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mw-list-item"><a href="https://ca.wikipedia.org/wiki/Hom%C3%B2lisi" title="Homòlisi – Catalan" lang="ca" hreflang="ca" data-title="Homòlisi" 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/Homol%C3%BDza" title="Homolýza – Czech" lang="cs" hreflang="cs" data-title="Homolýza" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Homolysis_(cemeg)" title="Homolysis (cemeg) – Welsh" lang="cy" hreflang="cy" data-title="Homolysis (cemeg)" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Homolytische_Spaltung" title="Homolytische Spaltung – German" lang="de" hreflang="de" data-title="Homolytische Spaltung" 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/Homol%C3%BC%C3%BCs" title="Homolüüs – Estonian" lang="et" hreflang="et" data-title="Homolüüs" 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/Hom%C3%B3lisis" title="Homólisis – Spanish" lang="es" hreflang="es" data-title="Homólisis" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Homolisi" title="Homolisi – Basque" lang="eu" hreflang="eu" data-title="Homolisi" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%87%D9%85%E2%80%8C%DA%A9%D8%A7%D9%81%D8%AA" title="هم‌کافت – Persian" lang="fa" hreflang="fa" data-title="هم‌کافت" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Homolyse" title="Homolyse – French" lang="fr" hreflang="fr" data-title="Homolyse" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EA%B7%A0%ED%98%95_%EB%B6%84%ED%95%B4" title="균형 분해 – Korean" lang="ko" hreflang="ko" data-title="균형 분해" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Homoliza" title="Homoliza – Croatian" lang="hr" hreflang="hr" data-title="Homoliza" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%94%D7%95%D7%9E%D7%95%D7%9C%D7%99%D7%96%D7%94" title="הומוליזה – Hebrew" lang="he" hreflang="he" data-title="הומוליזה" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Homolytische_splitsing" title="Homolytische splitsing – Dutch" lang="nl" hreflang="nl" data-title="Homolytische splitsing" 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/%E3%83%9B%E3%83%A2%E3%83%AA%E3%82%B7%E3%82%B9" title="ホモリシス – Japanese" lang="ja" hreflang="ja" data-title="ホモリシス" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Ruptura_homol%C3%ADtica" title="Ruptura homolítica – Portuguese" lang="pt" hreflang="pt" data-title="Ruptura homolítica" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Homoliz%C4%83" title="Homoliză – Romanian" lang="ro" hreflang="ro" data-title="Homoliză" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Homoliza" title="Homoliza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Homoliza" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Homolys" title="Homolys – Swedish" lang="sv" hreflang="sv" data-title="Homolys" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li 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i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">For other uses, see <a href="/wiki/Homolysis_(disambiguation)" class="mw-redirect mw-disambig" title="Homolysis (disambiguation)">Homolysis (disambiguation)</a>.</div> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, <b>homolysis</b> (from <a href="/wiki/Greek_language" title="Greek language">Greek</a> <i> </i>ὅμοιος<i> (homoios)</i> 'equal' and <i> </i>λύσις<i> (lusis)</i> 'loosening') or <b>homolytic fission</b> is the dissociation of a <a href="/wiki/Molecular_bond" class="mw-redirect" title="Molecular bond">molecular bond</a> by a process where each of the fragments (an <a href="/wiki/Atom" title="Atom">atom</a> or <a href="/wiki/Molecule" title="Molecule">molecule</a>) retains one of the originally bonded <a href="/wiki/Electron" title="Electron">electrons</a>. During homolytic fission of a neutral molecule with an even number of electrons, two <a href="/wiki/Free-radical_halogenation" title="Free-radical halogenation">free radicals</a> will be generated.<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> That is, the two electrons involved in the original bond are distributed between the two fragment species. Bond cleavage is also possible by a process called <a href="/wiki/Heterolysis_(chemistry)" title="Heterolysis (chemistry)">heterolysis</a>. </p><p><span typeof="mw:File"><a href="/wiki/File:Homolysis_(Chemistry)_V.1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Homolysis_%28Chemistry%29_V.1.svg/350px-Homolysis_%28Chemistry%29_V.1.svg.png" decoding="async" width="350" height="46" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Homolysis_%28Chemistry%29_V.1.svg/525px-Homolysis_%28Chemistry%29_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Homolysis_%28Chemistry%29_V.1.svg/700px-Homolysis_%28Chemistry%29_V.1.svg.png 2x" data-file-width="469" data-file-height="61" /></a></span> </p><p>The energy involved in this process is called <a href="/wiki/Bond_dissociation_energy" class="mw-redirect" title="Bond dissociation energy">bond dissociation energy</a> (BDE).<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> BDE is defined as the "<a href="/wiki/Enthalpy" title="Enthalpy">enthalpy</a> (per <a href="/wiki/Mole_(unit)" title="Mole (unit)">mole</a>) required to break a given bond of some specific <a href="/wiki/Molecular_entity" title="Molecular entity">molecular entity</a> by homolysis," symbolized as <i><b>D</b></i>.<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> BDE is dependent on the <a href="/wiki/Bond_energy" title="Bond energy">strength</a> of the bond, which is determined by factors relating to the stability of the resulting <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical species</a>. </p><p>Because of the relatively high energy required to break bonds in this manner, homolysis occurs primarily under certain circumstances: </p> <ul><li>Light (i.e. <a href="/wiki/Ultraviolet" title="Ultraviolet">ultraviolet</a> radiation)</li></ul> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Homolysis2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Homolysis2.png/220px-Homolysis2.png" decoding="async" width="220" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Homolysis2.png/330px-Homolysis2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Homolysis2.png/440px-Homolysis2.png 2x" data-file-width="887" data-file-height="200" /></a><figcaption>The O-O σ bond in dibenzoyl peroxide is cleaved homolytically, distributing a radical to each benzoyloxy.</figcaption></figure> <ul><li>Heat <ul><li>Certain intramolecular bonds, such as the O–O bond of a <a href="/wiki/Peroxide" title="Peroxide">peroxide</a>, are sufficiently weak to spontaneously homolytically dissociate near room temperature.</li> <li>Most bonds homolyse at temperatures above 200°C.<sup id="cite_ref-foo_4-0" class="reference"><a href="#cite_note-foo-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li></ul></li></ul> <p><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a> is the <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a> which creates the <a href="/wiki/Deoxyadenosyl_radical" title="Deoxyadenosyl radical">deoxyadenosyl radical</a> by homolytic cleavage of a cobalt-carbon bond in reactions catalysed by <a href="/wiki/Methylmalonyl-CoA_mutase" title="Methylmalonyl-CoA mutase">methylmalonyl-CoA mutase</a>, <a href="/wiki/Isobutyryl-CoA_mutase" title="Isobutyryl-CoA mutase">isobutyryl-CoA mutase</a> and related enzymes. This triggers rearrangement reactions in the carbon framework of the substrates on which the enzymes act.<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-heading2"><h2 id="Factors_that_drive_homolysis">Factors that drive homolysis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Homolysis_(chemistry)&action=edit&section=1" title="Edit section: Factors that drive homolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Homolytic cleavage is driven by the ability of a molecule to absorb energy from light or heat, and the bond dissociation energy (<a href="/wiki/Enthalpy" title="Enthalpy">enthalpy</a>). If the radical species is better able to stabilize the free radical, the energy of the SOMO will be lowered, as will the bond dissociation energy. Bond dissociation energy is determined by multiple factors:<sup id="cite_ref-foo_4-1" class="reference"><a href="#cite_note-foo-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Homolysis_electronegativity.jpeg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Homolysis_electronegativity.jpeg/220px-Homolysis_electronegativity.jpeg" decoding="async" width="220" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Homolysis_electronegativity.jpeg/330px-Homolysis_electronegativity.jpeg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/17/Homolysis_electronegativity.jpeg/440px-Homolysis_electronegativity.jpeg 2x" data-file-width="488" data-file-height="298" /></a><figcaption>The bond dissociation energy depends on the electronegativity of the species bonded.</figcaption></figure> <ul><li><a href="/wiki/Electronegativity" title="Electronegativity">Electronegativity</a> <ul><li>Less electronegative atoms are better stabilizers of radicals, meaning that a bond between two electronegative atoms will have a higher BDE than a similar molecule with two less electronegative atoms.<sup id="cite_ref-foo_4-2" class="reference"><a href="#cite_note-foo-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li></ul></li> <li><a href="/wiki/Polarizability" title="Polarizability">Polarizability</a> <ul><li>The larger the electron cloud, the better an atom can stabilize the radical (i.e. Iodine is very polarizable and a radical stabilizer).<sup id="cite_ref-foo_4-3" class="reference"><a href="#cite_note-foo-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li></ul></li></ul> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Hybridation_sp3-anim_100.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Hybridation_sp3-anim_100.gif/220px-Hybridation_sp3-anim_100.gif" decoding="async" width="220" height="114" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Hybridation_sp3-anim_100.gif/330px-Hybridation_sp3-anim_100.gif 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/Hybridation_sp3-anim_100.gif/440px-Hybridation_sp3-anim_100.gif 2x" data-file-width="667" data-file-height="346" /></a><figcaption>An sp3 hybridized atom is the most stable configuration for a radical because of the low s-character.</figcaption></figure> <ul><li><a href="/wiki/Orbital_hybridization" class="mw-redirect" title="Orbital hybridization">Orbital hybridization</a> <ul><li>The s-character of an orbital relates to how close electrons are to the nucleus. In the case of a radical, s-character more specifically relates to how close the single electron is to the nucleus. Radicals decrease in stability as they are closer to the nucleus, because the electron affinity of the orbital increases. As a general rule, hybridizations minimizing s-character increase the stability of radicals, and decreases the bond dissociation energy (i.e. sp<sup>3</sup> hybridization is most stabilizing).<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></li></ul></li></ul> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Bromine-dioxide-radical-resonance-2D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Bromine-dioxide-radical-resonance-2D.png/220px-Bromine-dioxide-radical-resonance-2D.png" decoding="async" width="220" height="47" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Bromine-dioxide-radical-resonance-2D.png/330px-Bromine-dioxide-radical-resonance-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/72/Bromine-dioxide-radical-resonance-2D.png/440px-Bromine-dioxide-radical-resonance-2D.png 2x" data-file-width="2150" data-file-height="461" /></a><figcaption>This bromine dioxide radical is stabilized by the resonance of the molecule. Structure from J. Chem. Phys. (1997) 107, 8292-8302.<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></figcaption></figure> <ul><li><a href="/wiki/Resonance" title="Resonance">Resonance</a> <ul><li>Radicals can be stabilized by the donation of negative charge from resonance, or in other words, <a href="/wiki/Electron_delocalization" class="mw-redirect" title="Electron delocalization">electron delocalization</a>.</li></ul></li> <li><a href="/wiki/Hyperconjugation" title="Hyperconjugation">Hyperconjugation</a> <ul><li>Carbon radicals are stabilized by hyperconjugation, meaning that more substituted carbons are more stable, and hence have lower BDEs.</li> <li>In 2005, Gronert proposed an alternative hypothesis involving the relief of substituent group <a href="/wiki/Steric_strain" class="mw-redirect" title="Steric strain">steric strain</a> (as opposed to the before accepted paradigm, which suggests that carbon radicals are stabilized via alkyl groups).<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></li></ul></li></ul> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Radical_stability_substitution.jpeg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Radical_stability_substitution.jpeg/220px-Radical_stability_substitution.jpeg" decoding="async" width="220" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Radical_stability_substitution.jpeg/330px-Radical_stability_substitution.jpeg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Radical_stability_substitution.jpeg/440px-Radical_stability_substitution.jpeg 2x" data-file-width="492" data-file-height="180" /></a><figcaption>The most substituted carbon radical is the most stable.</figcaption></figure> <ul><li>The <a href="/wiki/Captodative_Effect" class="mw-redirect" title="Captodative Effect">captodative effect</a> <ul><li>Radicals can be stabilized by a synergistic effect of both <a href="/wiki/Electron-withdrawing_group" title="Electron-withdrawing group">electron-withdrawing group</a> and <a href="/wiki/Electron-donating_group" class="mw-redirect" title="Electron-donating group">electron-donating group</a> substituents.</li> <li>Electron-withdrawing groups often contain empty π* orbitals that are low in energy and overlap with the SOMO, creating two new orbitals: one that is lower in energy and stabilizing to the radical, and an empty higher energy orbital. Similarly, electron-donating orbitals combine with the radical SOMO, allowing a lone pair to lower in energy and the radical to enter the new higher energy orbital. This interaction is net stabilizing.<sup id="cite_ref-foo_4-4" class="reference"><a href="#cite_note-foo-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li></ul></li></ul> <p><br /> </p> <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=Homolysis_(chemistry)&action=edit&section=2" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Alpha_cleavage" title="Alpha cleavage">Alpha cleavage</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=Homolysis_(chemistry)&action=edit&section=3" 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. 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Chalk. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-9678550-9-8" title="Special:BookSources/0-9678550-9-8">0-9678550-9-8</a>. <a rel="nofollow" class="external free" href="https://doi.org/10.1351/goldbook">https://doi.org/10.1351/goldbook</a>.</span> </li> <li id="cite_note-foo-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-foo_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-foo_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-foo_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-foo_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-foo_4-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text">Clayden, Jonathan, Greeves, Nick, Warren, Stuart. (2012). Organic Chemistry (Second ed.). 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(1997-11-22). <a rel="nofollow" class="external text" href="https://pubs.aip.org/jcp/article/107/20/8292/478420/The-rotational-spectrum-and-molecular-properties">"The rotational spectrum and molecular properties of bromine dioxide, OBrO"</a>. <i>The Journal of Chemical Physics</i>. <b>107</b> (20): 8292–8302. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1063%2F1.475030">10.1063/1.475030</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Chemical+Physics&rft.atitle=The+rotational+spectrum+and+molecular+properties+of+bromine+dioxide%2C+OBrO&rft.volume=107&rft.issue=20&rft.pages=8292-8302&rft.date=1997-11-22&rft_id=info%3Adoi%2F10.1063%2F1.475030&rft.aulast=M%C3%BCller&rft.aufirst=Holger+S.+P.&rft.au=Miller%2C+Charles+E.&rft.au=Cohen%2C+Edward+A.&rft_id=https%3A%2F%2Fpubs.aip.org%2Fjcp%2Farticle%2F107%2F20%2F8292%2F478420%2FThe-rotational-spectrum-and-molecular-properties&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHomolysis+%28chemistry%29" 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="CITEREFGronert2006" class="citation journal cs1">Gronert, Scott (2006-02-01). <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/10.1021/jo052363t">"An Alternative Interpretation of the C−H Bond Strengths of Alkanes"</a>. <i>The Journal of Organic Chemistry</i>. <b>71</b> (3): 1209–1219. <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%2Fjo052363t">10.1021/jo052363t</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=An+Alternative+Interpretation+of+the+C%E2%88%92H+Bond+Strengths+of+Alkanes&rft.volume=71&rft.issue=3&rft.pages=1209-1219&rft.date=2006-02-01&rft_id=info%3Adoi%2F10.1021%2Fjo052363t&rft.aulast=Gronert&rft.aufirst=Scott&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2F10.1021%2Fjo052363t&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHomolysis+%28chemistry%29" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style 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href="/wiki/Intramolecular_force" title="Intramolecular force">Intramolecular</a><br />(strong)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Covalent_bond" title="Covalent bond">Covalent</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electron_deficiency" title="Electron deficiency">Electron deficiency</a> <ul><li><a href="/wiki/Three-center_two-electron_bond" title="Three-center two-electron bond">3c–2e</a></li> <li><a href="/wiki/Four-center_two-electron_bond" title="Four-center two-electron bond">4c–2e</a></li> <li><a href="/wiki/Eight-center_two-electron_bond" class="mw-redirect" title="Eight-center two-electron bond">8c–2e</a></li></ul></li> <li><a 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style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/File:Ligatio-covalens.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/200px-Ligatio-covalens.svg.png" decoding="async" width="200" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/300px-Ligatio-covalens.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/400px-Ligatio-covalens.svg.png 2x" data-file-width="597" data-file-height="265" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Chemfm_carbon_monoxide_3_1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/200px-Chemfm_carbon_monoxide_3_1.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/300px-Chemfm_carbon_monoxide_3_1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/400px-Chemfm_carbon_monoxide_3_1.svg.png 2x" data-file-width="99" data-file-height="56" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Pi-Bond.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/200px-Pi-Bond.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/300px-Pi-Bond.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/400px-Pi-Bond.svg.png 2x" data-file-width="1920" data-file-height="1080" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intermolecular_force" title="Intermolecular force">Intermolecular</a><br />(weak)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Van_der_Waals_force" title="Van der Waals force">Van der Waals<br />forces</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/London_dispersion_force" title="London dispersion force">London dispersion</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_bond" title="Hydrogen bond">Hydrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Low-barrier_hydrogen_bond" title="Low-barrier hydrogen bond">Low-barrier</a></li> <li><a href="/wiki/Resonance-assisted_hydrogen_bond" class="mw-redirect" title="Resonance-assisted hydrogen bond">Resonance-assisted</a></li> <li><a href="/wiki/Symmetric_hydrogen_bond" title="Symmetric hydrogen bond">Symmetric</a></li> <li><a href="/wiki/Dihydrogen_bond" title="Dihydrogen bond">Dihydrogen bonds</a></li> <li><a href="/wiki/C%E2%80%93H%C2%B7%C2%B7%C2%B7O_interaction" title="C–H···O interaction">C–H···O interaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Non-covalent_interactions" class="mw-redirect" title="Non-covalent interactions">Noncovalent</a><br />other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mechanically_interlocked_molecular_architectures" title="Mechanically interlocked molecular architectures">Mechanical</a></li> <li><a href="/wiki/Halogen_bond" title="Halogen bond">Halogen</a></li> <li><a href="/wiki/Chalcogen_bond" title="Chalcogen bond">Chalcogen</a></li> <li><a href="/wiki/Metallophilic_interaction" title="Metallophilic interaction">Metallophilic</a> (<a href="/wiki/Aurophilicity" title="Aurophilicity">aurophilic</a>)</li> <li><a href="/wiki/Intercalation_(chemistry)" title="Intercalation (chemistry)">Intercalation</a></li> <li><a href="/wiki/Stacking_(chemistry)" title="Stacking (chemistry)">Stacking</a></li> <li><a href="/wiki/Cation%E2%80%93pi_interaction" class="mw-redirect" title="Cation–pi interaction">Cation–pi</a></li> <li><a href="/wiki/Cation%E2%80%93pi_interaction#Anion–π_interaction" class="mw-redirect" title="Cation–pi interaction">Anion–pi</a></li> <li><a href="/wiki/Salt_bridge_(protein_and_supramolecular)" title="Salt bridge (protein and supramolecular)">Salt bridge</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bond_cleavage" title="Bond cleavage">Bond cleavage</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/Heterolysis_(chemistry)" title="Heterolysis (chemistry)">Heterolysis</a></li> <li><a class="mw-selflink selflink">Homolysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Electron_counting" title="Electron counting">Electron counting</a> rules</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/Aromaticity" title="Aromaticity">Aromaticity</a> <ul><li><a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a></li> <li><a href="/wiki/Baird%27s_rule" title="Baird's rule">Baird's rule</a></li> <li><a href="/wiki/M%C3%B6bius_aromaticity" title="Möbius aromaticity">Möbius</a></li> <li><a href="/wiki/Spherical_aromaticity" title="Spherical aromaticity">spherical</a></li></ul></li> <li><a href="/wiki/Polyhedral_skeletal_electron_pair_theory" title="Polyhedral skeletal electron pair theory">Polyhedral skeletal electron pair theory</a></li> <li><a href="/wiki/Jemmis_mno_rules" title="Jemmis mno rules">Jemmis mno rules</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" href="https://en.wikipedia.org/w/index.php?title=Homolysis_(chemistry)&oldid=1249449365">https://en.wikipedia.org/w/index.php?title=Homolysis_(chemistry)&oldid=1249449365</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Category</a>: <ul><li><a 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