=CRC&rft.edition=89&rft.aulast=Lide&rft.aufirst=David+R.&rft.date=2008&rft.pages=10-205&rft.tpages=2736&rft.isbn=978-1-4200-6679-1&rfr_id=info%3Asid%2Ffr.wikipedia.org%3APyrrole"></span></span></span>.</span> </li> <li id="cite_note-Chimie_organique_hétérocyclique_structures_fondamentales-7"><span class="mw-cite-backlink noprint"><a href="#cite_ref-Chimie_organique_hétérocyclique_structures_fondamentales_7-0">↑</a> </span><span class="reference-text">Chimie organique hétérocyclique structures fondamentales.</span> </li> </ol></div> </div> <div class="mw-heading mw-heading2"><h2 id="Liens_externes">Liens externes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrrole&veaction=edit&section=5" title="Modifier la section : Liens externes" class="mw-editsection-visualeditor"><span>modifier</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Pyrrole&action=edit&section=5" title="Modifier le code source de la section : Liens externes"><span>modifier le code</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external autonumber" href="http://www.sciencedirect.com/science?_ob=PublicationURL&_tockey=%23TOC%235289%232006%23999379949%23636416%23FLA%23&_cdi=5289&_pubType=J&view=c&_auth=y&_acct=C000043357&_version=1&_urlVersion=0&_userid=789722&md5=b22786bd8332b5d556d8620f8928ca28">[1]</a> Revue récente de la littérature sur les groupements protecteurs des pyrroles (p. 11531)</li></ul> <div class="mw-heading mw-heading2"><h2 id="Voir_aussi">Voir aussi</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Pyrrole&veaction=edit&section=6" title="Modifier la section : Voir aussi" class="mw-editsection-visualeditor"><span>modifier</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Pyrrole&action=edit&section=6" title="Modifier le code source de la section : Voir aussi"><span>modifier le code</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Composés structurellement ou chimiquement apparentés : </p> <ul><li><a href="/wiki/Pyrrolidine" title="Pyrrolidine">Pyrrolidine</a>, pyrrole saturé</li> <li><a href="/wiki/Pyrroline" class="mw-redirect" title="Pyrroline">Pyrroline</a>, pyrrole partiellement saturé</li> <li><b>Pyrroles substitués</b></li> <li><b>Pyrrole liés à des cycles</b> <ul><li><a href="/wiki/Indole" title="Indole">Indole</a>, pyrrole lié à un <a href="/wiki/Benz%C3%A8ne" title="Benzène">benzène</a></li></ul></li> <li><b>Analogues du pyrrole</b> <ul><li><a href="/wiki/Furane" title="Furane">Furane</a>, hétérocyclique avec un atome d'<a href="/wiki/Oxyg%C3%A8ne" title="Oxygène">oxygène</a></li> <li><a href="/wiki/Thioph%C3%A8ne" title="Thiophène">Thiophène</a>, hétérocyclique avec un atome de <a href="/wiki/Soufre" title="Soufre">soufre</a></li> <li><a href="/wiki/S%C3%A9l%C3%A9noph%C3%A8ne" title="Sélénophène">Sélénophène</a>, hétérocyclique avec un atome de <a href="/wiki/S%C3%A9l%C3%A9nium" title="Sélénium">sélénium</a></li> <li><a href="/w/index.php?title=Telluroph%C3%A8ne&action=edit&redlink=1" class="new" title="Tellurophène (page inexistante)">Tellurophène</a>, hétérocyclique avec un atome de <a href="/wiki/Tellure" title="Tellure">tellure</a></li></ul></li></ul> <ul id="bandeau-portail" class="bandeau-portail"><li><span class="bandeau-portail-element"><span class="bandeau-portail-icone"><span class="noviewer" typeof="mw:File"><a href="/wiki/Portail:Chimie" title="Portail de la chimie"><img alt="icône décorative" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Nuvola_apps_edu_science.svg/24px-Nuvola_apps_edu_science.svg.png" decoding="async" width="24" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Nuvola_apps_edu_science.svg/36px-Nuvola_apps_edu_science.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/59/Nuvola_apps_edu_science.svg/48px-Nuvola_apps_edu_science.svg.png 2x" data-file-width="128" data-file-height="128" /></a></span></span> <span class="bandeau-portail-texte"><a href="/wiki/Portail:Chimie" title="Portail:Chimie">Portail de la chimie</a></span> </span></li> <li><span class="bandeau-portail-element"><span class="bandeau-portail-icone"><span class="noviewer" typeof="mw:File"><a href="/wiki/Portail:Biochimie" title="Portail de la biochimie"><img alt="icône décorative" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Hemoglobin.jpg/26px-Hemoglobin.jpg" decoding="async" width="26" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Hemoglobin.jpg/39px-Hemoglobin.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/19/Hemoglobin.jpg/52px-Hemoglobin.jpg 2x" data-file-width="418" data-file-height="386" /></a></span></span> <span class="bandeau-portail-texte"><a href="/wiki/Portail:Biochimie" title="Portail:Biochimie">Portail de la biochimie</a></span> </span></li> </ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Ce document provient de « <a dir="ltr" href="https://fr.wikipedia.org/w/index.php?title=Pyrrole&oldid=202547269">https://fr.wikipedia.org/w/index.php?title=Pyrrole&oldid=202547269</a> ».</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Cat%C3%A9gorie:Accueil" title="Catégorie:Accueil">Catégories</a> : <ul><li><a href="/wiki/Cat%C3%A9gorie:Noyau_aromatique_simple" 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