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<li id="toc-Note" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Note"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Note</span> </div> </a> <ul id="toc-Note-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bibliografia" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Bibliografia"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Bibliografia</span> </div> </a> <ul id="toc-Bibliografia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Voci_correlate" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Voci_correlate"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Voci correlate</span> </div> </a> <ul id="toc-Voci_correlate-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Altri_progetti" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Altri_progetti"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Altri progetti</span> </div> </a> <ul id="toc-Altri_progetti-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="Indice" 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="Mostra/Nascondi l'indice" > <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">Mostra/Nascondi l'indice</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">Stereoselettività</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="Vai a una voce in un'altra lingua. Disponibile in 19 lingue" > <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-19" 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">19 lingue</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Estereoselectivitat" title="Estereoselectivitat - catalano" lang="ca" hreflang="ca" data-title="Estereoselectivitat" data-language-autonym="Català" data-language-local-name="catalano" 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/Stereoselektivita" title="Stereoselektivita - ceco" lang="cs" hreflang="cs" data-title="Stereoselektivita" data-language-autonym="Čeština" data-language-local-name="ceco" 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/Stereoselektivit%C3%A4t" title="Stereoselektivität - tedesco" lang="de" hreflang="de" data-title="Stereoselektivität" data-language-autonym="Deutsch" data-language-local-name="tedesco" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Stereoselectivity" title="Stereoselectivity - inglese" lang="en" hreflang="en" data-title="Stereoselectivity" data-language-autonym="English" data-language-local-name="inglese" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Estereoselectividad" title="Estereoselectividad - spagnolo" lang="es" hreflang="es" data-title="Estereoselectividad" data-language-autonym="Español" data-language-local-name="spagnolo" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Stereoselektiivsus" title="Stereoselektiivsus - estone" lang="et" hreflang="et" data-title="Stereoselektiivsus" data-language-autonym="Eesti" data-language-local-name="estone" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Estereoselektibitate" title="Estereoselektibitate - basco" lang="eu" hreflang="eu" data-title="Estereoselektibitate" data-language-autonym="Euskara" data-language-local-name="basco" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Sp%C3%A9cificit%C3%A9_et_s%C3%A9lectivit%C3%A9" title="Spécificité et sélectivité - francese" lang="fr" hreflang="fr" data-title="Spécificité et sélectivité" data-language-autonym="Français" data-language-local-name="francese" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A1%D7%98%D7%A8%D7%99%D7%90%D7%95%D7%A1%D7%9C%D7%A7%D7%98%D7%99%D7%91%D7%99%D7%95%D7%AA" title="סטריאוסלקטיביות - ebraico" lang="he" hreflang="he" data-title="סטריאוסלקטיביות" data-language-autonym="עברית" data-language-local-name="ebraico" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E7%AB%8B%E4%BD%93%E9%81%B8%E6%8A%9E%E6%80%A7" title="立体選択性 - giapponese" lang="ja" hreflang="ja" data-title="立体選択性" data-language-autonym="日本語" data-language-local-name="giapponese" 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/%EC%9E%85%EC%B2%B4%EC%84%A0%ED%83%9D%EC%84%B1" title="입체선택성 - coreano" lang="ko" hreflang="ko" data-title="입체선택성" data-language-autonym="한국어" data-language-local-name="coreano" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Stereoselectiviteit" title="Stereoselectiviteit - olandese" lang="nl" hreflang="nl" data-title="Stereoselectiviteit" data-language-autonym="Nederlands" data-language-local-name="olandese" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Estereosseletividade" title="Estereosseletividade - portoghese" lang="pt" hreflang="pt" data-title="Estereosseletividade" data-language-autonym="Português" data-language-local-name="portoghese" 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/Stereoselectivitate" title="Stereoselectivitate - rumeno" lang="ro" hreflang="ro" data-title="Stereoselectivitate" data-language-autonym="Română" data-language-local-name="rumeno" 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%A1%D1%82%D0%B5%D1%80%D0%B5%D0%BE%D1%81%D0%B5%D0%BB%D0%B5%D0%BA%D1%82%D0%B8%D0%B2%D0%BD%D0%BE%D1%81%D1%82%D1%8C" title="Стереоселективность - russo" lang="ru" hreflang="ru" data-title="Стереоселективность" data-language-autonym="Русский" data-language-local-name="russo" 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/Stereoselektivnost" title="Stereoselektivnost - serbo-croato" lang="sh" hreflang="sh" data-title="Stereoselektivnost" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="serbo-croato" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A1%D1%82%D0%B5%D1%80%D0%B5%D0%BE%D1%81%D0%B5%D0%BB%D0%B5%D0%BA%D1%82%D0%B8%D0%B2%D0%BD%D0%BE%D1%81%D1%82" title="Стереоселективност - serbo" lang="sr" hreflang="sr" data-title="Стереоселективност" data-language-autonym="Српски / srpski" data-language-local-name="serbo" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A1%D1%82%D0%B5%D1%80%D0%B5%D0%BE%D1%81%D0%B5%D0%BB%D0%B5%D0%BA%D1%82%D0%B8%D0%B2%D0%BD%D1%96%D1%81%D1%82%D1%8C" title="Стереоселективність - ucraino" lang="uk" hreflang="uk" data-title="Стереоселективність" data-language-autonym="Українська" data-language-local-name="ucraino" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%AB%8B%E4%BD%93%E9%80%89%E6%8B%A9%E6%80%A7" title="立体选择性 - cinese" lang="zh" hreflang="zh" data-title="立体选择性" data-language-autonym="中文" data-language-local-name="cinese" 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/Q903429#sitelinks-wikipedia" title="Modifica collegamenti interlinguistici" class="wbc-editpage">Modifica collegamenti</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="Namespace"> <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"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Stereoselettivit%C3%A0" title="Vedi la voce [c]" accesskey="c"><span>Voce</span></a></li><li id="ca-talk" class="new vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Discussione:Stereoselettivit%C3%A0&action=edit&redlink=1" rel="discussion" class="new" title="Vedi le discussioni relative a questa pagina (la pagina non esiste) [t]" accesskey="t"><span>Discussione</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" 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class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Stereoselettivit%C3%A0"><span>Leggi</span></a></li><li id="ca-ve-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Stereoselettivit%C3%A0&veaction=edit" title="Modifica questa pagina [v]" accesskey="v"><span>Modifica</span></a></li><li id="ca-edit" class="collapsible vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Stereoselettivit%C3%A0&action=edit" title="Modifica il wikitesto di questa pagina [e]" accesskey="e"><span>Modifica wikitesto</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Stereoselettivit%C3%A0&action=history" title="Versioni precedenti di questa pagina [h]" accesskey="h"><span>Cronologia</span></a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Strumenti pagine"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" 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> <div class="vector-pinnable-header-label">Strumenti</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">sposta nella barra laterale</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">nascondi</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="Altre opzioni" > <div class="vector-menu-heading"> Azioni </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/Stereoselettivit%C3%A0"><span>Leggi</span></a></li><li id="ca-more-ve-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Stereoselettivit%C3%A0&veaction=edit" title="Modifica questa pagina [v]" accesskey="v"><span>Modifica</span></a></li><li id="ca-more-edit" class="collapsible vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Stereoselettivit%C3%A0&action=edit" title="Modifica il wikitesto di questa pagina [e]" accesskey="e"><span>Modifica wikitesto</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Stereoselettivit%C3%A0&action=history"><span>Cronologia</span></a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> Generale </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Speciale:PuntanoQui/Stereoselettivit%C3%A0" title="Elenco di tutte le pagine che sono collegate a questa [j]" accesskey="j"><span>Puntano qui</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Speciale:ModificheCorrelate/Stereoselettivit%C3%A0" rel="nofollow" title="Elenco delle ultime modifiche alle pagine collegate a questa [k]" accesskey="k"><span>Modifiche correlate</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Speciale:PagineSpeciali" title="Elenco di tutte le pagine speciali [q]" accesskey="q"><span>Pagine speciali</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Stereoselettivit%C3%A0&oldid=135783970" title="Collegamento permanente a questa versione di questa pagina"><span>Link permanente</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Stereoselettivit%C3%A0&action=info" title="Ulteriori informazioni su questa pagina"><span>Informazioni pagina</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Speciale:Cita&page=Stereoselettivit%C3%A0&id=135783970&wpFormIdentifier=titleform" title="Informazioni su come citare questa pagina"><span>Cita questa voce</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Speciale:UrlShortener&url=https%3A%2F%2Fit.wikipedia.org%2Fwiki%2FStereoselettivit%25C3%25A0"><span>Ottieni URL breve</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Speciale:QrCode&url=https%3A%2F%2Fit.wikipedia.org%2Fwiki%2FStereoselettivit%25C3%25A0"><span>Scarica codice 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"> Stampa/esporta </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=Speciale:Libro&bookcmd=book_creator&referer=Stereoselettivit%C3%A0"><span>Crea un libro</span></a></li><li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Speciale:DownloadAsPdf&page=Stereoselettivit%C3%A0&action=show-download-screen"><span>Scarica come PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Stereoselettivit%C3%A0&printable=yes" title="Versione stampabile di questa pagina [p]" accesskey="p"><span>Versione stampabile</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"> In altri progetti </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:Stereoselectivity" 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/Q903429" title="Collegamento all'elemento connesso dell'archivio dati [g]" accesskey="g"><span>Elemento 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="Strumenti pagine"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Aspetto"> <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">Aspetto</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">sposta nella barra laterale</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">nascondi</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">Da Wikipedia, l'enciclopedia libera.</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="it" dir="ltr"><p>In <a href="/wiki/Chimica" title="Chimica">chimica</a> la <b>stereoselettività</b> è la proprietà di una <a href="/wiki/Reazione_chimica" title="Reazione chimica">reazione</a> di produrre preferenzialmente un particolare <a href="/wiki/Stereoisomero" title="Stereoisomero">stereoisomero</a>, nonostante si parta da un singolo reagente trattato con un processo <a href="/wiki/Stereospecificit%C3%A0" title="Stereospecificità">non-stereospecifico</a> che potrebbe dare più <a href="/wiki/Stereoisomero" title="Stereoisomero">stereoisomeri</a>. È importante non confondere la stereoselettività con la <a href="/wiki/Stereospecificit%C3%A0" title="Stereospecificità">stereospecificità</a>, che si basa invece sull'uso iniziale di un particolare stereoisomero in modo da poter controllare il prodotto finale della reazione. </p><p>La stereoselettività nasce dalle differenze negli effetti <a href="/wiki/Ingombro_sterico" title="Ingombro sterico">sterici</a> ed elettronici fra i diversi meccanismi che portano ai differenti stereoisomeri. Uno o più di questi verranno prediletti per via di una più bassa <a href="/wiki/Energia_di_attivazione" title="Energia di attivazione">energia di attivazione</a>. Quando i prodotti finali sono <a href="/wiki/Diastereoisomero" title="Diastereoisomero">diastereoisomeri</a> si misura la preferenza della reazione tramite l'<a href="/w/index.php?title=Eccesso_diastereomerico&action=edit&redlink=1" class="new" title="Eccesso diastereomerico (la pagina non esiste)">eccesso diastereomerico</a>. </p><p>Si parla di <b>enantioselettività</b> quando i prodotti finali sono <a href="/wiki/Enantiomeri" class="mw-redirect" title="Enantiomeri">enantiomeri</a> e la reazione produce un <a href="/wiki/Eccesso_enantiomerico" title="Eccesso enantiomerico">eccesso enantiomerico</a>: in questo caso è necessario utilizzare un reagente o un catalizzatore <a href="/wiki/Chiralit%C3%A0_(chimica)" title="Chiralità (chimica)">chirale</a>, poiché è impossibile introdurre enantioselettività partendo da un <a href="/wiki/Racemo_(chimica)" title="Racemo (chimica)">racemo</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Definizione_IUPAC">Definizione IUPAC</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stereoselettivit%C3%A0&veaction=edit&section=1" title="Modifica la sezione Definizione IUPAC" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Stereoselettivit%C3%A0&action=edit&section=1" title="Edit section's source code: Definizione IUPAC"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r139517313">.mw-parser-output .itwiki-template-citazione{margin-bottom:.5em;font-size:95%;padding-left:2.4em;padding-right:1.2em}.mw-parser-output .itwiki-template-citazione-doppia{display:flex;gap:1.2em}.mw-parser-output .itwiki-template-citazione-doppia>div{width:0;flex:1 1 0}.mw-parser-output .itwiki-template-citazione-footer{padding:0 1.2em 0 0;margin:0}</style><div class="itwiki-template-citazione"> <div class="itwiki-template-citazione-singola"> <p>«<b>Stereoselectivity</b>: The preferential formation in a chemical reaction of one stereoisomer over another. When the stereoisomers are enantiomers, the phenomenon is called enantioselectivity and is quantitatively expressed by the enantiomer excess; when they are diastereoisomers, it is called diastereoselectivity and is quantitatively expressed by the diastereoisomer excess» </p> </div><p class="itwiki-template-citazione-footer">(<small>IUPAC Gold Book (<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) <sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></small>)</p></div> <p><b>Stereoselettività</b>: La formazione preferenziale, in una reazione chimica, di uno stereoisomero piuttosto che un altro. Quando gli stereoisomeri sono enantiomeri, il fenomeno è chiamato <i>enantioselettività</i> ed è quantitativamente espresso da un eccesso di un enantiomero; quando sono diastereoisomeri, è chiamato <i>diastereoselettività</i> ed è quantitativamente espresso da un eccesso di un diastereoisomero. <sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Esempio">Esempio</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stereoselettivit%C3%A0&veaction=edit&section=2" title="Modifica la sezione Esempio" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Stereoselettivit%C3%A0&action=edit&section=2" title="Edit section's source code: Esempio"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>La seguente deidroalogenazione del 2-iodobutano (il reagente è un racemo) forma 60% <i>trans</i>-2-butene e 20% <i>cis</i>-2-butene per via della preferenza ai livelli sterici ed elettronici di avere i due gruppi metili in posizione anti durante il meccanismo di <a href="/wiki/Reazione_di_eliminazione" title="Reazione di eliminazione">eliminazione</a>. Il prodotto ulteriore, l'<a href="/wiki/1-butene" title="1-butene">1-butene</a>, è un isomero di struttura. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Stereoselectivedehalogenation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Stereoselectivedehalogenation.svg/411px-Stereoselectivedehalogenation.svg.png" decoding="async" width="411" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Stereoselectivedehalogenation.svg/617px-Stereoselectivedehalogenation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Stereoselectivedehalogenation.svg/822px-Stereoselectivedehalogenation.svg.png 2x" data-file-width="441" data-file-height="93" /></a></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Note">Note</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stereoselettivit%C3%A0&veaction=edit&section=3" title="Modifica la sezione Note" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Stereoselettivit%C3%A0&action=edit&section=3" title="Edit section's source code: Note"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><a href="#cite_ref-1"><b>^</b></a> <span class="reference-text"><a rel="nofollow" class="external text" href="http://goldbook.iupac.org/S05991.html">IUPAC Gold Book</a></span> </li> <li id="cite_note-2"><a href="#cite_ref-2"><b>^</b></a> <span class="reference-text">Traduzione italiana non ufficiale</span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Bibliografia">Bibliografia</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stereoselettivit%C3%A0&veaction=edit&section=4" title="Modifica la sezione Bibliografia" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Stereoselettivit%C3%A0&action=edit&section=4" title="Edit section's source code: Bibliografia"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><cite class="citation libro" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) Clayden, Greeves, Warren, Wothers, <span style="font-style:italic;">Organic Chemistry</span>, Oxford University Press, 2001, <a href="/wiki/ISBN" title="ISBN">ISBN</a> <a href="/wiki/Speciale:RicercaISBN/0-19-850346-6" title="Speciale:RicercaISBN/0-19-850346-6">0-19-850346-6</a>.</cite></li></ul> <div class="mw-heading mw-heading2"><h2 id="Voci_correlate">Voci correlate</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stereoselettivit%C3%A0&veaction=edit&section=5" title="Modifica la sezione Voci correlate" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Stereoselettivit%C3%A0&action=edit&section=5" title="Edit section's source code: Voci correlate"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Selettivit%C3%A0_(chimica)" title="Selettività (chimica)">Selettività (chimica)</a></li> <li><a href="/wiki/Regioselettivit%C3%A0" title="Regioselettività">Regioselettività</a></li> <li><a href="/wiki/Chemoselettivit%C3%A0" title="Chemoselettività">Chemoselettività</a></li> <li><a href="/wiki/Stereospecificit%C3%A0" title="Stereospecificità">Stereospecificità</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Altri_progetti">Altri progetti</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stereoselettivit%C3%A0&veaction=edit&section=6" title="Modifica la sezione Altri progetti" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Stereoselettivit%C3%A0&action=edit&section=6" title="Edit section's source code: Altri progetti"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <div id="interProject" class="toccolours" style="display: none; clear: both; margin-top: 2em"><p id="sisterProjects" style="background-color: #efefef; color: black; font-weight: bold; margin: 0"><span>Altri progetti</span></p><ul title="Collegamenti verso gli altri progetti Wikimedia"> <li class="" title=""><span class="plainlinks" title="commons:Category:Stereoselectivity"><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Stereoselectivity?uselang=it">Wikimedia Commons</a></span></li></ul></div> <ul><li><span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/?uselang=it" title="Collabora a Wikimedia Commons"><img alt="Collabora a Wikimedia Commons" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png" decoding="async" width="18" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/27px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/36px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span> <span class="plainlinks"><a class="external text" href="https://commons.wikimedia.org/wiki/?uselang=it">Wikimedia Commons</a></span> contiene immagini o altri file su <b><span class="plainlinks"><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Stereoselectivity?uselang=it">Stereoselettività</a></span></b></li></ul> <style data-mw-deduplicate="TemplateStyles:r141815314">.mw-parser-output .navbox{border:1px solid #aaa;clear:both;margin:auto;padding:2px;width:100%}.mw-parser-output .navbox th{padding-left:1em;padding-right:1em;text-align:center}.mw-parser-output .navbox>tbody>tr:first-child>th{background:#ccf;font-size:90%;width:100%;color:var(--color-base,black)}.mw-parser-output .navbox_navbar{float:left;margin:0;padding:0 10px 0 0;text-align:left;width:6em}.mw-parser-output .navbox_title{font-size:110%}.mw-parser-output .navbox_abovebelow{background:#ddf;font-size:90%;font-weight:normal}.mw-parser-output .navbox_group{background:#ddf;font-size:90%;padding:0 10px;white-space:nowrap}.mw-parser-output .navbox_list{font-size:90%;width:100%}.mw-parser-output .navbox_list a{white-space:nowrap}html:not(.vector-feature-night-mode-enabled) .mw-parser-output .navbox_odd{background:#fdfdfd;color:var(--color-base,black)}html:not(.vector-feature-night-mode-enabled) .mw-parser-output .navbox_even{background:#f7f7f7;color:var(--color-base,black)}.mw-parser-output .navbox a.mw-selflink{color:var(--color-base,black)}.mw-parser-output .navbox_center{text-align:center}.mw-parser-output .navbox .navbox_image{padding-left:7px;vertical-align:middle;width:0}.mw-parser-output .navbox+.navbox{margin-top:-1px}.mw-parser-output .navbox .mw-collapsible-toggle{font-weight:normal;text-align:right;width:7em}body.skin--responsive .mw-parser-output .navbox_image img{max-width:none!important}.mw-parser-output .subnavbox{margin:-3px;width:100%}.mw-parser-output .subnavbox_group{background:#e6e6ff;padding:0 10px}@media screen{html.skin-theme-clientpref-night .mw-parser-output .navbox>tbody>tr:first-child>th{background:var(--background-color-interactive)!important}html.skin-theme-clientpref-night .mw-parser-output .navbox th{color:var(--color-base)!important}html.skin-theme-clientpref-night .mw-parser-output .navbox_abovebelow,html.skin-theme-clientpref-night .mw-parser-output .navbox_group{background:var(--background-color-interactive-subtle)!important}html.skin-theme-clientpref-night .mw-parser-output .subnavbox_group{background:var(--background-color-neutral-subtle)!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbox>tbody>tr:first-child>th{background:var(--background-color-interactive)!important}html.skin-theme-clientpref-os .mw-parser-output .navbox th{color:var(--color-base)!important}html.skin-theme-clientpref-os .mw-parser-output .navbox_abovebelow,html.skin-theme-clientpref-os .mw-parser-output .navbox_group{background:var(--background-color-interactive-subtle)!important}html.skin-theme-clientpref-os .mw-parser-output .subnavbox_group{background:var(--background-color-neutral-subtle)!important}}</style><table class="navbox mw-collapsible mw-collapsed noprint metadata" id="navbox-Stereochimica"><tbody><tr><th colspan="3"><div class="navbox_navbar"><div class="noprint plainlinks" style="background-color:transparent; padding:0; font-size:xx-small; color:var(--color-base, #000000); white-space:nowrap;"><a href="/wiki/Template:Stereochimica" title="Template:Stereochimica"><span title="Vai alla pagina del template">V</span></a> · <a href="/w/index.php?title=Discussioni_template:Stereochimica&action=edit&redlink=1" class="new" title="Discussioni template:Stereochimica (la pagina non esiste)"><span title="Discuti del template">D</span></a> · <a class="external text" href="https://it.wikipedia.org/w/index.php?title=Template:Stereochimica&action=edit"><span title="Modifica il template. Usa l'anteprima prima di salvare">M</span></a></div></div><span class="navbox_title"><a href="/wiki/Stereochimica" title="Stereochimica">Stereochimica</a></span></th></tr><tr><th colspan="1" class="navbox_group"><a href="/wiki/Isomeria" title="Isomeria">Isomeria</a></th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Stereoisomero" title="Stereoisomero">Stereoisomero</a><b> ·</b> <a href="/wiki/Enantiomero" title="Enantiomero">Enantiomero</a><b> ·</b> <a href="/wiki/Diastereoisomero" title="Diastereoisomero">Diastereoisomero</a><b> ·</b> <a href="/wiki/Epimero" title="Epimero">Epimero</a><b> ·</b> <a href="/wiki/Composto_meso" title="Composto meso">Composto meso</a></td><td rowspan="5" class="navbox_image"><span typeof="mw:File"><a href="/wiki/File:Chirality_with_hands.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Chirality_with_hands.svg/175px-Chirality_with_hands.svg.png" decoding="async" width="175" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Chirality_with_hands.svg/263px-Chirality_with_hands.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Chirality_with_hands.svg/350px-Chirality_with_hands.svg.png 2x" data-file-width="765" data-file-height="519" /></a></span></td></tr><tr><th colspan="1" class="navbox_group"><a href="/wiki/Chiralit%C3%A0_(chimica)" title="Chiralità (chimica)">Chiralità</a></th><td colspan="1" class="navbox_list navbox_even"><a href="/wiki/Elemento_stereogenico" title="Elemento stereogenico">Elemento stereogenico</a><b> ·</b> <a href="/w/index.php?title=Chiralit%C3%A0_planare&action=edit&redlink=1" class="new" title="Chiralità planare (la pagina non esiste)">Chiralità planare</a><b> ·</b> <a href="/w/index.php?title=Ligando_chirale&action=edit&redlink=1" class="new" title="Ligando chirale (la pagina non esiste)">Ligando chirale</a><b> ·</b> <a href="/w/index.php?title=Chiralit%C3%A0_assiale&action=edit&redlink=1" class="new" title="Chiralità assiale (la pagina non esiste)">Chiralità assiale</a><b> ·</b> <a href="/wiki/Chiralit%C3%A0_inerente" title="Chiralità inerente">Chiralità inerente</a><b> ·</b> <a href="/wiki/Prochiralit%C3%A0" title="Prochiralità">Prochiralità</a><b> ·</b> <a href="/wiki/Omochiralit%C3%A0" title="Omochiralità">Omochiralità</a><b> ·</b> <a href="/wiki/Racemo_(chimica)" title="Racemo (chimica)">Racemo</a><b> ·</b> <a href="/wiki/Anomeria" title="Anomeria">Anomeria</a> <b> ·</b></td></tr><tr><th colspan="1" class="navbox_group">Sintesi</th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Stereospecificit%C3%A0" title="Stereospecificità">Stereospecificità</a><b> ·</b> <a class="mw-selflink selflink">Stereoselettività</a><b> ·</b> <a href="/wiki/Eccesso_enantiomerico" title="Eccesso enantiomerico">Eccesso enantiomerico</a><b> ·</b> <a href="/w/index.php?title=Eccesso_diastereoisomerico&action=edit&redlink=1" class="new" title="Eccesso diastereoisomerico (la pagina non esiste)">Eccesso diastereoisomerico</a></td></tr><tr><th colspan="1" class="navbox_group">Analisi</th><td colspan="1" class="navbox_list navbox_even"><a href="/wiki/Potere_rotatorio" title="Potere rotatorio">Potere rotatorio</a><b> ·</b> <a href="/w/index.php?title=Risoluzione_chirale&action=edit&redlink=1" class="new" title="Risoluzione chirale (la pagina non esiste)">Risoluzione chirale</a><b> ·</b> <a href="/wiki/Dicroismo_circolare" title="Dicroismo circolare">Dicroismo circolare</a></td></tr><tr><th colspan="1" class="navbox_group">Reazioni</th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Sintesi_asimmetrica" title="Sintesi asimmetrica">Sintesi asimmetrica</a><b> ·</b> <a href="/wiki/Ausiliario_chirale" title="Ausiliario chirale">Ausiliario chirale</a><b> ·</b> <a href="/wiki/Organocatalisi" title="Organocatalisi">Organocatalisi</a><b> ·</b> <a href="/wiki/Biocatalisi" title="Biocatalisi">Biocatalisi</a></td></tr></tbody></table> <style data-mw-deduplicate="TemplateStyles:r140554510">.mw-parser-output .CdA{border:1px solid #aaa;width:100%;margin:auto;font-size:90%;padding:2px}.mw-parser-output .CdA th{background-color:#f2f2f2;font-weight:bold;width:20%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .CdA{border-color:#54595D}html.skin-theme-clientpref-night .mw-parser-output .CdA th{background-color:#202122}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .CdA{border-color:#54595D}html.skin-theme-clientpref-os .mw-parser-output .CdA th{background-color:#202122}}</style><table class="CdA"><tbody><tr><th><a href="/wiki/Aiuto:Controllo_di_autorit%C3%A0" title="Aiuto:Controllo di autorità">Controllo di autorità</a></th><td><a href="/wiki/Gemeinsame_Normdatei" title="Gemeinsame Normdatei">GND</a> <span class="uid">(<span style="font-weight:bolder; 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