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Available in 25 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-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 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D8%B5%D8%A7%D9%88%D8%BA%D8%A9" title="مصاوغة – Arabic" lang="ar" hreflang="ar" data-title="مصاوغة" data-language-autonym="العربية" data-language-local-name="Arabic" 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="সমাণুকরণ – Bangla" lang="bn" hreflang="bn" data-title="সমাণুকরণ" data-language-autonym="বাংলা" data-language-local-name="Bangla" 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="Izomerizacija – Bosnian" lang="bs" hreflang="bs" data-title="Izomerizacija" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Isomeritzaci%C3%B3" title="Isomerització – Catalan" lang="ca" hreflang="ca" data-title="Isomerització" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Izomerizace" title="Izomerizace – Czech" lang="cs" hreflang="cs" data-title="Izomerizace" data-language-autonym="Čeština" data-language-local-name="Czech" 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="Isomerisierung – German" lang="de" hreflang="de" data-title="Isomerisierung" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Isomerisatsioon" title="Isomerisatsioon – Estonian" lang="et" hreflang="et" data-title="Isomerisatsioon" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Isomerizaci%C3%B3n" title="Isomerización – Spanish" lang="es" hreflang="es" data-title="Isomerización" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</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="همپاری – Persian" lang="fa" hreflang="fa" data-title="همپاری" data-language-autonym="فارسی" data-language-local-name="Persian" 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="Isomerización – Galician" lang="gl" hreflang="gl" data-title="Isomerización" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</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="이성질체화 반응 – Korean" lang="ko" hreflang="ko" data-title="이성질체화 반응" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</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="Իզոմերացում – Armenian" lang="hy" hreflang="hy" data-title="Իզոմերացում" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Pengisomeran" title="Pengisomeran – Malay" lang="ms" hreflang="ms" data-title="Pengisomeran" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" 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="Isomerisatie – Dutch" lang="nl" hreflang="nl" data-title="Isomerisatie" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E7%95%B0%E6%80%A7%E5%8C%96" title="異性化 – Japanese" lang="ja" hreflang="ja" data-title="異性化" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Izomerlanish" title="Izomerlanish – Uzbek" lang="uz" hreflang="uz" data-title="Izomerlanish" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Izomeryzacja" title="Izomeryzacja – Polish" lang="pl" hreflang="pl" data-title="Izomeryzacja" data-language-autonym="Polski" data-language-local-name="Polish" 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="Izomerizare – Romanian" lang="ro" hreflang="ro" data-title="Izomerizare" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%98%D0%B7%D0%BE%D0%BC%D0%B5%D1%80%D0%B8%D0%B7%D0%B0%D1%86%D0%B8%D1%8F" title="Изомеризация – Russian" lang="ru" hreflang="ru" data-title="Изомеризация" data-language-autonym="Русский" data-language-local-name="Russian" 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="Isomerization – Simple English" lang="en-simple" hreflang="en-simple" data-title="Isomerization" data-language-autonym="Simple English" data-language-local-name="Simple English" 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="Izomerizácia – Slovak" lang="sk" hreflang="sk" data-title="Izomerizácia" data-language-autonym="Slovenčina" data-language-local-name="Slovak" 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="Izomerizacija – Slovenian" lang="sl" hreflang="sl" data-title="Izomerizacija" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" 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="Изомеризатсия – Tajik" lang="tg" hreflang="tg" data-title="Изомеризатсия" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" 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="Ізомеризація – Ukrainian" lang="uk" hreflang="uk" data-title="Ізомеризація" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a 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</div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Transformation of the chemical structure of a molecule or ion</div> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, <b>isomerization</b> or <b>isomerisation</b> is the process in which a <a href="/wiki/Molecule" title="Molecule">molecule</a>, <a href="/wiki/Polyatomic_ion" title="Polyatomic ion">polyatomic ion</a> or molecular fragment is transformed into an <a href="/wiki/Isomer" title="Isomer">isomer</a> with a different <a href="/wiki/Chemical_structure" title="Chemical structure">chemical structure</a>.<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> <a href="/wiki/Enolization" class="mw-redirect" title="Enolization">Enolization</a> is an example of isomerization, as is <a href="/wiki/Tautomer" title="Tautomer">tautomerization</a>.<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> When the isomerization occurs <a href="/wiki/Intramolecular_reaction" title="Intramolecular reaction">intramolecularly</a> it may be called a <a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">rearrangement reaction</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2021)">citation needed</span></a></i>]</sup> </p><p>When the <a href="/wiki/Activation_energy" title="Activation energy">activation energy</a> for the isomerization reaction is sufficiently small, both isomers will exist in a temperature-dependent <a href="/wiki/Chemical_equilibrium" title="Chemical equilibrium">equilibrium</a> with each other. Many values of the standard <a href="/wiki/Thermodynamic_free_energy" title="Thermodynamic free energy">free energy</a> difference, <span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle \Delta G^{\circ }}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi mathvariant="normal">Δ</mi> <msup> <mi>G</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>∘</mo> </mrow> </msup> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \Delta G^{\circ }}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/340aca3436e1f5d1e57a730f5131bf497801a762" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.338ex; width:4.817ex; height:2.343ex;" alt="{\displaystyle \Delta G^{\circ }}"></span>, have been calculated, with good agreement between observed and calculated data.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Examples_and_applications">Examples and applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerization&action=edit&section=1" title="Edit section: Examples and applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Alkanes">Alkanes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerization&action=edit&section=2" title="Edit section: Alkanes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Skeletal isomerization occurs in the <a href="/wiki/Cracking_(chemistry)" title="Cracking (chemistry)">cracking</a> process, used in the <a href="/wiki/Petrochemical" title="Petrochemical">petrochemical</a> industry to convert straight chain alkanes to <a href="/wiki/Isoparaffin" class="mw-redirect" title="Isoparaffin">isoparaffins</a> as exemplified in the conversion of <a href="/wiki/Octane" title="Octane">normal octane</a> to <a href="/wiki/2,5-Dimethylhexane" title="2,5-Dimethylhexane">2,5-dimethylhexane</a> (an "isoparaffin"):<sup id="cite_ref-Ullmann_4-0" class="reference"><a href="#cite_note-Ullmann-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:Paraffintoisoparaffin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Paraffintoisoparaffin.svg/512px-Paraffintoisoparaffin.svg.png" decoding="async" width="512" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Paraffintoisoparaffin.svg/768px-Paraffintoisoparaffin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Paraffintoisoparaffin.svg/1024px-Paraffintoisoparaffin.svg.png 2x" data-file-width="512" data-file-height="89" /></a><figcaption></figcaption></figure></dd></dl> <p>Fuels containing branched <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a> are favored for internal combustion engines for their higher <a href="/wiki/Octane_rating" title="Octane rating">octane rating</a>.<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> <div class="mw-heading mw-heading3"><h3 id="Alkenes">Alkenes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerization&action=edit&section=3" title="Edit section: Alkenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Trans-alkenes are about 1 kcal/mol more stable than cis-alkenes. An example of this effect is cis- vs trans-2-butene. The difference is attributed to unfavorable non-bonded interactions in the cis isomer. </p><p>Terminal alkenes isomerize to internal alkenes in the presence of metal catalysts. This process is employed in the <a href="/wiki/Shell_higher_olefin_process" title="Shell higher olefin process">Shell higher olefin process</a> to convert alpha-olefins to internal olefins, which are subjected to <a href="/wiki/Olefin_metathesis" title="Olefin metathesis">olefin metathesis</a>. In certain kinds of alkene polymerization reactions, <a href="/wiki/Chain_walking" title="Chain walking">chain walking</a> is an isomerization process that introduces branches into growing polymers.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2021)">citation needed</span></a></i>]</sup> </p><p>The <i>trans</i> isomer of <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a> can be converted to the <i>cis</i> isomer in a <a href="/wiki/Photochemical_reaction" class="mw-redirect" title="Photochemical reaction">photochemical reaction</a>.<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> <dl><dd><span typeof="mw:File"><a href="/wiki/File: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><a href="/wiki/Thermal_rearrangement_of_aromatic_hydrocarbons" title="Thermal rearrangement of aromatic hydrocarbons">Thermal rearrangement</a> of <a href="/wiki/Azulene" title="Azulene">azulene</a> to <a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a> has been observed.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_examples">Other examples</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerization&action=edit&section=4" title="Edit section: Other examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Aldose-ketose_isomerization" class="mw-redirect" title="Aldose-ketose isomerization">Aldose-ketose isomerism</a>, also known as Lobry de Bruyn–van Ekenstein transformation, provides an example in <a href="/wiki/Saccharide_chemistry" class="mw-redirect" title="Saccharide chemistry">saccharide chemistry</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (September 2021)">citation needed</span></a></i>]</sup> </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Lobry-de-Bruyn-Alberda-van-Ekenstein-Umlagerung.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Lobry-de-Bruyn-Alberda-van-Ekenstein-Umlagerung.svg/500px-Lobry-de-Bruyn-Alberda-van-Ekenstein-Umlagerung.svg.png" decoding="async" width="500" height="79" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Lobry-de-Bruyn-Alberda-van-Ekenstein-Umlagerung.svg/750px-Lobry-de-Bruyn-Alberda-van-Ekenstein-Umlagerung.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Lobry-de-Bruyn-Alberda-van-Ekenstein-Umlagerung.svg/1000px-Lobry-de-Bruyn-Alberda-van-Ekenstein-Umlagerung.svg.png 2x" data-file-width="1165" data-file-height="183" /></a><figcaption></figcaption></figure></dd></dl> <p>An example of an <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic</a> isomerization is the production of decaphenylferrocene, <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">[(η<sup>5</sup>-C<sub class="template-chem2-sub">5</sub><a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">Ph</a><sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>Fe]</span> from its <a href="/wiki/Linkage_isomer" class="mw-redirect" title="Linkage isomer">linkage isomer</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Formation_of_decaphenylferrocene_from_its_linkage_isomer.svg" 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/8/88/Formation_of_decaphenylferrocene_from_its_linkage_isomer.svg/380px-Formation_of_decaphenylferrocene_from_its_linkage_isomer.svg.png" decoding="async" width="380" height="156" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Formation_of_decaphenylferrocene_from_its_linkage_isomer.svg/570px-Formation_of_decaphenylferrocene_from_its_linkage_isomer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/88/Formation_of_decaphenylferrocene_from_its_linkage_isomer.svg/760px-Formation_of_decaphenylferrocene_from_its_linkage_isomer.svg.png 2x" data-file-width="363" data-file-height="149" /></a><figcaption>Formation of decaphenylferrocene from its linkage isomer</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerization&action=edit&section=5" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Base-promoted_epoxide_isomerization" title="Base-promoted epoxide isomerization">Base-promoted epoxide isomerization</a></li> <li><a href="/wiki/Epimerization" class="mw-redirect" title="Epimerization">Epimerization</a></li> <li><a href="/wiki/Racemization" title="Racemization">Racemization</a></li> <li><a href="/wiki/Tautomerization" class="mw-redirect" title="Tautomerization">Tautomerization</a></li> <li><a href="/wiki/Linkage_isomerism" title="Linkage isomerism">Linkage isomerism</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerization&action=edit&section=6" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/I03295.html">isomerization</a>". <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.I03295">10.1351/goldbook.I03295</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAntonov_L2016" class="citation book cs1">Antonov L (2016). <i>Tautomerism: Concepts and Applications in Science and Technology</i> (1st ed.). Weinheim, Germany: Wiley-VCH. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-33995-2" title="Special:BookSources/978-3-527-33995-2"><bdi>978-3-527-33995-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Tautomerism%3A+Concepts+and+Applications+in+Science+and+Technology&rft.place=Weinheim%2C+Germany&rft.edition=1st&rft.pub=Wiley-VCH&rft.date=2016&rft.isbn=978-3-527-33995-2&rft.au=Antonov+L&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerization" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><i>How to Compute Isomerization Energies of Organic Molecules with Quantum Chemical Methods</i> <a href="/wiki/Stefan_Grimme" title="Stefan Grimme">Stefan Grimme</a>, Marc Steinmetz, and Martin Korth <a href="/wiki/J._Org._Chem." class="mw-redirect" title="J. Org. Chem.">J. Org. Chem.</a>; <b>2007</b>; 72(6) pp 2118 - 2126; (Article) <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo062446p">10.1021/jo062446p</a></span> </li> <li id="cite_note-Ullmann-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ullmann_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIrionNeuwirth2000" class="citation book cs1">Irion, Walther W.; Neuwirth, Otto S. (2000). "Oil Refining". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a18_051">10.1002/14356007.a18_051</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3-527-30673-0" title="Special:BookSources/3-527-30673-0"><bdi>3-527-30673-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Oil+Refining&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F14356007.a18_051&rft.isbn=3-527-30673-0&rft.aulast=Irion&rft.aufirst=Walther+W.&rft.au=Neuwirth%2C+Otto+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerization" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKarl_GriesbaumArno_BehrDieter_BiedenkappHeinz-Werner_Voges2002" class="citation encyclopaedia cs1">Karl Griesbaum; Arno Behr; Dieter Biedenkapp; Heinz-Werner Voges; Dorothea Garbe; Christian Paetz; Gerd Collin; Dieter Mayer; Hartmut Höke (2002). "Hydrocarbons". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a13_227">10.1002/14356007.a13_227</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3-527-30673-0" title="Special:BookSources/3-527-30673-0"><bdi>3-527-30673-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hydrocarbons&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2002&rft_id=info%3Adoi%2F10.1002%2F14356007.a13_227&rft.isbn=3-527-30673-0&rft.au=Karl+Griesbaum&rft.au=Arno+Behr&rft.au=Dieter+Biedenkapp&rft.au=Heinz-Werner+Voges&rft.au=Dorothea+Garbe&rft.au=Christian+Paetz&rft.au=Gerd+Collin&rft.au=Dieter+Mayer&rft.au=Hartmut+H%C3%B6ke&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerization" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFElyse_Bernard,_Philip_Britz-McKibbin,_Nicholas_Gernigon2007" class="citation journal cs1">Elyse Bernard, Philip Britz-McKibbin, Nicholas Gernigon (2007). "Resveratrol Photoisomerization: An Integrative Guided-Inquiry Experiment'<span class="cs1-kern-right"></span>". <i>Journal of Chemical Education</i>. <b>84</b>: 1159.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chemical+Education&rft.atitle=Resveratrol+Photoisomerization%3A+An+Integrative+Guided-Inquiry+Experiment%27&rft.volume=84&rft.pages=1159&rft.date=2007&rft.au=Elyse+Bernard%2C+Philip+Britz-McKibbin%2C+Nicholas+Gernigon&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerization" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBeckerWentrupZellerKatz1980" class="citation journal cs1">Becker, Juergen; Wentrup, Curt; Zeller, Klaus; Katz, Ellen (July 1, 1980). <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/abs/10.1021/ja00535a056">"Azulene-naphthalene rearrangement. Involvement of 1-phenylbuten-3-ynes and 4-phenyl-1,3-butadienylidene"</a>. <i>J. Am. Chem. Soc</i>. <b>102</b> (15): 5110. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00535a056">10.1021/ja00535a056</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Azulene-naphthalene+rearrangement.+Involvement+of+1-phenylbuten-3-ynes+and+4-phenyl-1%2C3-butadienylidene&rft.volume=102&rft.issue=15&rft.pages=5110&rft.date=1980-07-01&rft_id=info%3Adoi%2F10.1021%2Fja00535a056&rft.aulast=Becker&rft.aufirst=Juergen&rft.au=Wentrup%2C+Curt&rft.au=Zeller%2C+Klaus&rft.au=Katz%2C+Ellen&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2Fabs%2F10.1021%2Fja00535a056&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerization" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBrownFieldLayLindall1990" class="citation journal cs1">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><a href="/wiki/Chemical_Communications" class="mw-redirect" title="Chemical Communications">J. Chem. Soc., Chem. Commun.</a></i> (5): 408–410. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC39900000408">10.1039/C39900000408</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Chem.+Soc.%2C+Chem.+Commun.&rft.atitle=%28%26eta%3B%3Csup%3E5%3C%2Fsup%3E-Pentaphenylcyclopentadienyl%29%7B1-%28%26eta%3B%3Csup%3E6%3C%2Fsup%3E-phenyl%29-2%2C3%2C4%2C5-tetraphenylcyclopentadienyl%7Diron%28II%29%2C+%5BFe%28%26eta%3B%3Csup%3E5%3C%2Fsup%3E-C%3Csub%3E5%3C%2Fsub%3EPh%3Csub%3E5%3C%2Fsub%3E%29%7B%28%26eta%3B%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.issue=5&rft.pages=408-410&rft.date=1990&rft_id=info%3Adoi%2F10.1039%2FC39900000408&rft.aulast=Brown&rft.aufirst=K.+N.&rft.au=Field%2C+L.+D.&rft.au=Lay%2C+P.+A.&rft.au=Lindall%2C+C.+M.&rft.au=Masters%2C+A.+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerization" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFieldHambleyHumphreyLindall1995" class="citation journal cs1">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_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1071%2FCH9950851">10.1071/CH9950851</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Aust.+J.+Chem.&rft.atitle=Decaphenylferrocene&rft.volume=48&rft.issue=4&rft.pages=851-860&rft.date=1995&rft_id=info%3Adoi%2F10.1071%2FCH9950851&rft.aulast=Field&rft.aufirst=L.+D.&rft.au=Hambley%2C+T.+W.&rft.au=Humphrey%2C+P.+A.&rft.au=Lindall%2C+C.+M.&rft.au=Gainsford%2C+G.+J.&rft.au=Masters%2C+A.+F.&rft.au=Stpierre%2C+T.+G.&rft.au=Webb%2C+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerization" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output 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title="SN1 reaction">Unimolecular nucleophilic substitution</a> (S<sub>N</sub>1)</li> <li><a href="/wiki/SN2_reaction" title="SN2 reaction">Bimolecular nucleophilic substitution</a> (S<sub>N</sub>2)</li> <li><a href="/wiki/Nucleophilic_aromatic_substitution" title="Nucleophilic aromatic substitution">Nucleophilic aromatic substitution</a> (S<sub>N</sub>Ar)</li> <li><a href="/wiki/SNi" title="SNi">Nucleophilic internal substitution</a> (S<sub>N</sub>i)</li> <li><a href="/wiki/Nucleophilic_acyl_substitution" class="mw-redirect" title="Nucleophilic acyl substitution">Nucleophilic acyl substitution</a> (S<sub>N</sub>Acyl)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Electrophilic_substitution" title="Electrophilic substitution">Electrophilic substitutions</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">Electrophilic aromatic substitution</a> (S<sub>E</sub>Ar)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination reactions</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/E1_elimination" class="mw-redirect" title="E1 elimination">Unimolecular elimination</a> (E1)</li> <li><a href="/wiki/E1cB-elimination_reaction" title="E1cB-elimination reaction">E1cB-elimination</a></li> <li><a href="/wiki/E2_elimination" class="mw-redirect" title="E2 elimination">Bimolecular elimination</a> (E2)</li> <li><a href="/wiki/Ei_mechanism" title="Ei mechanism">E<sub>i</sub> elimination</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Addition_reaction" title="Addition reaction">Addition reactions</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electrophilic_addition" title="Electrophilic addition">Electrophilic addition</a> (A<sub>E</sub>)</li> <li><a href="/wiki/Nucleophilic_addition" title="Nucleophilic addition">Nucleophilic addition</a> (A<sub>N</sub>)</li> <li><a href="/wiki/Free-radical_addition" title="Free-radical addition">Free-radical addition</a></li> <li><a href="/wiki/Cycloaddition" title="Cycloaddition">Cycloaddition</a></li> <li><a href="/wiki/Oxidative_addition" title="Oxidative addition">Oxidative addition</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Unimolecular reactions</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Intramolecular_reaction" title="Intramolecular reaction">Intramolecular reaction</a></li> <li><a class="mw-selflink selflink">Isomerization</a></li> <li><a href="/wiki/Photodissociation" title="Photodissociation">Photodissociation</a></li> <li><a href="/wiki/Lindemann%E2%80%93Hinshelwood_mechanism" class="mw-redirect" title="Lindemann–Hinshelwood mechanism">Lindemann–Hinshelwood mechanism</a></li> <li><a href="/wiki/RRKM_theory" title="RRKM theory">RRKM theory</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Electron_transfer" title="Electron transfer">Electron/Proton transfer</a> reactions</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Redox" title="Redox">Redox</a></li> <li><a href="/wiki/Harpoon_reaction" title="Harpoon reaction">Harpoon reaction</a></li> <li><a href="/wiki/Grotthuss_mechanism" title="Grotthuss mechanism">Grotthuss mechanism</a></li> <li><a href="/wiki/Marcus_theory" title="Marcus theory">Marcus theory</a></li> <li><a href="/wiki/Inner_sphere_electron_transfer" title="Inner sphere electron transfer">Inner sphere electron transfer</a></li> <li><a href="/wiki/Outer_sphere_electron_transfer" title="Outer sphere electron transfer">Outer sphere electron transfer</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Medium effects</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Solvent_effects" title="Solvent effects">Solvent effects</a></li> <li><a href="/wiki/Cage_effect" title="Cage effect">Cage effect</a></li> <li><a href="/wiki/Matrix_isolation" title="Matrix isolation">Matrix isolation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related topics</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Elementary_reaction" title="Elementary reaction">Elementary reaction</a></li> <li><a href="/wiki/Reaction_dynamics" title="Reaction dynamics">Reaction dynamics</a></li> <li><a href="/wiki/Reactive_intermediate" title="Reactive intermediate">Reactive intermediate</a></li> <li><a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">Radical (chemistry)</a></li> <li><a href="/wiki/Molecularity" title="Molecularity">Molecularity</a></li> <li><a href="/wiki/Stereochemistry" title="Stereochemistry">Stereochemistry</a></li> <li><a href="/wiki/Catalysis" title="Catalysis">Catalysis</a></li> <li><a href="/wiki/Collision_theory" title="Collision theory">Collision theory</a></li> <li><a href="/wiki/Arrow_pushing" title="Arrow pushing">Arrow pushing</a></li> <li><a href="/wiki/Potential_energy_surface" title="Potential energy surface">Potential energy surface</a></li> <li><a href="/wiki/More_O%27Ferrall%E2%80%93Jencks_plot" title="More O'Ferrall–Jencks plot">More O'Ferrall–Jencks plot</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chemical_kinetics" title="Chemical kinetics">Chemical kinetics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Rate_equation" title="Rate equation">Rate equation</a></li> <li><a href="/wiki/Equilibrium_constant" title="Equilibrium constant">Equilibrium constant</a></li> <li><a href="/wiki/Rate-determining_step" title="Rate-determining step">Rate-determining step</a></li> <li><a href="/wiki/Reaction_coordinate" title="Reaction coordinate">Reaction coordinate</a></li> <li><a href="/wiki/Energy_profile_(chemistry)" title="Energy profile (chemistry)">Energy profile (chemistry)</a></li> <li><a href="/wiki/Transition_state_theory" title="Transition state theory">Transition state theory</a></li> <li><a href="/wiki/Activation_energy" title="Activation energy">Activation energy</a></li> <li><a href="/wiki/Activated_complex" title="Activated complex">Activated complex</a></li> <li><a href="/wiki/Arrhenius_equation" title="Arrhenius equation">Arrhenius equation</a></li> <li><a href="/wiki/Eyring_equation" title="Eyring equation">Eyring equation</a></li> <li><a href="/wiki/Michaelis%E2%80%93Menten_kinetics" title="Michaelis–Menten kinetics">Michaelis–Menten kinetics</a></li> <li><a href="/wiki/Diffusion-controlled_reaction" title="Diffusion-controlled reaction">Diffusion-controlled reaction</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" 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