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異性化 - Wikipedia
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class="vector-sitenotice-container"> <div id="siteNotice"><!-- CentralNotice --></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="サイト"> <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="目次" 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">目次</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">サイドバーに移動</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">非表示</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">ページ先頭</div> </a> </li> <li id="toc-異性化の事例" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#異性化の事例"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>異性化の事例</span> </div> </a> <ul id="toc-異性化の事例-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-脚注" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#脚注"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>脚注</span> </div> </a> <button 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vector-page-titlebar"> <nav aria-label="目次" 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="目次の表示・非表示を切り替え" > <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">目次の表示・非表示を切り替え</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">異性化</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="特定の記事の別の言語版に移動します。 利用可能な言語25件" > <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-25" 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">25の言語版</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D8%B5%D8%A7%D9%88%D8%BA%D8%A9" title="アラビア語: مصاوغة" lang="ar" hreflang="ar" data-title="مصاوغة" data-language-autonym="العربية" data-language-local-name="アラビア語" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B8%E0%A6%AE%E0%A6%BE%E0%A6%A3%E0%A7%81%E0%A6%95%E0%A6%B0%E0%A6%A3" title="ベンガル語: সমাণুকরণ" lang="bn" hreflang="bn" data-title="সমাণুকরণ" data-language-autonym="বাংলা" data-language-local-name="ベンガル語" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Izomerizacija" title="ボスニア語: Izomerizacija" lang="bs" hreflang="bs" data-title="Izomerizacija" data-language-autonym="Bosanski" data-language-local-name="ボスニア語" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Isomeritzaci%C3%B3" title="カタロニア語: Isomerització" lang="ca" hreflang="ca" data-title="Isomerització" data-language-autonym="Català" data-language-local-name="カタロニア語" 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/Izomerizace" title="チェコ語: Izomerizace" lang="cs" hreflang="cs" data-title="Izomerizace" data-language-autonym="Čeština" data-language-local-name="チェコ語" 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/Isomerisierung" title="ドイツ語: Isomerisierung" lang="de" hreflang="de" data-title="Isomerisierung" data-language-autonym="Deutsch" data-language-local-name="ドイツ語" 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/Isomerization" title="英語: Isomerization" lang="en" hreflang="en" data-title="Isomerization" data-language-autonym="English" data-language-local-name="英語" 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/Isomerizaci%C3%B3n" title="スペイン語: Isomerización" lang="es" hreflang="es" data-title="Isomerización" data-language-autonym="Español" data-language-local-name="スペイン語" 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/Isomerisatsioon" title="エストニア語: Isomerisatsioon" lang="et" hreflang="et" data-title="Isomerisatsioon" data-language-autonym="Eesti" data-language-local-name="エストニア語" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%87%D9%85%D9%BE%D8%A7%D8%B1%DB%8C" title="ペルシア語: همپاری" lang="fa" hreflang="fa" data-title="همپاری" data-language-autonym="فارسی" data-language-local-name="ペルシア語" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Isomerizaci%C3%B3n" title="ガリシア語: Isomerización" lang="gl" hreflang="gl" data-title="Isomerización" data-language-autonym="Galego" data-language-local-name="ガリシア語" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%BB%D5%A6%D5%B8%D5%B4%D5%A5%D6%80%D5%A1%D6%81%D5%B8%D6%82%D5%B4" title="アルメニア語: Իզոմերացում" lang="hy" hreflang="hy" data-title="Իզոմերացում" data-language-autonym="Հայերեն" data-language-local-name="アルメニア語" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%9D%B4%EC%84%B1%EC%A7%88%EC%B2%B4%ED%99%94_%EB%B0%98%EC%9D%91" title="韓国語: 이성질체화 반응" lang="ko" hreflang="ko" data-title="이성질체화 반응" data-language-autonym="한국어" data-language-local-name="韓国語" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Pengisomeran" title="マレー語: Pengisomeran" lang="ms" hreflang="ms" data-title="Pengisomeran" data-language-autonym="Bahasa Melayu" data-language-local-name="マレー語" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Isomerisatie" title="オランダ語: Isomerisatie" lang="nl" hreflang="nl" data-title="Isomerisatie" data-language-autonym="Nederlands" data-language-local-name="オランダ語" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Izomeryzacja" title="ポーランド語: Izomeryzacja" lang="pl" hreflang="pl" data-title="Izomeryzacja" data-language-autonym="Polski" data-language-local-name="ポーランド語" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Izomerizare" title="ルーマニア語: Izomerizare" lang="ro" hreflang="ro" data-title="Izomerizare" data-language-autonym="Română" data-language-local-name="ルーマニア語" 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%BC%D0%B5%D1%80%D0%B8%D0%B7%D0%B0%D1%86%D0%B8%D1%8F" title="ロシア語: Изомеризация" lang="ru" hreflang="ru" data-title="Изомеризация" data-language-autonym="Русский" data-language-local-name="ロシア語" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Isomerization" title="シンプル英語: Isomerization" lang="en-simple" hreflang="en-simple" data-title="Isomerization" data-language-autonym="Simple English" data-language-local-name="シンプル英語" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Izomeriz%C3%A1cia" title="スロバキア語: Izomerizácia" lang="sk" hreflang="sk" data-title="Izomerizácia" data-language-autonym="Slovenčina" data-language-local-name="スロバキア語" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Izomerizacija" title="スロベニア語: Izomerizacija" lang="sl" hreflang="sl" data-title="Izomerizacija" data-language-autonym="Slovenščina" data-language-local-name="スロベニア語" class="interlanguage-link-target"><span>Slovenščina</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%BC%D0%B5%D1%80%D0%B8%D0%B7%D0%B0%D1%82%D1%81%D0%B8%D1%8F" title="タジク語: Изомеризатсия" lang="tg" hreflang="tg" data-title="Изомеризатсия" data-language-autonym="Тоҷикӣ" data-language-local-name="タジク語" class="interlanguage-link-target"><span>Тоҷикӣ</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%BC%D0%B5%D1%80%D0%B8%D0%B7%D0%B0%D1%86%D1%96%D1%8F" title="ウクライナ語: Ізомеризація" lang="uk" hreflang="uk" data-title="Ізомеризація" data-language-autonym="Українська" data-language-local-name="ウクライナ語" 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/Izomerlanish" title="ウズベク語: Izomerlanish" lang="uz" hreflang="uz" data-title="Izomerlanish" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="ウズベク語" 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%E6%9E%84%E5%8C%96%E5%8F%8D%E5%BA%94" title="中国語: 异构化反应" lang="zh" hreflang="zh" data-title="异构化反应" data-language-autonym="中文" data-language-local-name="中国語" 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/Q903420#sitelinks-wikipedia" title="言語間リンクを編集" class="wbc-editpage">リンクを編集</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="名前空間"> <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/%E7%95%B0%E6%80%A7%E5%8C%96" title="本文を閲覧 [c]" accesskey="c"><span>ページ</span></a></li><li id="ca-talk" class="new vector-tab-noicon mw-list-item"><a href="/w/index.php?title=%E3%83%8E%E3%83%BC%E3%83%88:%E7%95%B0%E6%80%A7%E5%8C%96&action=edit&redlink=1" rel="discussion" class="new" title="「本文ページについての議論」 (存在しないページ) [t]" accesskey="t"><span>ノート</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" class="vector-dropdown-checkbox " aria-label="別の言語に切り替える" > <label id="vector-variants-dropdown-label" for="vector-variants-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" 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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">表示</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">サイドバーに移動</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">非表示</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">出典: フリー百科事典『ウィキペディア(Wikipedia)』</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="ja" dir="ltr"><p><b>異性化</b>(いせいか、Isomerization)は、ある<a href="/wiki/%E5%88%86%E5%AD%90" title="分子">分子</a>が<a href="/wiki/%E5%8E%9F%E5%AD%90" title="原子">原子</a>の組成は全くそのままに、原子の配列が変化して別の分子に変換することである。これらの関連する分子のことは<a href="/wiki/%E7%95%B0%E6%80%A7%E4%BD%93" title="異性体">異性体</a>と呼ぶ<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>。ある条件下で自発的に異性化する分子もある。多くの異性体は、等しいかほぼ等しい<a href="/wiki/%E7%B5%90%E5%90%88%E3%82%A8%E3%83%8D%E3%83%AB%E3%82%AE%E3%83%BC" title="結合エネルギー">結合エネルギー</a>を持ち、そのためほぼ等量が存在する。これらは比較的自由に相互変換でき、即ち2つの異性体間のエネルギー障壁は高くはない。分子間で異性化が起きると、<a href="/wiki/%E8%BB%A2%E4%BD%8D%E5%8F%8D%E5%BF%9C" title="転位反応">転位反応</a>とみなせる。 </p><p><a href="/wiki/%E6%9C%89%E6%A9%9F%E9%87%91%E5%B1%9E%E5%8C%96%E5%90%88%E7%89%A9" class="mw-redirect" title="有機金属化合物">有機金属化合物</a>の異性化の例には、<a href="/wiki/%E7%B5%90%E5%90%88%E7%95%B0%E6%80%A7" class="mw-redirect" title="結合異性">結合異性</a>からの<a href="/w/index.php?title=%E3%83%87%E3%82%AB%E3%83%95%E3%82%A7%E3%83%8B%E3%83%AB%E3%83%95%E3%82%A7%E3%83%AD%E3%82%BB%E3%83%B3&action=edit&redlink=1" class="new" title="「デカフェニルフェロセン」 (存在しないページ)">デカフェニルフェロセン</a>[(η<sup>5</sup>-C<sub>5</sub>Ph<sub>5</sub>)<sub>2</sub>Fe]の生成がある<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><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>。 <span typeof="mw:File"><a href="/wiki/%E3%83%95%E3%82%A1%E3%82%A4%E3%83%AB:Formation_of_decaphenylferrocene_from_its_linkage_isomer.PNG" class="mw-file-description" title="Formation of decaphenylferrocene from its linkage isomer"><img alt="Formation of decaphenylferrocene from its linkage isomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Formation_of_decaphenylferrocene_from_its_linkage_isomer.PNG/500px-Formation_of_decaphenylferrocene_from_its_linkage_isomer.PNG" decoding="async" width="500" height="209" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/2/28/Formation_of_decaphenylferrocene_from_its_linkage_isomer.PNG 1.5x" data-file-width="561" data-file-height="234" /></a></span> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="異性化の事例"><span id=".E7.95.B0.E6.80.A7.E5.8C.96.E3.81.AE.E4.BA.8B.E4.BE.8B"></span>異性化の事例</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E7%95%B0%E6%80%A7%E5%8C%96&action=edit&section=1" title="節を編集: 異性化の事例"><span>編集</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/%E7%82%AD%E5%8C%96%E6%B0%B4%E7%B4%A0" title="炭化水素">炭化水素</a>の<a href="/wiki/%E6%8E%A5%E8%A7%A6%E5%88%86%E8%A7%A3" class="mw-redirect" title="接触分解">接触分解</a>中の異性化は、<a href="/wiki/%E6%9C%89%E6%A9%9F%E5%8C%96%E5%AD%A6" title="有機化学">有機化学</a>においてよく用いられる。燃料中では、<a href="/wiki/%E3%83%9A%E3%83%B3%E3%82%BF%E3%83%B3" title="ペンタン">ペンタン</a>のような直鎖状の異性体は<a href="/wiki/%E7%99%BD%E9%87%91" title="白金">白金</a>触媒の存在下で加熱される。得られた直鎖と分岐の異性体の混合物は、その後に分離される。工業プロセスでは、<a href="/w/index.php?title=N-%E3%83%96%E3%82%BF%E3%83%B3&action=edit&redlink=1" class="new" title="「N-ブタン」 (存在しないページ)">n-ブタン</a>から<a href="/wiki/%E3%82%A4%E3%82%BD%E3%83%96%E3%82%BF%E3%83%B3" title="イソブタン">イソブタン</a>への異性化も行われる。 </p> <dl><dd><span typeof="mw:File"><a href="/wiki/%E3%83%95%E3%82%A1%E3%82%A4%E3%83%AB:N-pentane_isomerization.svg" class="mw-file-description" title="Isomerization of pentane"><img alt="Isomerization of pentane" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/N-pentane_isomerization.svg/500px-N-pentane_isomerization.svg.png" decoding="async" width="500" height="127" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/N-pentane_isomerization.svg/750px-N-pentane_isomerization.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/15/N-pentane_isomerization.svg/1000px-N-pentane_isomerization.svg.png 2x" data-file-width="425" data-file-height="108" /></a></span></dd></dl> <p>“Trans-cis異性化”では、特定の化合物が<a href="/wiki/%E5%B9%BE%E4%BD%95%E7%95%B0%E6%80%A7%E4%BD%93" class="mw-redirect" title="幾何異性体">幾何異性体</a>同士で相互に変換する。例えば、<a href="/wiki/%E3%83%9E%E3%83%AC%E3%82%A4%E3%83%B3%E9%85%B8" title="マレイン酸">マレイン酸</a>や<a href="/wiki/%E3%82%A2%E3%82%BE%E3%83%99%E3%83%B3%E3%82%BC%E3%83%B3" title="アゾベンゼン">アゾベンゼン</a>は、しばしば<a href="/w/index.php?title=%E5%85%89%E7%95%B0%E6%80%A7%E5%8C%96&action=edit&redlink=1" class="new" title="「光異性化」 (存在しないページ)">光異性化</a>する。他の例には、<a href="/wiki/%E3%83%AC%E3%82%B9%E3%83%99%E3%83%A9%E3%83%88%E3%83%AD%E3%83%BC%E3%83%AB" title="レスベラトロール">レスベラトロール</a>のトランス体からシス体への光化学変換がある<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> <dl><dd><span typeof="mw:File"><a href="/wiki/%E3%83%95%E3%82%A1%E3%82%A4%E3%83%AB:Rasveratrol_isomerization-en.svg" class="mw-file-description" title="Resveratrol photoisomerization"><img alt="Resveratrol photoisomerization" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Rasveratrol_isomerization-en.svg/400px-Rasveratrol_isomerization-en.svg.png" decoding="async" width="400" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Rasveratrol_isomerization-en.svg/600px-Rasveratrol_isomerization-en.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/Rasveratrol_isomerization-en.svg/800px-Rasveratrol_isomerization-en.svg.png 2x" data-file-width="1463" data-file-height="567" /></a></span></dd></dl> <p>その他の事例には、<a href="/wiki/%E3%82%B7%E3%82%AF%E3%83%AD%E3%83%98%E3%82%AD%E3%82%B5%E3%83%B3" title="シクロヘキサン">シクロヘキサン</a>の2つの立体配座のように実際の転位が起こらない<a href="/wiki/%E9%85%8D%E5%BA%A7%E7%95%B0%E6%80%A7%E4%BD%93" class="mw-redirect" title="配座異性体">配座異性体</a>間の異性化、生化学における<a href="/wiki/%E3%82%A2%E3%83%AB%E3%83%89%E3%83%BC%E3%82%B9" title="アルドース">アルドース</a>-<a href="/wiki/%E3%82%B1%E3%83%88%E3%83%BC%E3%82%B9" title="ケトース">ケトース</a>異性化、<a href="/wiki/%E3%83%96%E3%83%AB%E3%83%90%E3%83%AC%E3%83%B3" title="ブルバレン">ブルバレン</a>のように異性体間の急速な相互変換が起こる<a href="/w/index.php?title=%E6%B5%81%E5%A4%89%E5%88%86%E5%AD%90&action=edit&redlink=1" class="new" title="「流変分子」 (存在しないページ)">流変分子</a>、<a href="/wiki/%E5%8D%98%E7%B5%90%E5%90%88" class="mw-redirect" title="単結合">単結合</a>と<a href="/wiki/%E4%BA%8C%E9%87%8D%E7%B5%90%E5%90%88" title="二重結合">二重結合</a>の位置が変わるだけの異性化等がある。2つの異性体間のダイナミックな平衡が確立された状態を<a href="/wiki/%E4%BA%92%E5%A4%89%E7%95%B0%E6%80%A7" title="互変異性">互変異性</a>と呼ぶ<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>。 </p><p><a href="/w/index.php?title=%E7%92%B0%E5%8C%96%E7%95%B0%E6%80%A7%E5%8C%96&action=edit&redlink=1" class="new" title="「環化異性化」 (存在しないページ)">環化異性化</a>では、<a href="/wiki/%E7%92%B0%E5%BC%8F%E5%8C%96%E5%90%88%E7%89%A9" title="環式化合物">環式化合物</a>が形成される。 </p><p>2つの異性体間のエネルギーの差は、異性化エネルギーと呼ばれる。実験的にも計算的にも低いエネルギー差の異性化には、<a href="/w/index.php?title=2-%E3%83%96%E3%82%BF%E3%83%B3&action=edit&redlink=1" class="new" title="「2-ブタン」 (存在しないページ)">2-ブタン</a>の吸熱的トランス-シス異性化 (2.6 (1.2) kcal/mol)、<a href="/wiki/%E3%82%A4%E3%82%BD%E3%83%9A%E3%83%B3%E3%82%BF%E3%83%B3" title="イソペンタン">イソペンタン</a>から<a href="/wiki/N-%E3%83%9A%E3%83%B3%E3%82%BF%E3%83%B3" class="mw-redirect" title="N-ペンタン"><i>n</i>-ペンタン</a>への接触分解 (3.6 (4.0) kcal/mol)、<i>trans</i>-<a href="/wiki/2-%E3%83%96%E3%83%86%E3%83%B3" title="2-ブテン">2-ブテン</a>から<a href="/wiki/1-%E3%83%96%E3%83%86%E3%83%B3" title="1-ブテン">1-ブテン</a>への変換 (2.6 (2.4) kcal/mol) 等がある<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>。 </p> <div class="mw-heading mw-heading2"><h2 id="脚注"><span id=".E8.84.9A.E6.B3.A8"></span>脚注</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E7%95%B0%E6%80%A7%E5%8C%96&action=edit&section=2" title="節を編集: 脚注"><span>編集</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="noprint" style="float:right; font-size:90%;">[<a href="/wiki/Help:%E8%84%9A%E6%B3%A8/%E8%AA%AD%E8%80%85%E5%90%91%E3%81%91" title="Help:脚注/読者向け"><span title="この欄の操作法">脚注の使い方</span></a>]</div> <div class="mw-heading mw-heading3"><h3 id="注釈・出典"><span id=".E6.B3.A8.E9.87.88.E3.83.BB.E5.87.BA.E5.85.B8"></span>注釈・出典</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E7%95%B0%E6%80%A7%E5%8C%96&action=edit&section=3" title="節を編集: 注釈・出典"><span>編集</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="reflist" style="list-style-type: decimal;"> <ol class="references"> <li id="cite_note-1"><b><a href="#cite_ref-1">^</a></b> <span class="reference-text"><a href="/wiki/%E5%9B%BD%E9%9A%9B%E7%B4%94%E6%AD%A3%E3%83%BB%E5%BF%9C%E7%94%A8%E5%8C%96%E5%AD%A6%E9%80%A3%E5%90%88" title="国際純正・応用化学連合">IUPAC</a>, <i>Compendium of Chemical Terminology</i>, 2nd ed. (the "Gold Book") (1997). オンライン版:  (2006-) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/I03295.html">isomerization</a>".</span> </li> <li id="cite_note-2"><b><a href="#cite_ref-2">^</a></b> <span class="reference-text"><cite style="font-style:normal" class="citation journal">Brown, K. N.; Field, L. D.; Lay, P. A.; Lindall, C. M.; Masters, A. F. (1990). “(η<sup>5</sup>-Pentaphenylcyclopentadienyl){1-(η<sup>6</sup>-phenyl)-2,3,4,5-tetraphenylcyclopentadienyl}iron(II), [Fe(η<sup>5</sup>-C<sub>5</sub>Ph<sub>5</sub>){(η<sup>6</sup>-C<sub>6</sub>H<sub>5</sub>)C<sub>5</sub>Ph<sub>4</sub>}], a linkage isomer of decaphenylferrocene”. <i>J. Chem. Soc., Chem. Commun.</i> (5): 408–410. <a href="/wiki/Doi_(%E8%AD%98%E5%88%A5%E5%AD%90)" class="mw-redirect" title="Doi (識別子)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC39900000408">10.1039/C39900000408</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=%28%CE%B7%3Csup%3E5%3C%2Fsup%3E-Pentaphenylcyclopentadienyl%29%7B1-%28%CE%B7%3Csup%3E6%3C%2Fsup%3E-phenyl%29-2%2C3%2C4%2C5-tetraphenylcyclopentadienyl%7Diron%28II%29%2C+%5BFe%28%CE%B7%3Csup%3E5%3C%2Fsup%3E-C%3Csub%3E5%3C%2Fsub%3EPh%3Csub%3E5%3C%2Fsub%3E%29%7B%28%CE%B7%3Csup%3E6%3C%2Fsup%3E-C%3Csub%3E6%3C%2Fsub%3EH%3Csub%3E5%3C%2Fsub%3E%29C%3Csub%3E5%3C%2Fsub%3EPh%3Csub%3E4%3C%2Fsub%3E%7D%5D%2C+a+linkage+isomer+of+decaphenylferrocene&rft.jtitle=J.+Chem.+Soc.%2C+Chem.+Commun.&rft.aulast=Brown&rft.aufirst=K.+N.&rft.au=Brown%2C%26%2332%3BK.+N.&rft.au=Field%2C%26%2332%3BL.+D.&rft.au=Lay%2C%26%2332%3BP.+A.&rft.au=Lindall%2C%26%2332%3BC.+M.&rft.au=Masters%2C%26%2332%3BA.+F.&rft.date=1990&rft.issue=5&rft.pages=408%E2%80%93410&rft_id=info:doi/10.1039%2FC39900000408&rfr_id=info:sid/ja.wikipedia.org:%E7%95%B0%E6%80%A7%E5%8C%96"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-3"><b><a href="#cite_ref-3">^</a></b> <span class="reference-text"><cite style="font-style:normal" class="citation journal">Field, L. D.; Hambley, T. W.; Humphrey, P. A.; Lindall, C. M.; Gainsford, G. J.; Masters, A. F.; Stpierre, T. G.; Webb, J. (1995). “Decaphenylferrocene”. <i>Aust. J. Chem.</i> <b>48</b> (4): 851–860. <a href="/wiki/Doi_(%E8%AD%98%E5%88%A5%E5%AD%90)" class="mw-redirect" title="Doi (識別子)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1071%2FCH9950851">10.1071/CH9950851</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Decaphenylferrocene&rft.jtitle=Aust.+J.+Chem.&rft.aulast=Field&rft.aufirst=L.+D.&rft.au=Field%2C%26%2332%3BL.+D.&rft.au=Hambley%2C%26%2332%3BT.+W.&rft.au=Humphrey%2C%26%2332%3BP.+A.&rft.au=Lindall%2C%26%2332%3BC.+M.&rft.au=Gainsford%2C%26%2332%3BG.+J.&rft.au=Masters%2C%26%2332%3BA.+F.&rft.au=Stpierre%2C%26%2332%3BT.+G.&rft.au=Webb%2C%26%2332%3BJ.&rft.date=1995&rft.volume=48&rft.issue=4&rft.pages=851%E2%80%93860&rft_id=info:doi/10.1071%2FCH9950851&rfr_id=info:sid/ja.wikipedia.org:%E7%95%B0%E6%80%A7%E5%8C%96"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-4"><b><a href="#cite_ref-4">^</a></b> <span class="reference-text"><i>Resveratrol Photoisomerization: An Integrative Guided-Inquiry Experiment</i> Elyse Bernard, Philip Britz-McKibbin, Nicholas Gernigon Vol. 84 No. 7 July <b>2007</b> Journal of Chemical Education 1159.</span> </li> <li id="cite_note-5"><b><a href="#cite_ref-5">^</a></b> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.cartage.org.lb/en/themes/Sciences/Chemistry/Organicchemistry/Common/Common.htm">Common Definitions and Terms in Organic Chemistry</a> (from the website of Cartage.org.lb)</span> </li> <li id="cite_note-6"><b><a href="#cite_ref-6">^</a></b> <span class="reference-text"><cite style="font-style:normal" class="citation journal"><a href="/wiki/%E3%82%B7%E3%83%A5%E3%83%86%E3%83%95%E3%82%A1%E3%83%B3%E3%83%BB%E3%82%B0%E3%83%AA%E3%83%A1" title="シュテファン・グリメ">Stefan Grimme</a>, Marc Steinmetz, and Martin Korth (2007). “How to Compute Isomerization Energies of Organic Molecules with Quantum Chemical Methods”. <i><a href="/wiki/J._Org._Chem." class="mw-redirect" title="J. Org. Chem.">J. Org. Chem.</a></i> <b>72</b> (6): 2118–2126. <a href="/wiki/Doi_(%E8%AD%98%E5%88%A5%E5%AD%90)" class="mw-redirect" title="Doi (識別子)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo062446p">10.1021/jo062446p</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=How+to+Compute+Isomerization+Energies+of+Organic+Molecules+with+Quantum+Chemical+Methods&rft.jtitle=%5B%5BJ.+Org.+Chem.%5D%5D&rft.aulast=%5B%5B%E3%82%B7%E3%83%A5%E3%83%86%E3%83%95%E3%82%A1%E3%83%B3%E3%83%BB%E3%82%B0%E3%83%AA%E3%83%A1%7CStefan+Grimme%5D%5D%2C+Marc+Steinmetz%2C+and+Martin+Korth&rft.au=%5B%5B%E3%82%B7%E3%83%A5%E3%83%86%E3%83%95%E3%82%A1%E3%83%B3%E3%83%BB%E3%82%B0%E3%83%AA%E3%83%A1%7CStefan+Grimme%5D%5D%2C+Marc+Steinmetz%2C+and+Martin+Korth&rft.date=2007&rft.volume=72&rft.issue=6&rft.pages=2118%E2%80%932126&rft_id=info:doi/10.1021%2Fjo062446p&rfr_id=info:sid/ja.wikipedia.org:%E7%95%B0%E6%80%A7%E5%8C%96"><span style="display: none;"> </span></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="関連項目"><span id=".E9.96.A2.E9.80.A3.E9.A0.85.E7.9B.AE"></span>関連項目</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E7%95%B0%E6%80%A7%E5%8C%96&action=edit&section=4" title="節を編集: 関連項目"><span>編集</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/%E3%83%A9%E3%82%BB%E3%83%9F%E5%8C%96" title="ラセミ化">ラセミ化</a></li> <li><a href="/wiki/%E3%82%A8%E3%83%94%E3%83%9E%E3%83%BC" title="エピマー">エピマー</a></li> <li><a href="/wiki/%E7%95%B0%E6%80%A7%E5%8C%96%E7%B3%96" title="異性化糖">異性化糖</a></li></ul> <!-- NewPP limit report Parsed by mw‐web.codfw.main‐f69cdc8f6‐ffqzr Cached time: 20241123215909 Cache expiry: 2592000 Reduced expiry: false Complications: [show‐toc] CPU time usage: 0.094 seconds Real time usage: 0.206 seconds Preprocessor visited node count: 2747/1000000 Post‐expand include size: 24784/2097152 bytes Template argument size: 5569/2097152 bytes Highest expansion depth: 26/100 Expensive parser function count: 0/500 Unstrip recursion depth: 0/20 Unstrip post‐expand size: 6843/5000000 bytes Lua time usage: 0.004/10.000 seconds Lua memory usage: 913981/52428800 bytes Number of Wikibase entities loaded: 0/400 --> <!-- Transclusion expansion time report (%,ms,calls,template) 100.00% 69.263 1 -total 97.31% 67.399 1 Template:Reflist 83.13% 57.575 3 Template:Cite_journal 75.08% 52.003 3 Template:Citation/core 26.16% 18.116 3 Template:ISO639言語名 9.15% 6.339 3 Template:Citation/identifier 5.45% 3.776 3 Template:Doi 4.44% 3.077 1 Template:GoldBookRef 4.35% 3.014 3 Template:Link 2.55% 1.764 1 Template:脚注ヘルプ --> <!-- Saved in parser cache with key jawiki:pcache:idhash:132244-0!canonical and timestamp 20241123215909 and revision id 98604417. 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