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<title>Isomerization</title>

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<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Isomerization</span></span>

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<p>In <a href="Chemistry" title="Chemistry">chemistry</a>, <b>isomerization</b> or <b>isomerisation</b> is the process in which a <a href="Molecule" title="Molecule">molecule</a>, <a href="Polyatomic_ion" title="Polyatomic ion">polyatomic ion</a> or molecular fragment is transformed into an <a href="Isomer" title="Isomer">isomer</a> with a different <a href="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="Enolization" class="mw-redirect" title="Enolization">Enolization</a> is an example of isomerization, as is <a href="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>

</p><p>When the <a href="Activation_energy" title="Activation energy">activation energy</a> for the isomerization reaction is sufficiently small, both isomers can often be observed and the equilibrium ratio will shift in a temperature-dependent <a href="Chemical_equilibrium" title="Chemical equilibrium">equilibrium</a> with each other. Many values of the standard <a href="Thermodynamic_free_energy" title="Thermodynamic free energy">free energy</a> difference, <span class="mwe-math-element mwe-math-element-inline"><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 }}">

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<annotation encoding="application/x-tex">{\displaystyle \Delta G^{\circ }}</annotation>

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</math></span><img src="./340aca3436e1f5d1e57a730f5131bf497801a762.svg" 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 }}" loading="lazy"></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>

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<div class="mw-heading mw-heading2"><h2 id="Examples_and_applications">Examples and applications</h2></div>

<div class="mw-heading mw-heading3"><h3 id="Alkanes">Alkanes</h3></div>

<p>Skeletal isomerization occurs in the <a href="Cracking_(chemistry)" title="Cracking (chemistry)">cracking</a> process, used in the <a href="Petrochemical" title="Petrochemical">petrochemical</a> industry to convert straight chain alkanes to <a href="Isoparaffin" class="mw-redirect" title="Isoparaffin">isoparaffins</a> as exemplified in the conversion of <a href="Octane" title="Octane">normal octane</a> to <a href="2%2C5-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>

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<p>Fuels containing branched <a href="Hydrocarbon" title="Hydrocarbon">hydrocarbons</a> are favored for internal combustion engines for their higher <a href="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> Diesel engines however operate better with straight-chain hydrocarbons.

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<div class="mw-heading mw-heading3"><h3 id="Alkenes">Alkenes</h3></div>

<div class="mw-heading mw-heading4"><h4 id="Cis_vs_trans">Cis vs trans</h4></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. This effects helps to explain the formation of trans-fats in food processing. In some cases, the isomerization can be reversed using UV-light. The <i>trans</i> isomer of <a href="Resveratrol" title="Resveratrol">resveratrol</a> converts to the <i>cis</i> isomer in a <a href="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>

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<div class="mw-heading mw-heading4"><h4 id="Terminal_vs_internal">Terminal vs internal</h4></div>

<p>Terminal alkenes prefer to isomerize to internal alkenes:

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</style><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>C=CHCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub> → CH<sub class="template-chem2-sub">3</sub>CH=CHCH<sub class="template-chem2-sub">3</sub></span></dd></dl>

<p>The conversion essentially does not occur in the absence of metal catalysts. This process is employed in the <a href="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="Olefin_metathesis" title="Olefin metathesis">olefin metathesis</a>.

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<div class="mw-heading mw-heading3"><h3 id="Other_organic_examples">Other organic examples</h3></div>

<p>Isomerism is a major topic in sugar chemistry. <a href="Glucose" title="Glucose">Glucose</a>, the most common sugar, exists in four forms.

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<th colspan="3">Isomers of <style data-mw-deduplicate="TemplateStyles:r920966791">

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</style><span class="smallcaps">d</span>-glucose

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<td align="center"><span class="skin-invert-image" typeof="mw:File"></span><div class="paragraphbreak" style="margin-top:0.5em"></div>α-<span class="smallcaps">d</span>-glucofuranose

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<td align="center"><span class="skin-invert-image" typeof="mw:File"></span><div class="paragraphbreak" style="margin-top:0.5em"></div>β-<span class="smallcaps">d</span>-glucofuranose

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<td align="center"><span class="skin-invert-image" typeof="mw:File"></span><div class="paragraphbreak" style="margin-top:0.5em"></div>α-<span class="smallcaps">d</span>-glucopyranose

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<td align="center"><span class="skin-invert-image" typeof="mw:File"></span><div class="paragraphbreak" style="margin-top:0.5em"></div>β-<span class="smallcaps">d</span>-glucopyranose

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<p><a href="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="Saccharide_chemistry" class="mw-redirect" title="Saccharide chemistry">saccharide chemistry</a>.<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>

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<div class="mw-heading mw-heading3"><h3 id="Inorganic_and_organometallic_chemistry">Inorganic and organometallic chemistry</h3></div>

<p>The compound with the formula <a href="Cyclopentadienyliron_dicarbonyl_dimer" title="Cyclopentadienyliron dicarbonyl dimer"><span class="chemf nowrap">(C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>Fe<sub class="template-chem2-sub">2</sub>(CO)<sub class="template-chem2-sub">4</sub></span></a> exists as three isomers in solution. In one isomer the CO ligands are terminal. When a pair of CO are <a href="Bridging_ligand" title="Bridging ligand">bridging</a>,

cis and trans isomers are possible depending on the location of the <a href="Cyclopentadienyl_ligand" class="mw-redirect" title="Cyclopentadienyl ligand">C<sub>5</sub>H<sub>5</sub> groups</a>.<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><p>Another example in <a href="Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a> is the <a href="Linkage_isomer" class="mw-redirect" title="Linkage isomer">linkage isomerization</a> of decaphenylferrocene, <span class="chemf nowrap">[(η<sup>5</sup>-C<sub class="template-chem2-sub">5</sub><a href="Phenyl" class="mw-redirect" title="Phenyl">Ph</a><sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>Fe]</span>.<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><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup>

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<div class="mw-heading mw-heading2"><h2 id="Kinetic_classification">Kinetic classification</h2></div>

<p>From the <a href="Chemical_kinetics" title="Chemical kinetics">kinetic viewpoint</a>, isomerizations can be classified into two categories.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Cases in the first category involve transformations between equivalent structures. Most chemical species are in principle susceptible to such processes. Many such cases involve <a href="Fluxional_molecule" title="Fluxional molecule">fluxional molecules</a>, such as the <a href="Cyclohexane_conformation" title="Cyclohexane conformation">cyclohexane ring flip</a> (chair inversion), the <a href="Pyramidal_inversion" title="Pyramidal inversion">pyramidal inversion</a> of ammonia, the <a href="Berry_mechanism" title="Berry mechanism">Berry pseudorotation</a> in pentacoordinate compounds (e.g. PF<sub>5</sub>, Fe(CO)<sub>5</sub>), the <a href="Bullvalene" title="Bullvalene">Cope rearrangements of bullvalene</a> or the <a href="Ray%E2%80%93Dutt_twist" title="Ray–Dutt twist">Ray-Dutt</a>/<a href="Bailar_twist" title="Bailar twist">Bailar twists</a> for the racemization of octahedral complexes with three bidentate chelate rings (<a href="Axial_chirality" title="Axial chirality">helical chirality</a>).

</p><p>In the second broad category of isomerizations, the isomers are nonequivalent. Examples include <a href="Tautomer" title="Tautomer">tautomerizations</a> (<a href="Enol" title="Enol">keto-enol</a>, <a href="Lactam" title="Lactam">lactam-lactim</a>, <a href="Imidic_acid" title="Imidic acid">amide-imidic</a>, <a href="Enamine" title="Enamine">enamine-imine</a>, <a href="Nitroso" title="Nitroso">nitroso-oxime</a>, <a href="Ketene" title="Ketene">ketene-ynol</a>, etc) in which one isomer is more stable than the other.

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<p>This scheme leads to the following system of differential <a href="Rate_equation" title="Rate equation">rate equations</a>:

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<ul><li><a href="Base-promoted_epoxide_isomerization" title="Base-promoted epoxide isomerization">Base-promoted epoxide isomerization</a></li>

<li><a href="Epimerization" class="mw-redirect" title="Epimerization">Epimerization</a></li>

<li><a href="Racemization" title="Racemization">Racemization</a></li>

<li><a href="Tautomerization" class="mw-redirect" title="Tautomerization">Tautomerization</a></li>

<li><a href="Linkage_isomerism" title="Linkage isomerism">Linkage isomerism</a></li></ul>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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<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="International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="IUPAC_books" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 5th ed. (the "Gold Book") (2025). Online 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">

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</style><a href="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"><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="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-3-527-33995-2</bdi>.</cite></span>

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<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="Stefan_Grimme" title="Stefan Grimme">Stefan Grimme</a>, Marc Steinmetz, and Martin Korth <a href="J._Org._Chem." class="mw-redirect" title="J. Org. Chem.">J. Org. Chem.</a>; <b>2007</b>; 72(6) pp 2118 – 2126; (Article) <a href="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>

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<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"><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="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="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>3-527-30673-0</bdi>.</cite></span>

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<li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><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="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="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>3-527-30673-0</bdi>.</cite></span>

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<li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><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'". <i>Journal of Chemical Education</i>. <b>84</b> (7): 1159. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2007JChEd..84.1159B">2007JChEd..84.1159B</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fed084p1159">10.1021/ed084p1159</a>.</cite><span class="cs1-maint citation-comment"><code class="cs1-code">{{cite journal}}</code>: CS1 maint: multiple names: authors list (link)</span></span>

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<li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.oxfordreference.com/display/10.1093/oi/authority.20110803100111253">"Lobry de Bruyn-van Ekenstein transformation"</a>. <i>Oxford Reference</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2025-07-08</span></span>.</cite></span>

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<li id="cite_note-:2-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-:2_8-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFHarrisRosenbergRoberts1974" class="citation journal cs1">Harris, Daniel C.; Rosenberg, Edward; Roberts, John D. (1974). <a rel="nofollow" class="external text" href="https://authors.library.caltech.edu/12272/1/HARjcsdt74.pdf">"Carbon-13 nuclear magnetic resonance spectra and mechanism of bridge–terminal carbonyl exchange in di-<i>µ</i>-carbonyl-bis[carbonyl(<i>η</i>-cyclopentadienyl)iron](Fe–Fe) [{(<i>η</i>-C<sub>5</sub>H<sub>5</sub>)Fe(CO)<sub>2</sub>}<sub>2</sub>]; <i>cd</i>-di-<i>µ</i>-carbonyl-<i>f</i>-carbonyl-<i>ae</i>-di(<i>η</i>-cyclopentadienyl)-<i>b</i>-(triethyl-phosphite)di-iron(Fe–Fe) [(<i>η</i>-C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>Fe<sub>2</sub>(CO)<sub>3</sub>P(OEt)<sub>3</sub>], and some related complexes"</a> <span class="cs1-format">(PDF)</span>. <i>Journal of the Chemical Society: Dalton Transactions</i> (22): <span class="nowrap">2398–</span>2403. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FDT9740002398">10.1039/DT9740002398</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0300-9246">0300-9246</a>.</cite></span>

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<li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><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="Chemical_Communications" class="mw-redirect" title="Chemical Communications">J. Chem. Soc., Chem. Commun.</a></i> (5): <span class="nowrap">408–</span>410. <a href="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>

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<li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><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): <span class="nowrap">851–</span>860. <a href="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>

</li>

<li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><cite id="CITEREFArnaut2021" class="citation book cs1">Arnaut, Luís G. (2021). <a rel="nofollow" class="external text" href="https://www.worldcat.org/title/on1063653763"><i>Chemical kinetics: from molecular structure to chemical reactivity</i></a> (Second ed.). Amsterdam, Netherlands ; Cambridge, MA: Elsevier. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0-444-64039-0</bdi>. <a href="OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/1063653763">1063653763</a>.</cite></span>

</li>

</ol></div></div>

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</style><div id="Basic_reaction_mechanisms264" style="font-size:114%;margin:0 4em">Basic <a href="Reaction_mechanism" title="Reaction mechanism">reaction mechanisms</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Nucleophilic_substitution" title="Nucleophilic substitution">Nucleophilic substitutions</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="SN1_reaction" title="SN1 reaction">Unimolecular nucleophilic substitution</a> (S<sub>N</sub>1)</li>

<li><a href="SN2_reaction" title="SN2 reaction">Bimolecular nucleophilic substitution</a> (S<sub>N</sub>2)</li>

<li><a href="SNi" title="SNi">Nucleophilic internal substitution</a> (S<sub>N</sub>i)</li>

<li><a href="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="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="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="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="E1cB-elimination_reaction" title="E1cB-elimination reaction">E1cB-elimination</a></li>

<li><a href="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="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="Electrophilic_addition" title="Electrophilic addition">Electrophilic addition</a> (A<sub>E</sub>)</li>

<li><a href="Nucleophilic_addition" title="Nucleophilic addition">Nucleophilic addition</a> (A<sub>N</sub>)</li>

<li><a href="Free-radical_addition" title="Free-radical addition">Free-radical addition</a></li>

<li><a href="Cycloaddition" title="Cycloaddition">Cycloaddition</a></li>

<li><a href="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="Intramolecular_reaction" title="Intramolecular reaction">Intramolecular reaction</a></li>

<li><a href="Photodissociation" title="Photodissociation">Photodissociation</a></li>

<li><a href="Lindemann_mechanism" title="Lindemann mechanism">Lindemann mechanism</a></li>

<li><a href="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="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="Redox" title="Redox">Redox</a></li>

<li><a href="Harpoon_reaction" title="Harpoon reaction">Harpoon reaction</a></li>

<li><a href="Grotthuss_mechanism" title="Grotthuss mechanism">Grotthuss mechanism</a></li>

<li><a href="Marcus_theory" title="Marcus theory">Marcus theory</a></li>

<li><a href="Inner_sphere_electron_transfer" title="Inner sphere electron transfer">Inner sphere electron transfer</a></li>

<li><a href="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="Solvent_effects" title="Solvent effects">Solvent effects</a></li>

<li><a href="Cage_effect" title="Cage effect">Cage effect</a></li>

<li><a href="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="Elementary_reaction" title="Elementary reaction">Elementary reaction</a></li>

<li><a href="Reaction_dynamics" title="Reaction dynamics">Reaction dynamics</a></li>

<li><a href="Reactive_intermediate" title="Reactive intermediate">Reactive intermediate</a></li>

<li><a href="Radical_(chemistry)" title="Radical (chemistry)">Radical (chemistry)</a></li>

<li><a href="Molecularity" title="Molecularity">Molecularity</a></li>

<li><a href="Stereochemistry" title="Stereochemistry">Stereochemistry</a></li>

<li><a href="Catalysis" title="Catalysis">Catalysis</a></li>

<li><a href="Collision_theory" title="Collision theory">Collision theory</a></li>

<li><a href="Arrow_pushing" title="Arrow pushing">Arrow pushing</a></li>

<li><a href="Potential_energy_surface" title="Potential energy surface">Potential energy surface</a></li>

<li><a href="More_O'Ferrall%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="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="Rate_equation" title="Rate equation">Rate equation</a></li>

<li><a href="Equilibrium_constant" title="Equilibrium constant">Equilibrium constant</a></li>

<li><a href="Rate-determining_step" title="Rate-determining step">Rate-determining step</a></li>

<li><a href="Reaction_coordinate" title="Reaction coordinate">Reaction coordinate</a></li>

<li><a href="Energy_profile_(chemistry)" title="Energy profile (chemistry)">Energy profile (chemistry)</a></li>

<li><a href="Transition_state_theory" title="Transition state theory">Transition state theory</a></li>

<li><a href="Activation_energy" title="Activation energy">Activation energy</a></li>

<li><a href="Activated_complex" title="Activated complex">Activated complex</a></li>

<li><a href="Arrhenius_equation" title="Arrhenius equation">Arrhenius equation</a></li>

<li><a href="Eyring_equation" title="Eyring equation">Eyring equation</a></li>

<li><a href="Michaelis%E2%80%93Menten_kinetics" title="Michaelis–Menten kinetics">Michaelis–Menten kinetics</a></li>

<li><a href="Diffusion-controlled_reaction" title="Diffusion-controlled reaction">Diffusion-controlled reaction</a></li></ul>

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