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Saturated and unsaturated compounds - Wikipedia

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compounds" 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-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%A8%E0%AE%BF%E0%AE%B1%E0%AF%88%E0%AE%B5%E0%AF%81%E0%AE%B1%E0%AF%8D%E0%AE%B1_%E0%AE%AE%E0%AE%B1%E0%AF%8D%E0%AE%B1%E0%AF%81%E0%AE%AE%E0%AF%8D_%E0%AE%A8%E0%AE%BF%E0%AE%B1%E0%AF%88%E0%AE%B5%E0%AF%81%E0%AE%B1%E0%AE%BE%E0%AE%A4_%E0%AE%9A%E0%AF%87%E0%AE%B0%E0%AF%8D%E0%AE%AE%E0%AE%99%E0%AF%8D%E0%AE%95%E0%AE%B3%E0%AF%8D" title="நிறைவுற்ற மற்றும் நிறைவுறாத சேர்மங்கள் – Tamil" lang="ta" hreflang="ta" data-title="நிறைவுற்ற மற்றும் நிறைவுறாத சேர்மங்கள்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a 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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"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Unsaturated_hydrocarbon&amp;redirect=no" class="mw-redirect" title="Unsaturated hydrocarbon">Unsaturated hydrocarbon</a>)</span></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">Classification of organic compounds based on nature of their chemical bonds</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote 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">This article is about chemical bonds. For saturation status of solutions, see <a href="/wiki/Solubility" title="Solubility">solubility</a> and <a href="/wiki/Supersaturation" title="Supersaturation">supersaturation</a>.</div> <p>A <b>saturated compound</b> is a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> (or ion) that resists <a href="/wiki/Addition_reaction" title="Addition reaction">addition reactions</a>, such as <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a>, <a href="/wiki/Oxidative_addition" title="Oxidative addition">oxidative addition</a>, and binding of a <a href="/wiki/Lewis_acids_and_bases" title="Lewis acids and bases">Lewis base</a>. The term is used in many contexts and for many classes of chemical compounds. Overall, saturated compounds are less reactive than unsaturated compounds. Saturation is derived from the Latin word <i>saturare</i>, meaning 'to fill'.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Organic_chemistry">Organic chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Saturated_and_unsaturated_compounds&amp;action=edit&amp;section=1" title="Edit section: Organic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Generally distinct types of unsaturated organic compounds are recognized. For hydrocarbons: </p> <ul><li><a href="/wiki/Alkene" title="Alkene">alkene</a> (unsaturated) vs alkane (saturated)</li> <li><a href="/wiki/Alkyne" title="Alkyne">alkyne</a> (unsaturated) vs alkane (saturated)</li> <li><a href="/wiki/Arene" class="mw-redirect" title="Arene">arene</a> (unsaturated) vs cycloalkane (saturated)</li></ul> <p>For organic compounds containing heteroatoms (other than C and H), the list of unsaturated groups is long but some common types are: </p> <ul><li><a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a>, e.g. <a href="/wiki/Ketone" title="Ketone">ketones</a>, <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a>, <a href="/wiki/Ester" title="Ester">esters</a>, <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> (unsaturated) vs alcohol or ether (saturated)</li> <li><a href="/wiki/Nitrile" title="Nitrile">nitrile</a> (unsaturated) vs amine (saturated)</li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">nitro</a> (unsaturated) vs amine (saturated)</li></ul> <table class="wikitable floatleft" style="text-align:center"> <tbody><tr> <th colspan="3">Saturated compounds </th></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Ethan_Lewis.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Ethan_Lewis.svg/102px-Ethan_Lewis.svg.png" decoding="async" width="102" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/35/Ethan_Lewis.svg/153px-Ethan_Lewis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/35/Ethan_Lewis.svg/204px-Ethan_Lewis.svg.png 2x" data-file-width="142" data-file-height="107" /></a></span> <p><a href="/wiki/Ethane" title="Ethane">Ethane</a> </p> </td> <td><span typeof="mw:File"><a href="/wiki/File:Propan_Lewis.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Propan_Lewis.svg/136px-Propan_Lewis.svg.png" decoding="async" width="136" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Propan_Lewis.svg/204px-Propan_Lewis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Propan_Lewis.svg/272px-Propan_Lewis.svg.png 2x" data-file-width="182" data-file-height="107" /></a></span> <p><a href="/wiki/Propane" title="Propane">Propane</a> </p> </td> <td><span typeof="mw:File"><a href="/wiki/File:Octan-1-ol_Skelett.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Octan-1-ol_Skelett.svg/245px-Octan-1-ol_Skelett.svg.png" decoding="async" width="245" height="32" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Octan-1-ol_Skelett.svg/368px-Octan-1-ol_Skelett.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Octan-1-ol_Skelett.svg/490px-Octan-1-ol_Skelett.svg.png 2x" data-file-width="344" data-file-height="45" /></a></span> <p><a href="/wiki/1-Octanol" title="1-Octanol">1-Octanol</a> </p> </td></tr></tbody></table> <table class="wikitable floatcenter" style="text-align:center; font-size:89"> <tbody><tr> <th colspan="3">Unsaturated compounds </th></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Ethene_structural.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ethene_structural.svg/83px-Ethene_structural.svg.png" decoding="async" width="83" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ethene_structural.svg/125px-Ethene_structural.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ethene_structural.svg/166px-Ethene_structural.svg.png 2x" data-file-width="170" data-file-height="160" /></a></span> <p><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a> </p> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ethyne-2D-flat.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Ethyne-2D-flat.png/111px-Ethyne-2D-flat.png" decoding="async" width="111" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Ethyne-2D-flat.png/167px-Ethyne-2D-flat.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/28/Ethyne-2D-flat.png/222px-Ethyne-2D-flat.png 2x" data-file-width="1100" data-file-height="238" /></a></span> <p><a href="/wiki/Acetylene" title="Acetylene">Acetylene</a> </p> </td> <td><span typeof="mw:File"><a href="/wiki/File:Alpha-Linolenic_acid_Structural_Formulae_V.2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Alpha-Linolenic_acid_Structural_Formulae_V.2.svg/183px-Alpha-Linolenic_acid_Structural_Formulae_V.2.svg.png" decoding="async" width="183" height="221" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Alpha-Linolenic_acid_Structural_Formulae_V.2.svg/275px-Alpha-Linolenic_acid_Structural_Formulae_V.2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Alpha-Linolenic_acid_Structural_Formulae_V.2.svg/366px-Alpha-Linolenic_acid_Structural_Formulae_V.2.svg.png 2x" data-file-width="366" data-file-height="441" /></a></span> <p><a href="/wiki/Alpha-Linolenic_acid" class="mw-redirect" title="Alpha-Linolenic acid"><i>alpha</i>-Linolenic acid</a>, an unsaturated fatty acid </p> </td></tr></tbody></table> <p>Unsaturated compounds generally carry out typical addition reactions that are not possible with saturated compounds such as alkanes. A saturated organic compound has only single bonds between carbon atoms. An important class of saturated compounds are the <a href="/wiki/Alkane" title="Alkane">alkanes</a>. Many saturated compounds have functional groups, e.g., <a href="/wiki/Alcohols" class="mw-redirect" title="Alcohols">alcohols</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Unsaturated_organic_compounds">Unsaturated organic compounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Saturated_and_unsaturated_compounds&amp;action=edit&amp;section=2" title="Edit section: Unsaturated organic compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The concept of saturation can be described using various naming systems, <a href="/wiki/Formula" title="Formula">formulas</a>, and <a href="/wiki/Analytical_chemistry" title="Analytical chemistry">analytical tests</a>. For instance, <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">IUPAC nomenclature</a> is a system of naming conventions used to describe the type and location of unsaturation within organic compounds. The "<a href="/wiki/Degree_of_unsaturation" title="Degree of unsaturation">degree of unsaturation</a>" is a <a href="/wiki/Formula" title="Formula">formula</a> used to summarize and diagram the amount of hydrogen that a compound can bind. Unsaturation can be determined by <a href="/wiki/NMR" class="mw-redirect" title="NMR">NMR</a>, <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a>, and <a href="/wiki/IR_spectroscopy" class="mw-redirect" title="IR spectroscopy">IR spectroscopy</a>, or by determining a compound's <a href="/wiki/Bromine_number" title="Bromine number">bromine number</a> or <a href="/wiki/Iodine_number" class="mw-redirect" title="Iodine number">iodine number</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fatty_acids_and_fats">Fatty acids and fats</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Saturated_and_unsaturated_compounds&amp;action=edit&amp;section=3" title="Edit section: Fatty acids and fats"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:TriglycerideTallow.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/TriglycerideTallow.svg/340px-TriglycerideTallow.svg.png" decoding="async" width="340" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/TriglycerideTallow.svg/510px-TriglycerideTallow.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/TriglycerideTallow.svg/680px-TriglycerideTallow.svg.png 2x" data-file-width="512" data-file-height="214" /></a><figcaption>The bottom chain of this fat is unsaturated.</figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Unsaturated_fat" title="Unsaturated fat">Unsaturated fat</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Hydrogenation#Food_industry" title="Hydrogenation">Hydrogenation §&#160;Food industry</a></div> <p>The terms saturated vs unsaturated are often applied to the <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acid</a> constituents of <a href="/wiki/Fat" title="Fat">fats</a>. The triglycerides (fats) that comprise <a href="/wiki/Tallow" title="Tallow">tallow</a> are derived from the saturated <a href="/wiki/Stearic_acid" title="Stearic acid">stearic</a> and monounsaturated <a href="/wiki/Oleic_acid" title="Oleic acid">oleic acids</a>.<sup id="cite_ref-Ullmann_3-0" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> Many <a href="/wiki/Vegetable_oil" title="Vegetable oil">vegetable oils</a> contain fatty acids with one (<i>monounsaturated</i>) or more (<i>polyunsaturated</i>) double bonds in them. </p> <div class="mw-heading mw-heading2"><h2 id="Saturated_and_unsaturated_compounds_beyond_organic_chemistry">Saturated and unsaturated compounds beyond organic chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Saturated_and_unsaturated_compounds&amp;action=edit&amp;section=4" title="Edit section: Saturated and unsaturated compounds beyond organic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Organometallic_chemistry">Organometallic chemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Saturated_and_unsaturated_compounds&amp;action=edit&amp;section=5" title="Edit section: Organometallic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Vaska%27s.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Vaska%27s.svg/220px-Vaska%27s.svg.png" decoding="async" width="220" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Vaska%27s.svg/330px-Vaska%27s.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Vaska%27s.svg/440px-Vaska%27s.svg.png 2x" data-file-width="116" data-file-height="74" /></a><figcaption><a href="/wiki/Vaska%27s_complex" title="Vaska&#39;s complex">IrCl(CO)(PPh3)2</a> is an unsaturated <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complex</a>.</figcaption></figure> <p>In <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>, a coordinatively unsaturated complex has fewer than <a href="/wiki/18-electron_rule" title="18-electron rule">18 valence electrons</a> and thus is susceptible to <a href="/wiki/Oxidative_addition" title="Oxidative addition">oxidative addition</a> or coordination of an additional <a href="/wiki/Ligand" title="Ligand">ligand</a>. Unsaturation is characteristic of many <a href="/wiki/Catalysis" title="Catalysis">catalysts</a>. The opposite of coordinatively unsaturated is coordinatively saturated. Complexes that are coordinatively saturated rarely exhibit catalytic properties.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Surfaces">Surfaces</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Saturated_and_unsaturated_compounds&amp;action=edit&amp;section=6" title="Edit section: Surfaces"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Surface_science" title="Surface science">Surface science</a></div> <p>In <a href="/wiki/Physical_chemistry" title="Physical chemistry">physical chemistry</a>, when referring to surface processes, saturation denotes the degree at which a binding site is fully occupied. For example, <a href="/wiki/Cation-exchange_capacity" title="Cation-exchange capacity">base saturation</a> refers to the fraction of <a href="/wiki/Cation-exchange_capacity" title="Cation-exchange capacity">exchangeable cations</a> that are base cations. </p> <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=Saturated_and_unsaturated_compounds&amp;action=edit&amp;section=7" 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"><i><a href="/wiki/Mosby%27s_Medical,_Nursing_%26_Allied_Health_Dictionary" class="mw-redirect" title="Mosby&#39;s Medical, Nursing &amp; Allied Health Dictionary">Mosby's Medical, Nursing &amp; Allied Health Dictionary</a></i>, Fourth Edition, Mosby-Year Book Inc., 1994, p. 1394</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"><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><cite id="CITEREFSmith,_Michael_B.March,_Jerry2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&amp;printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th&#160;ed.), New York: Wiley-Interscience, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&amp;rft.place=New+York&amp;rft.edition=6th&amp;rft.pub=Wiley-Interscience&amp;rft.date=2007&amp;rft.isbn=978-0-471-72091-1&amp;rft.au=Smith%2C+Michael+B.&amp;rft.au=March%2C+Jerry&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ASaturated+and+unsaturated+compounds" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ullmann_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAlfred_Thomas2002" class="citation encyclopaedia cs1">Alfred Thomas (2002). "Fats and Fatty Oils". <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.a10_173">10.1002/14356007.a10_173</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/3527306730" title="Special:BookSources/3527306730"><bdi>3527306730</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Fats+and+Fatty+Oils&amp;rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&amp;rft.place=Weinheim&amp;rft.pub=Wiley-VCH&amp;rft.date=2002&amp;rft_id=info%3Adoi%2F10.1002%2F14356007.a10_173&amp;rft.isbn=3527306730&amp;rft.au=Alfred+Thomas&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ASaturated+and+unsaturated+compounds" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text">Hartwig, J. F. <i>Organotransition Metal Chemistry, from Bonding to Catalysis</i>; University Science Books: New York, 2010. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/1-891389-53-X" title="Special:BookSources/1-891389-53-X">1-891389-53-X</a></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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://goldbook.iupac.org/html/C/C01334.html">"IUPAC definition of Coordinatively Unsaturated Complex"</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.C01334">10.1351/goldbook.C01334</a></span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=IUPAC+definition+of+Coordinatively+Unsaturated+Complex&amp;rft_id=info%3Adoi%2F10.1351%2Fgoldbook.C01334&amp;rft_id=https%3A%2F%2Fgoldbook.iupac.org%2Fhtml%2FC%2FC01334.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ASaturated+and+unsaturated+compounds" class="Z3988"></span></span> </li> </ol></div></div> <!-- NewPP limit report Parsed by mw‐web.codfw.main‐f69cdc8f6‐kgm48 Cached time: 20241122145809 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.221 seconds Real time usage: 0.290 seconds Preprocessor visited node count: 710/1000000 Post‐expand include size: 9884/2097152 bytes Template argument size: 1019/2097152 bytes Highest expansion depth: 16/100 Expensive parser function count: 6/500 Unstrip recursion depth: 1/20 Unstrip post‐expand size: 16221/5000000 bytes Lua time usage: 0.128/10.000 seconds Lua memory usage: 4135567/52428800 bytes Number of Wikibase entities loaded: 0/400 --> <!-- Transclusion expansion time report (%,ms,calls,template) 100.00% 251.857 1 -total 54.38% 136.953 1 Template:Reflist 35.34% 89.002 1 Template:March6th 28.96% 72.936 1 Template:Short_description 16.39% 41.284 2 Template:Pagetype 9.69% 24.399 1 Template:About 7.34% 18.495 4 Template:Main_other 6.94% 17.481 1 Template:ISBN 6.29% 15.846 1 Template:SDcat 3.98% 10.022 1 Template:Catalog_lookup_link --> <!-- Saved in parser cache with key enwiki:pcache:idhash:1786805-0!canonical and timestamp 20241122145809 and revision id 1251408341. 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