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donazione</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Speciale:CreaUtenza&returnto=Isocianuri" title="Si consiglia di registrarsi e di effettuare l'accesso, anche se non è obbligatorio" class=""><span>registrati</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Speciale:Entra&returnto=Isocianuri" title="Si consiglia di effettuare l'accesso, anche se non è obbligatorio [o]" accesskey="o" class=""><span>entra</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Altre opzioni" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" 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class="vector-menu-heading"> Pagine per utenti anonimi <a href="/wiki/Aiuto:Benvenuto" aria-label="Ulteriori informazioni sulla contribuzione"><span>ulteriori informazioni</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Speciale:MieiContributi" title="Un elenco delle modifiche fatte da questo indirizzo IP [y]" accesskey="y"><span>contributi</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Speciale:MieDiscussioni" title="Discussioni sulle modifiche fatte da questo indirizzo IP [n]" accesskey="n"><span>discussioni</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Sito"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Indice" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Indice</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">sposta nella barra laterale</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">nascondi</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">Inizio</div> </a> </li> <li id="toc-Nomenclatura" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Nomenclatura"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Nomenclatura</span> </div> </a> <ul id="toc-Nomenclatura-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Proprietà" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Proprietà"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Proprietà</span> </div> </a> <button aria-controls="toc-Proprietà-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Attiva/disattiva la sottosezione Proprietà</span> </button> <ul id="toc-Proprietà-sublist" class="vector-toc-list"> <li id="toc-Odore_degli_isocianuri" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Odore_degli_isocianuri"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Odore degli isocianuri</span> </div> </a> <ul id="toc-Odore_degli_isocianuri-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Sintesi" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Sintesi"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Sintesi</span> </div> </a> <ul id="toc-Sintesi-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reattività" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reattività"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Reattività</span> </div> </a> <ul id="toc-Reattività-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Isocianuri_di_origine_naturale" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Isocianuri_di_origine_naturale"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Isocianuri di origine naturale</span> </div> </a> <ul id="toc-Isocianuri_di_origine_naturale-sublist" class="vector-toc-list"> </ul> </li> <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">6</span> <span>Note</span> </div> </a> <ul id="toc-Note-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">7</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">8</span> <span>Altri progetti</span> </div> </a> <ul id="toc-Altri_progetti-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Collegamenti_esterni" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Collegamenti_esterni"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Collegamenti esterni</span> </div> </a> <ul id="toc-Collegamenti_esterni-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">Isocianuri</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 30 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-30" 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">30 lingue</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D9%8A%D8%B2%D9%88%D8%B3%D9%8A%D8%A7%D9%86%D9%8A%D8%AF" title="إيزوسيانيد - arabo" lang="ar" hreflang="ar" data-title="إيزوسيانيد" data-language-autonym="العربية" data-language-local-name="arabo" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%86%D0%B7%D0%B0%D1%86%D1%8B%D1%8F%D0%BD%D1%96%D0%B4%D1%8B" title="Ізацыяніды - bielorusso" lang="be" hreflang="be" data-title="Ізацыяніды" data-language-autonym="Беларуская" data-language-local-name="bielorusso" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Isocianur" title="Isocianur - catalano" lang="ca" hreflang="ca" data-title="Isocianur" 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/Isokyanidy" title="Isokyanidy - ceco" lang="cs" hreflang="cs" data-title="Isokyanidy" data-language-autonym="Čeština" data-language-local-name="ceco" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Isocyanid" title="Isocyanid - danese" lang="da" hreflang="da" data-title="Isocyanid" data-language-autonym="Dansk" data-language-local-name="danese" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Isonitrile" title="Isonitrile - tedesco" lang="de" hreflang="de" data-title="Isonitrile" 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/Isocyanide" title="Isocyanide - inglese" lang="en" hreflang="en" data-title="Isocyanide" data-language-autonym="English" data-language-local-name="inglese" 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/Izonitrilo" title="Izonitrilo - esperanto" lang="eo" hreflang="eo" data-title="Izonitrilo" data-language-autonym="Esperanto" data-language-local-name="esperanto" 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/Isocianuro" title="Isocianuro - spagnolo" lang="es" hreflang="es" data-title="Isocianuro" data-language-autonym="Español" data-language-local-name="spagnolo" 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/Isozianuro" title="Isozianuro - basco" lang="eu" hreflang="eu" data-title="Isozianuro" data-language-autonym="Euskara" data-language-local-name="basco" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%DB%8C%D8%B2%D9%88%D8%B3%DB%8C%D8%A7%D9%86%DB%8C%D8%AF" title="ایزوسیانید - persiano" lang="fa" hreflang="fa" data-title="ایزوسیانید" data-language-autonym="فارسی" data-language-local-name="persiano" 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/Isosyanidit" title="Isosyanidit - finlandese" lang="fi" hreflang="fi" data-title="Isosyanidit" data-language-autonym="Suomi" data-language-local-name="finlandese" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Isonitrile" title="Isonitrile - francese" lang="fr" hreflang="fr" data-title="Isonitrile" data-language-autonym="Français" data-language-local-name="francese" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Izocijanidi" title="Izocijanidi - croato" lang="hr" hreflang="hr" data-title="Izocijanidi" data-language-autonym="Hrvatski" data-language-local-name="croato" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Isosianida" title="Isosianida - indonesiano" lang="id" hreflang="id" data-title="Isosianida" data-language-autonym="Bahasa Indonesia" data-language-local-name="indonesiano" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A4%E3%82%BD%E3%82%B7%E3%82%A2%E3%83%8B%E3%83%89" title="イソシアニド - giapponese" lang="ja" hreflang="ja" data-title="イソシアニド" 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-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%98%D0%B7%D0%BE%D0%BD%D0%B8%D1%82%D1%80%D0%B8%D0%BB%D0%B4%D0%B5%D1%80" title="Изонитрилдер - kirghiso" lang="ky" hreflang="ky" data-title="Изонитрилдер" data-language-autonym="Кыргызча" data-language-local-name="kirghiso" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Isocyanide" title="Isocyanide - olandese" lang="nl" hreflang="nl" data-title="Isocyanide" 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/Isocianeto" title="Isocianeto - portoghese" lang="pt" hreflang="pt" data-title="Isocianeto" 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/Izocianur%C4%83" title="Izocianură - rumeno" lang="ro" hreflang="ro" data-title="Izocianură" 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%98%D0%B7%D0%BE%D0%BD%D0%B8%D1%82%D1%80%D0%B8%D0%BB%D1%8B" title="Изонитрилы - russo" lang="ru" hreflang="ru" data-title="Изонитрилы" 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/Izocijanid" title="Izocijanid - serbo-croato" lang="sh" hreflang="sh" data-title="Izocijanid" 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/Izocijanid" title="Izocijanid - serbo" lang="sr" hreflang="sr" data-title="Izocijanid" 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-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Isocyanid" title="Isocyanid - svedese" lang="sv" hreflang="sv" data-title="Isocyanid" data-language-autonym="Svenska" data-language-local-name="svedese" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%98%D0%B7%D0%BE%D0%BD%D0%B8%D1%82%D1%80%D0%B8%D0%BB%D2%B3%D0%BE" title="Изонитрилҳо - tagico" lang="tg" hreflang="tg" data-title="Изонитрилҳо" data-language-autonym="Тоҷикӣ" data-language-local-name="tagico" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/%C4%B0zonitril" title="İzonitril - turco" lang="tr" hreflang="tr" data-title="İzonitril" data-language-autonym="Türkçe" data-language-local-name="turco" 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%86%D0%B7%D0%BE%D0%BD%D1%96%D1%82%D1%80%D0%B8%D0%BB%D0%B8" title="Ізонітрили - ucraino" lang="uk" hreflang="uk" data-title="Ізонітрили" data-language-autonym="Українська" data-language-local-name="ucraino" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Izonitrillar" title="Izonitrillar - uzbeco" lang="uz" hreflang="uz" data-title="Izonitrillar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="uzbeco" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%BC%82%E8%85%88" title="异腈 - cinese" lang="zh" hreflang="zh" data-title="异腈" data-language-autonym="中文" data-language-local-name="cinese" class="interlanguage-link-target"><span>中文</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%83%A9" title="胩 - cantonese" lang="yue" hreflang="yue" data-title="胩" data-language-autonym="粵語" data-language-local-name="cantonese" class="interlanguage-link-target"><span>粵語</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/Q421897#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/Isocianuri" title="Vedi la voce [c]" accesskey="c"><span>Voce</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Discussione:Isocianuri" rel="discussion" title="Vedi le discussioni relative a questa pagina [t]" accesskey="t"><span>Discussione</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-variants-dropdown" 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class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Isocianuri&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=Isocianuri&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=Isocianuri&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" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " 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</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"><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Isocyanide_structural_formulae.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Isocyanide_structural_formulae.png/150px-Isocyanide_structural_formulae.png" decoding="async" width="150" height="58" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Isocyanide_structural_formulae.png/225px-Isocyanide_structural_formulae.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/49/Isocyanide_structural_formulae.png/300px-Isocyanide_structural_formulae.png 2x" data-file-width="1717" data-file-height="663" /></a><figcaption>Struttura di un generico isocianuro</figcaption></figure> <p>Gli <b>isocianuri</b> (conosciuti anche con le vecchie denominazioni di <b>isonitrili</b> o <b>carbilammine</b>) sono <a href="/wiki/Composti_organici" class="mw-redirect" title="Composti organici">composti organici</a> contenenti il <a href="/wiki/Gruppo_funzionale" title="Gruppo funzionale">gruppo funzionale</a> -N≡C. Il prefisso <i>iso</i> deriva dal fatto che sono isomeri dei corrispondenti cianuri organici, -C≡N, detti <a href="/wiki/Nitrili" title="Nitrili">nitrili</a>.<sup id="cite_ref-isocyanides_1-0" class="reference"><a href="#cite_note-isocyanides-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Negli isocianuri il residuo organico è connesso all'atomo di <a href="/wiki/Azoto" title="Azoto">azoto</a>, non al <a href="/wiki/Carbonio" title="Carbonio">carbonio</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclatura">Nomenclatura</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isocianuri&veaction=edit&section=1" title="Modifica la sezione Nomenclatura" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Isocianuri&action=edit&section=1" title="Edit section's source code: Nomenclatura"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nella nomenclatura <a href="/wiki/Unione_internazionale_di_chimica_pura_e_applicata" title="Unione internazionale di chimica pura e applicata">IUPAC</a> per i cianuri organici (R-C≡N) si usa in genere il <a href="/wiki/Suffisso" title="Suffisso">suffisso</a> <i>nitrile</i>, mentre per gli isocianuri si usa il <a href="/wiki/Prefisso" title="Prefisso">prefisso</a> <i>isociano</i>. Il termine <i>carbilammina</i>, ancora usato, non è in accordo con la nomenclatura sistematica, dato che una <a href="/wiki/Ammina" class="mw-redirect" title="Ammina">ammina</a> deve avere tre legami singoli, mentre l'isocianuro ha un legame semplice e un legame multiplo. </p> <div class="mw-heading mw-heading2"><h2 id="Proprietà"><span id="Propriet.C3.A0"></span>Proprietà</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isocianuri&veaction=edit&section=2" title="Modifica la sezione Proprietà" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Isocianuri&action=edit&section=2" title="Edit section's source code: Proprietà"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Isocyanide_resonance.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Isocyanide_resonance.svg/330px-Isocyanide_resonance.svg.png" decoding="async" width="330" height="49" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Isocyanide_resonance.svg/495px-Isocyanide_resonance.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Isocyanide_resonance.svg/660px-Isocyanide_resonance.svg.png 2x" data-file-width="367" data-file-height="55" /></a><figcaption>Strutture di <a href="/wiki/Risonanza_(chimica)" title="Risonanza (chimica)">risonanza</a> di un generico isocianuro</figcaption></figure> <p>La molecola di un isocianuro è un <a href="/wiki/Risonanza_(chimica)" title="Risonanza (chimica)">ibrido di risonanza</a> tra due forme limite, una con un <a href="/wiki/Triplo_legame" title="Triplo legame">triplo legame</a> tra un azoto formalmente positivo e un carbonio formalmente negativo, e un'altra con un <a href="/wiki/Doppio_legame" title="Doppio legame">doppio legame</a> tra N e C, che lascia quest'ultimo con solo 6 elettroni di valenza (forma <a href="/wiki/Carbene" title="Carbene">carbenica</a>). La prima, con <a href="/wiki/Regola_dell%27ottetto" title="Regola dell'ottetto">ottetti</a> completi, è la più importante, anche se contiene una separazione di carica energeticamente sfavorevole (N più elettronegativo di C),<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> e ha maggior peso nel rappresentare l'ibrido di risonanza rispetto alla seconda forma con C senza ottetto. </p><p>Gli isocianuri sono localmente <a href="/wiki/Isoelettronico" title="Isoelettronico">isoelettronici</a> con il monossido di carbonio <sup>(–)</sup><b>:</b>C≡O<b>:</b><sup>(+)</sup>, oltre che con i nitrili. Gli atomi N e C sono ibridati <i>sp</i> e, di conseguenza, la struttura C–N–C(R<sub>3</sub>) è lineare (R rappresenta idrogeno o un qualsiasi gruppo organico) e, salvo particolari ingombri sterici dei gruppi R, gli angoli sono molto vicini a 180°;<sup id="cite_ref-Kessler1950_3-0" class="reference"><a href="#cite_note-Kessler1950-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> la lunghezza del triplo legame nell'<a href="/w/index.php?title=Isocianuro_di_metile&action=edit&redlink=1" class="new" title="Isocianuro di metile (la pagina non esiste)">isocianuro di metile</a> è di 115,8 <a href="/wiki/Metro" title="Metro">pm</a>,<sup id="cite_ref-Kessler1950_3-1" class="reference"><a href="#cite_note-Kessler1950-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> praticamente uguale a quella in <a href="/wiki/Acido_cianidrico" title="Acido cianidrico">HC≡N</a> e <a href="/wiki/Acetonitrile" title="Acetonitrile">CH<sub>3</sub>C≡N</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Gli isocianuri sono anche dei <a href="/wiki/Ligando" title="Ligando">leganti</a> per centri metallici, di cui si conoscono diversi <a href="/wiki/Complesso_(chimica)" title="Complesso (chimica)">complessi</a>.<sup id="cite_ref-:32_5-0" class="reference"><a href="#cite_note-:32-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Come il monossido di carbonio, anche gli isocianuri possono legarsi ad <a href="/wiki/Elementi_di_transizione" title="Elementi di transizione">atomi metallici di transizione</a> dando complessi <a href="/wiki/Chimica_metallorganica" title="Chimica metallorganica">organometallici</a> del tipo M(C≡N-R)<sub>n</sub> con M in <a href="/wiki/Stato_di_ossidazione" title="Stato di ossidazione">stato di ossidazione</a> anche nullo, come in Cr(C≡N-C<sub>6</sub>H<sub>5</sub>)<sub>6</sub>, un composto cristallino rosso, stabile all'aria e facilmente solubile in <a href="/wiki/Benzene" title="Benzene">benzene</a>.<sup id="cite_ref-:0_6-0" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Questi complessi sono analoghi ai <a href="/wiki/Metallocarbonile" title="Metallocarbonile">metallocarbonili</a> e, come questi ultimi, generalmente rispettano la <a href="/wiki/Regola_dei_18_elettroni" title="Regola dei 18 elettroni">regola dei 18 elettroni</a> di valenza per il metallo M. A differenza di CO, gli isocianuri possono dare complessi stabili anche con ioni metallici positivi (2+, anche 3+). I leganti C≡N-R hanno minore capacità accettrice <a href="/wiki/Legame_%CF%80" title="Legame π">pi-greco</a> e maggiore capacità donatrice <a href="/wiki/Legame_%CF%83" title="Legame σ">sigma</a> rispetto al CO,<sup id="cite_ref-:3_7-0" class="reference"><a href="#cite_note-:3-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> e ciò favorisce il legame donatore-accettore (tipico nei complessi) con ioni metallici positivi. I leganti isocianuro permettono l'ottenimento, ad esempio, di [Fe(C≡N-R)<sub>6</sub>]<sup>2+</sup> e [Mn(C≡N-R)<sub>6</sub>]<sup>2+</sup>,<sup id="cite_ref-:0_6-1" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> dei quali non esistono i metallocarbonili analoghi. A questo riguardo, il legante isocianuro si pone approssimativamente a metà strada tra CO e lo <a href="/wiki/Cianuro" title="Cianuro">ione cianuro</a> (<sup>-</sup> C≡N), quest'ultimo essendo donatore migliore,<sup id="cite_ref-:3_7-1" class="reference"><a href="#cite_note-:3-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> che permette di ottenere cianocomplessi anche di M<sup>IV</sup> e M<sup>V</sup>.<sup id="cite_ref-:2_8-0" class="reference"><a href="#cite_note-:2-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Odore_degli_isocianuri">Odore degli isocianuri</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isocianuri&veaction=edit&section=3" title="Modifica la sezione Odore degli isocianuri" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Isocianuri&action=edit&section=3" title="Edit section's source code: Odore degli isocianuri"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Il loro odore sgradevole è leggendario. Il chimico tedesco Lieke scrisse già nel 1859:<sup id="cite_ref-Lieke_9-0" class="reference"><a href="#cite_note-Lieke-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><i>Possiede un odore penetrante, estremamente sgradevole; basta aprire un recipiente di allil [iso]cianuro per appestare l'aria di una stanza per parecchi giorni.</i></dd></dl> <p>Ai tempi di Lieke la differenza tra cianuri e isocianuri non era ben compresa. </p><p>Il chimico tedesco Ivar Karl Ugi scrisse: </p> <dl><dd><i>Lo sviluppo della chimica degli isocianuri ha probabilmente sofferto ... a causa dell'odore caratteristico degli isocianuri volatili, che Hofmann e Gauthier hanno descritto come "molto particolare, quasi insopportabile", "orribile" ed "estremamente angoscioso". È certo che molti potenziali ricercatori in questo campo sono stati dissuasi dall'odore</i>.<sup id="cite_ref-:1_10-0" class="reference"><a href="#cite_note-:1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></dd></dl> <p>Gli isocianuri sono stati studiati per un possibile uso come <a href="/wiki/Arma_non_letale" title="Arma non letale">arma non letale</a>.<sup id="cite_ref-Pirrung_11-0" class="reference"><a href="#cite_note-Pirrung-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Esistono anche isocianuri che non hanno odore disgustoso.<sup id="cite_ref-Pirrung_11-1" class="reference"><a href="#cite_note-Pirrung-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Sintesi">Sintesi</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isocianuri&veaction=edit&section=4" title="Modifica la sezione Sintesi" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Isocianuri&action=edit&section=4" title="Edit section's source code: Sintesi"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Il primo isocianuro, l'isocianuro di <a href="/wiki/Allile" title="Allile">allile</a>, fu preparato nel 1859 dal chimico tedesco Lieke facendo reagire <a href="/wiki/Ioduro_di_allile" class="mw-redirect" title="Ioduro di allile">ioduro di allile</a> e <a href="/wiki/Cianuro_di_argento" class="mw-redirect" title="Cianuro di argento">cianuro di argento</a>.<sup id="cite_ref-Lieke_9-1" class="reference"><a href="#cite_note-Lieke-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Normalmente per <a href="/wiki/Alchilazione" title="Alchilazione">alchilazione</a> di un cianuro di un metallo alcalino si ottiene il nitrile, ma il catione Ag<sup>+</sup> è un <a href="/wiki/Teoria_HSAB" title="Teoria HSAB">acido <i>soft</i></a> e protegge il carbonio terminale del cianuro. In genere gli isocianuri sono sintetizzati per reazione di <a href="/wiki/Ammine" title="Ammine">ammine</a> primarie con <a href="/wiki/Diclorocarbene" title="Diclorocarbene">diclorocarbene</a>, o per disidratazione di una <a href="/wiki/Formammide" title="Formammide">formammide</a> con <a href="/wiki/Ossicloruro_di_fosforo" title="Ossicloruro di fosforo">ossicloruro di fosforo</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>RNH<sub>2</sub> + <b>:</b>CCl<sub>2</sub> + 2 NaOH → RNC + 2NaCl + 2H<sub>2</sub>O</dd> <dd>RNHC(O)H + POCl<sub>3</sub> → RNC + "PO<sub>2</sub>Cl" + 2HCl</dd></dl> <p>La <b>sintesi di Hofmann degli isocianuri</b> è un <a href="/wiki/Saggio_chimico" title="Saggio chimico">saggio chimico</a> per le <a href="/wiki/Ammine_primarie" class="mw-redirect" title="Ammine primarie">ammine primarie</a>, basato sulla loro reazione con <a href="/wiki/Idrossido_di_potassio" title="Idrossido di potassio">idrossido di potassio</a> e <a href="/wiki/Cloroformio" title="Cloroformio">cloroformio</a>, che fungono da precursori di <a href="/wiki/Diclorocarbene" title="Diclorocarbene">diclorocarbene</a>. Se è presente una ammina primaria si sviluppa il terribile odore degli isocianuri. </p><p>Un'altra sintesi degli isocianuri è la reazione di <a href="/w/index.php?title=Composti_organolitio&action=edit&redlink=1" class="new" title="Composti organolitio (la pagina non esiste)">composti organolitio</a> con <a href="/wiki/Ossazolo" title="Ossazolo">ossazoli</a> e <a href="/wiki/Benzossazolo" title="Benzossazolo">benzossazoli</a>:<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:IsonitrileOxazoleSynthesis.png" class="mw-file-description" title="Sintesi di isonitrili tramite ossazoli"><img alt="Sintesi di isonitrili tramite ossazoli" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/IsonitrileOxazoleSynthesis.png/400px-IsonitrileOxazoleSynthesis.png" decoding="async" width="400" height="287" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/IsonitrileOxazoleSynthesis.png/600px-IsonitrileOxazoleSynthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/IsonitrileOxazoleSynthesis.png/800px-IsonitrileOxazoleSynthesis.png 2x" data-file-width="1072" data-file-height="769" /></a><figcaption>Sintesi di isonitrili tramite ossazoli</figcaption></figure> <p>Il benzossazolo viene deprotonato in posizione 2 dal <a href="/wiki/N-butillitio" title="N-butillitio">n-butillitio</a>. Il composto litiato è in equilibrio con il 2-isocianofenolato, che viene catturato da un <a href="/wiki/Elettrofilo" title="Elettrofilo">elettrofilo</a> come un <a href="/wiki/Cloruro_acilico" class="mw-redirect" title="Cloruro acilico">cloruro acilico</a>. Nell'esempio illustrato, l'isocianuro che si forma è anche un <a href="/wiki/Estere" class="mw-redirect" title="Estere">estere</a>, e ha odore di <a href="/wiki/Ciliegia" title="Ciliegia">ciliegia</a> anziché il caratteristico odore degli isocianuri. </p><p>Un'altra sintesi degli isocianuri prevede la condensazione di una ammina con acido formico, e successiva disidratazione della formammide risultante. Si può usare <a href="/wiki/Fosgene" title="Fosgene">fosgene</a> (o un precursore come il <a href="/wiki/Difosg%C3%A8ne" title="Difosgène">difosgène</a>) assieme alla formammide per ottenere isocianuri. </p><p>Nel 2022 è stata sviluppata una sintesi degli isonitrili basata sull'approccio utilizzato da Ugi. <sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> La reazione vede l'impiego della meccanochimica come fonte di energia per l'attivazione del processo, e l'impiego di reagenti meno tossici rispetto alla sintesi tradizionale.<sup id="cite_ref-:1_10-1" class="reference"><a href="#cite_note-:1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Si sviluppa a partire da una formammide aromatica o alifatica che, in ambiente basico per trietilammina e carbonato di sodio, e in presenza di un agente disidratante come il tosil cloruro, va incontro ad un processo di disidratazione che porta alla formazione dell'isonitrile corrispondente in elevate rese. Parallelamente al miglioramento del processo di sintesi, questa procedura vanta un innovativo metodo di purificazione del prodotto, attuato in fase solida per aggiunta di un quantitativo stechiometrico di acqua. </p> <div class="mw-heading mw-heading2"><h2 id="Reattività"><span id="Reattivit.C3.A0"></span>Reattività</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isocianuri&veaction=edit&section=5" title="Modifica la sezione Reattività" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Isocianuri&action=edit&section=5" title="Edit section's source code: Reattività"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Gli isocianuri sono stabili in presenza di basi forti (si preparano spesso in condizioni fortemente basiche), a differenza dei nitrili, ma sono sensibili agli acidi. In presenza di acidi acquosi si idrolizzano alle corrispondenti formammidi. Alcuni isocianuri possono polimerizzare in presenza di acidi. L'idrolisi acida è un modo pratico per eliminare gli isocianuri e il loro insopportabile odore. </p><p>Gli isocianuri si usano in due <a href="/wiki/Reazione_multicomponente" title="Reazione multicomponente">reazioni multicomponente</a> utili in <a href="/wiki/Chimica_organica" title="Chimica organica">chimica organica</a>: la <a href="/wiki/Reazione_di_Ugi" title="Reazione di Ugi">reazione di Ugi</a> e la <a href="/w/index.php?title=Reazione_di_Passerini&action=edit&redlink=1" class="new" title="Reazione di Passerini (la pagina non esiste)">reazione di Passerini</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Isocianuri_di_origine_naturale">Isocianuri di origine naturale</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isocianuri&veaction=edit&section=6" title="Modifica la sezione Isocianuri di origine naturale" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Isocianuri&action=edit&section=6" title="Edit section's source code: Isocianuri di origine naturale"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Il gruppo isocianuro è presente in varie molecole organiche estratte da organismi viventi. Il primo esempio fu scoperto nel 1957 in un estratto della muffa <i><a href="/wiki/Penicillium_notatum" class="mw-redirect" title="Penicillium notatum">Penicillium notatum</a></i> Westling. La <a href="/wiki/Xantocillina" title="Xantocillina">xantocillina</a> fu successivamente usata come <a href="/wiki/Antibiotico" title="Antibiotico">antibiotico</a>. In seguito sono stati isolati molti altri isocianuri. La maggior parte degli isocianuri di origine marina sono <a href="/wiki/Terpeni" title="Terpeni">terpeni</a>, mentre alcuni di quelli di origine terrestre derivano da α-<a href="/wiki/Amminoacidi" class="mw-redirect" title="Amminoacidi">amminoacidi</a>.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <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=Isocianuri&veaction=edit&section=7" 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=Isocianuri&action=edit&section=7" 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 mw-references-columns"><ol class="references"> <li id="cite_note-isocyanides-1"><a href="#cite_ref-isocyanides_1-0"><b>^</b></a> <span class="reference-text"><cite class="citation web" style="font-style:normal"> IUPAC Goldbook, <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/I03270.html"><span style="font-style:italic;">Isocyanides</span></a>, su <span style="font-style:italic;">goldbook.iupac.org</span>. <small>URL consultato il 14-2-2011</small>.</cite></span> </li> <li id="cite_note-2"><a href="#cite_ref-2"><b>^</b></a> <span class="reference-text"><cite class="citation libro" style="font-style:normal"> J.B. 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Griffith, <a rel="nofollow" class="external text" href="https://linkinghub.elsevier.com/retrieve/pii/S0010854500803033"><span style="font-style:italic;">Cyanide complexes of the early transition metals (groups IVa-VIIa)</span></a>, in <span style="font-style:italic;">Coordination Chemistry Reviews</span>, vol. 17, n. 2-3, 1975-11, pp. 177–247, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1016%2FS0010-8545%2800%2980303-3">10.1016/S0010-8545(00)80303-3</a>. <small>URL consultato il 4 gennaio 2021</small>.</cite></span> </li> <li id="cite_note-Lieke-9"><span class="mw-cite-backlink"><b>^</b> <sup><i><a href="#cite_ref-Lieke_9-0">a</a></i></sup> <sup><i><a href="#cite_ref-Lieke_9-1">b</a></i></sup></span> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> W. Lieke, <a rel="nofollow" class="external text" href="http://books.google.com/?id=NYs8AAAAIAAJ&pg=RA1-PA319&dq=Cyanallyl++%22Es+besitzt+einen+penetranten%22"><span style="font-style:italic;">Ueber das Cyanallyl</span></a>, in <span style="font-style:italic;">Justus Liebigs Annalen der Chemie</span>, vol. 112, n. 3, 1859, pp. 316-321, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1002%2Fjlac.18591120307">10.1002/jlac.18591120307</a>. <small>URL consultato il 15-2-2011</small>.</cite></span> </li> <li id="cite_note-:1-10"><span class="mw-cite-backlink"><b>^</b> <sup><i><a href="#cite_ref-:1_10-0">a</a></i></sup> <sup><i><a href="#cite_ref-:1_10-1">b</a></i></sup></span> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> I. Ugi, U. Fetzer, U. Eholzer, H. Knupfer, K. Offermann, <a rel="nofollow" class="external text" href="https://oadoi.org/10.1002/anie.196504721"><span style="font-style:italic;">Isonitrile syntheses</span></a>, in <span style="font-style:italic;">Angew. Chem., Int. Ed. Eng.</span>, vol. 4, n. 6, 1965, pp. 472-484, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1002%2Fanie.196504721">10.1002/anie.196504721</a>. <small>URL consultato il 15-2-2011</small>.</cite></span> </li> <li id="cite_note-Pirrung-11"><span class="mw-cite-backlink"><b>^</b> <sup><i><a href="#cite_ref-Pirrung_11-0">a</a></i></sup> <sup><i><a href="#cite_ref-Pirrung_11-1">b</a></i></sup></span> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> M. C. Pirrung, S. Ghorai, T. R. Ibarra-Rivera, <span style="font-style:italic;">Multicomponent reactions of convertible isonitriles</span>, in <span style="font-style:italic;">J. 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Scheuer, <a rel="nofollow" class="external text" href="https://oadoi.org/10.1021/ar00022a001"><span style="font-style:italic;">Isocyanides and cyanides as natural products</span></a>, in <span style="font-style:italic;">Acc. Chem. Res.</span>, vol. 25, n. 10, 1992, pp. 433-439, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1021%2Far00022a001">10.1021/ar00022a001</a>. <small>URL consultato il 15-2-2011</small>.</cite></span> </li> </ol></div> <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=Isocianuri&veaction=edit&section=8" 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=Isocianuri&action=edit&section=8" 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/Nitrili" title="Nitrili">Nitrili</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=Isocianuri&veaction=edit&section=9" 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=Isocianuri&action=edit&section=9" 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:Isocyanides"><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Isocyanides?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:Isocyanides?uselang=it">Isocianuri</a></span></b></li></ul> <div class="mw-heading mw-heading2"><h2 id="Collegamenti_esterni">Collegamenti esterni</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isocianuri&veaction=edit&section=10" title="Modifica la sezione Collegamenti esterni" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Isocianuri&action=edit&section=10" title="Edit section's source code: Collegamenti esterni"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li class="mw-empty-elt"></li> <li><cite id="CITEREFSapere.it" class="citation web" style="font-style:normal"> <a rel="nofollow" class="external text" href="https://www.sapere.it/enciclopedia/isonitrile.html"><span style="font-style:italic;">isonitrile</span></a>, su <span style="font-style:italic;">sapere.it</span>, <a href="/wiki/De_Agostini" title="De Agostini">De Agostini</a>.</cite> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q421897#P6706" title="Modifica su Wikidata"><img alt="Modifica su Wikidata" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/10px-Blue_pencil.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/15px-Blue_pencil.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/20px-Blue_pencil.svg.png 2x" data-file-width="600" data-file-height="600" /></a></span></li> <li><cite id="CITEREFBritannica.com" class="citation web" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) <a rel="nofollow" class="external text" href="https://www.britannica.com/science/isocyanide"><span style="font-style:italic;">isocyanide</span></a>, su <span style="font-style:italic;"><a href="/wiki/Enciclopedia_Britannica" title="Enciclopedia Britannica">Enciclopedia Britannica</a></span>, Encyclopædia Britannica, Inc.</cite> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q421897#P1417" title="Modifica su Wikidata"><img alt="Modifica su Wikidata" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/10px-Blue_pencil.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/15px-Blue_pencil.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/20px-Blue_pencil.svg.png 2x" data-file-width="600" data-file-height="600" /></a></span></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-Sistematica_organica"><tbody><tr><th colspan="2" style="background:azzurro;"><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:Sistematica_organica" title="Template:Sistematica organica"><span title="Vai alla pagina del template">V</span></a> · <a href="/w/index.php?title=Discussioni_template:Sistematica_organica&action=edit&redlink=1" class="new" title="Discussioni template:Sistematica organica (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:Sistematica_organica&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/Sistematica_organica" title="Sistematica organica">Sistematica organica</a></span></th></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;"><a href="/wiki/Composti_alifatici" title="Composti alifatici">Composti alifatici</a></th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Acetali" title="Acetali">Acetali</a> · <a href="/wiki/Acidi_carbossilici" title="Acidi carbossilici">Acidi carbossilici</a> · <a href="/wiki/Alcani" title="Alcani">Alcani</a> · <a href="/wiki/Alcheni" title="Alcheni">Alcheni</a> · <a href="/wiki/Alchini" title="Alchini">Alchini</a> · <a href="/wiki/Alcoli" title="Alcoli">Alcoli</a> · <a href="/wiki/Aldeidi" title="Aldeidi">Aldeidi</a> · <a href="/wiki/Anidride" title="Anidride">Anidridi</a> · <a href="/wiki/Annuleni" title="Annuleni">Annuleni</a> · <a href="/wiki/Chetali" title="Chetali">Chetali</a> · <a href="/wiki/Chetoni" title="Chetoni">Chetoni</a> · <a href="/wiki/Cicloalcani" title="Cicloalcani">Cicloalcani</a> · <a href="/wiki/Cicloalcheni" title="Cicloalcheni">Cicloalcheni</a> · <a href="/wiki/Dioli" title="Dioli">Dioli</a> · <a href="/wiki/Enoli" title="Enoli">Enoli</a> · <a href="/wiki/Epossidi" title="Epossidi">Epossidi</a> · <a href="/wiki/Esteri" title="Esteri">Esteri</a> · <a href="/wiki/Eteri" title="Eteri">Eteri</a> · <a href="/wiki/Eteri_corona" title="Eteri corona">Eteri corona</a> · <a href="/wiki/Lattoni" title="Lattoni">Lattoni</a> · <a href="/wiki/Lattoli" title="Lattoli">Lattoli</a> · <a href="/wiki/Perossidi" title="Perossidi">Perossidi</a> · <a href="/wiki/Perossiacido" title="Perossiacido">Perossiacidi</a> · <a href="/wiki/Polieni" title="Polieni">Polieni</a> · <a href="/wiki/Polioli" title="Polioli">Polioli</a></td></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;"><a href="/wiki/Composti_aromatici" title="Composti aromatici">Composti aromatici</a></th><td colspan="1" class="navbox_list navbox_even"><a href="/w/index.php?title=Arini_(chimica)&action=edit&redlink=1" class="new" title="Arini (chimica) (la pagina non esiste)">Arini</a> · <a href="/wiki/Ciclofani" title="Ciclofani">Ciclofani</a> · <a href="/wiki/Benzene" title="Benzene">Benzene</a> · <a href="/wiki/Fenoli" title="Fenoli">Fenoli</a> · <a href="/w/index.php?title=Eterocicli_aromatici&action=edit&redlink=1" class="new" title="Eterocicli aromatici (la pagina non esiste)">Eterocicli aromatici</a></td></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;"><a href="/wiki/Azoto#Composti_dell'azoto" title="Azoto">Contenenti azoto</a></th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Alcaloidi" title="Alcaloidi">Alcaloidi</a> · <a href="/wiki/Ammonio" title="Ammonio">Ammonio</a> · <a href="/wiki/Ammidi" title="Ammidi">Ammidi</a> · <a href="/wiki/Ammine" title="Ammine">Ammine</a> · <a href="/wiki/Amminali" title="Amminali">Amminali</a> · <a href="/wiki/Azine" title="Azine">Azine</a> · <a href="/wiki/Azoturo" title="Azoturo">Azidi</a> · <a href="/wiki/Azocomposti" title="Azocomposti">Azocomposti</a> · <a href="/wiki/Azoli" title="Azoli">Azoli</a> · <a href="/wiki/Carbammati" title="Carbammati">Carbammati</a> · <a href="/wiki/Cianidrine" title="Cianidrine">Cianidrine</a> · <a href="/wiki/Diazocomposti" title="Diazocomposti">Diazocomposti</a> · <a href="/wiki/Idrazoni" title="Idrazoni">Idrazoni</a> · <a href="/wiki/Immidi" title="Immidi">Immidi</a> · <a href="/wiki/Immine" title="Immine">Immine</a> · <a href="/wiki/Isocianati" title="Isocianati">Isocianati</a> · <a class="mw-selflink selflink">Isocianuri</a> · <a href="/wiki/Isotiocianati" title="Isotiocianati">Isotiocianati</a> · <a href="/wiki/Lattami" title="Lattami">Lattami</a> · <a href="/wiki/Nitrili" title="Nitrili">Nitrili</a> · <a href="/wiki/Nitroderivati" title="Nitroderivati">Nitrocomposti</a> · <a href="/wiki/Nitrosocomposti" class="mw-redirect" title="Nitrosocomposti">Nitrosocomposti</a> · <a href="/wiki/Osazoni" title="Osazoni">Osazoni</a> · <a href="/wiki/Ossima" title="Ossima">Ossime</a></td></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;"><a href="/wiki/Zolfo#Composti_dello_zolfo" title="Zolfo">Contenenti zolfo</a></th><td colspan="1" class="navbox_list navbox_even"><a href="/wiki/Acidi_solfonici" title="Acidi solfonici">Acidi solfonici</a> · <a href="/wiki/Ditiani" title="Ditiani">Ditiani</a> · <a href="/wiki/Isotiocianati" title="Isotiocianati">Isotiocianati</a> · <a href="/wiki/Solfoni" title="Solfoni">Solfoni</a> · <a href="/wiki/Solfossidi" title="Solfossidi">Solfossidi</a> · <a href="/wiki/Tioesteri" title="Tioesteri">Tioesteri</a> · <a href="/wiki/Tioeteri" title="Tioeteri">Tioeteri</a> · <a href="/wiki/Tioli" title="Tioli">Tioli</a> · <a href="/wiki/Tioacetali" title="Tioacetali">Tioacetali</a> · <a href="/wiki/Tiochetali" title="Tiochetali">Tiochetali</a></td></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;"><a href="/wiki/Alogenuro" title="Alogenuro">Contenenti alogeni</a></th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Alogenuri_acilici" title="Alogenuri acilici">Alogenuri acilici</a> · <a href="/wiki/Alogenuri_alchilici" title="Alogenuri alchilici">Alogenuri alchilici</a></td></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;"><a href="/wiki/Silicio#Composti" title="Silicio">Contenenti silicio</a></th><td colspan="1" class="navbox_list navbox_even"><a href="/wiki/Silani" title="Silani">Silani</a> · <a href="/w/index.php?title=Sililalchini&action=edit&redlink=1" class="new" title="Sililalchini (la pagina non esiste)">Sililalchini</a> · <a href="/w/index.php?title=Sililalogenuri&action=edit&redlink=1" class="new" title="Sililalogenuri (la pagina non esiste)">Sililalogenuri</a> · <a href="/w/index.php?title=Sililidruri&action=edit&redlink=1" class="new" title="Sililidruri (la pagina non esiste)">Sililidruri</a> · <a href="/w/index.php?title=Silanoli&action=edit&redlink=1" class="new" title="Silanoli (la pagina non esiste)">Silanoli</a> · <a href="/wiki/Alcossisilani" title="Alcossisilani">Alcossisilani</a> · <a href="/wiki/Silossani" title="Silossani">Silossani</a> · <a href="/w/index.php?title=Silazani&action=edit&redlink=1" class="new" title="Silazani (la pagina non esiste)">Silazani</a></td></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;">Altro</th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Alcossido" title="Alcossido">Alcossidi</a> · <a href="/wiki/Idrocarburi" title="Idrocarburi">Idrocarburi</a> · <a href="/wiki/Stannani" title="Stannani">Stannani</a> · <a href="/wiki/Terpeni" title="Terpeni">Terpeni</a></td></tr><tr><th colspan="2" class="navbox_abovebelow">Vedi pure <i><a href="/wiki/Nomenclatura_IUPAC_dei_composti_organici" title="Nomenclatura IUPAC dei composti organici">Nomenclatura IUPAC dei composti organici</a></i></th></tr></tbody></table> <div class="noprint" style="width:100%; padding: 3px 0; display: flex; flex-wrap: wrap; row-gap: 4px; column-gap: 8px; box-sizing: border-box;"><div style="flex-grow: 1"><style data-mw-deduplicate="TemplateStyles:r140555418">.mw-parser-output .itwiki-template-occhiello{width:100%;line-height:25px;border:1px solid #CCF;background-color:#F0EEFF;box-sizing:border-box}.mw-parser-output .itwiki-template-occhiello-progetto{background-color:#FAFAFA}@media screen{html.skin-theme-clientpref-night .mw-parser-output .itwiki-template-occhiello{background-color:#202122;border-color:#54595D}html.skin-theme-clientpref-night .mw-parser-output .itwiki-template-occhiello-progetto{background-color:#282929}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .itwiki-template-occhiello{background-color:#202122;border-color:#54595D}html.skin-theme-clientpref-os .mw-parser-output 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