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class="vector-toc-numb">2</span> <span>In nature</span> </div> </a> <ul id="toc-In_nature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Applications</span> </div> </a> <button aria-controls="toc-Applications-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Applications subsection</span> </button> <ul id="toc-Applications-sublist" class="vector-toc-list"> <li id="toc-Animal_feed_additives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Animal_feed_additives"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Animal feed additives</span> </div> </a> <ul id="toc-Animal_feed_additives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dental_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dental_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Dental use</span> </div> </a> <ul id="toc-Dental_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chelation_therapy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chelation_therapy"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Chelation therapy</span> </div> </a> <ul id="toc-Chelation_therapy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Contrast_agents" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Contrast_agents"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Contrast agents</span> </div> </a> <ul id="toc-Contrast_agents-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nutritional_advantages_and_issues" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nutritional_advantages_and_issues"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Nutritional advantages and issues</span> </div> </a> <ul id="toc-Nutritional_advantages_and_issues-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cleaning_and_water_softening" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cleaning_and_water_softening"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.6</span> <span>Cleaning and water softening</span> </div> </a> <ul id="toc-Cleaning_and_water_softening-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fertilizers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fertilizers"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.7</span> <span>Fertilizers</span> </div> </a> <ul id="toc-Fertilizers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Economic_situation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Economic_situation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.8</span> <span>Economic situation</span> </div> </a> <ul id="toc-Economic_situation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reversal" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reversal"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Reversal</span> </div> </a> <ul id="toc-Reversal-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" 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<div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 34 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-34" 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">34 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Chelasie" title="Chelasie – Afrikaans" lang="af" hreflang="af" data-title="Chelasie" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%D8%AE%D9%84%D8%A7%D8%A8" title="استخلاب – Arabic" lang="ar" hreflang="ar" data-title="استخلاب" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Helacija" title="Helacija – Bosnian" lang="bs" hreflang="bs" data-title="Helacija" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Chelatace" title="Chelatace – Czech" lang="cs" hreflang="cs" data-title="Chelatace" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Kelaatumine" title="Kelaatumine – Estonian" lang="et" hreflang="et" data-title="Kelaatumine" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A7%CE%B7%CE%BB%CE%B9%CE%BA%CE%BF%CF%80%CE%BF%CE%AF%CE%B7%CF%83%CE%B7" title="Χηλικοποίηση – Greek" lang="el" hreflang="el" data-title="Χηλικοποίηση" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Agente_quelante" title="Agente quelante – Spanish" lang="es" hreflang="es" data-title="Agente quelante" 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/Kelato" title="Kelato – Basque" lang="eu" hreflang="eu" data-title="Kelato" 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/%DA%86%D9%86%DA%AF%D8%A7%D9%84%D8%B4" title="چنگالش – Persian" lang="fa" hreflang="fa" data-title="چنگالش" 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/Ch%C3%A9lation" title="Chélation – French" lang="fr" hreflang="fr" data-title="Chélation" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gu mw-list-item"><a href="https://gu.wikipedia.org/wiki/%E0%AA%9A%E0%AB%87%E0%AA%B2%E0%AB%87%E0%AA%B6%E0%AA%A8" title="ચેલેશન – Gujarati" lang="gu" hreflang="gu" data-title="ચેલેશન" data-language-autonym="ગુજરાતી" data-language-local-name="Gujarati" class="interlanguage-link-target"><span>ગુજરાતી</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%82%AC%EB%A0%88%EC%9D%B4%ED%8A%B8" title="킬레이트 – Korean" lang="ko" hreflang="ko" data-title="킬레이트" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%95%E0%A5%87%E0%A4%B2%E0%A5%87%E0%A4%B6%E0%A4%A8" title="केलेशन – Hindi" lang="hi" hreflang="hi" data-title="केलेशन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Kel-ionuro" title="Kel-ionuro – Ido" lang="io" hreflang="io" data-title="Kel-ionuro" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Pengelatan" title="Pengelatan – Indonesian" lang="id" hreflang="id" data-title="Pengelatan" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Chelazione" title="Chelazione – Italian" lang="it" hreflang="it" data-title="Chelazione" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%9B%D7%9C%D7%A6%D7%99%D7%94" title="כלציה – Hebrew" lang="he" hreflang="he" data-title="כלציה" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%B0%E1%83%94%E1%83%9A%E1%83%90%E1%83%A2%E1%83%94%E1%83%91%E1%83%98" title="ჰელატები – Georgian" lang="ka" hreflang="ka" data-title="ჰელატები" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Kel%C3%A1that%C3%A1s" title="Keláthatás – Hungarian" lang="hu" hreflang="hu" data-title="Keláthatás" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Chelatie" title="Chelatie – Dutch" lang="nl" hreflang="nl" data-title="Chelatie" 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%82%AD%E3%83%AC%E3%83%BC%E3%83%88" title="キレート – Japanese" lang="ja" hreflang="ja" data-title="キレート" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Kompleksdanninger" title="Kompleksdanninger – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Kompleksdanninger" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Chelatacja" title="Chelatacja – Polish" lang="pl" hreflang="pl" data-title="Chelatacja" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Efeito_quelato" title="Efeito quelato – Portuguese" lang="pt" hreflang="pt" data-title="Efeito quelato" 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/Chelare" title="Chelare – Romanian" lang="ro" hreflang="ro" data-title="Chelare" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Chelation" title="Chelation – Simple English" lang="en-simple" hreflang="en-simple" data-title="Chelation" 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/Chel%C3%A1cia" title="Chelácia – Slovak" lang="sk" hreflang="sk" data-title="Chelácia" 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/Kelacija" title="Kelacija – Slovenian" lang="sl" hreflang="sl" data-title="Kelacija" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Helacija" title="Helacija – Serbian" lang="sr" hreflang="sr" data-title="Helacija" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Helacija" title="Helacija – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Helacija" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Kelaatio" title="Kelaatio – Finnish" lang="fi" hreflang="fi" data-title="Kelaatio" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%84%E0%B8%B5%E0%B9%80%E0%B8%A5%E0%B8%8A%E0%B8%B1%E0%B8%99" title="คีเลชัน – Thai" lang="th" hreflang="th" data-title="คีเลชัน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/%C5%9Eelatlama" title="Şelatlama – Turkish" lang="tr" hreflang="tr" data-title="Şelatlama" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%9E%AF%E5%90%88%E7%89%A9" title="螯合物 – Chinese" lang="zh" hreflang="zh" data-title="螯合物" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit 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.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 sequestering agents in general. For chemicals used in food processing, see <a href="/wiki/Sequestrant" title="Sequestrant">sequestrant</a>. For the isopod genus, see <a href="/wiki/Chelator_(crustacean)" title="Chelator (crustacean)">Chelator (crustacean)</a>.</div> <p><b>Chelation</b> is a type of bonding of <a href="/wiki/Ions" class="mw-redirect" title="Ions">ions</a> and their molecules to metal ions. It involves the formation or presence of two or more separate <a href="/wiki/Coordinate_bond" class="mw-redirect" title="Coordinate bond">coordinate bonds</a> between a <a href="/wiki/Denticity" title="Denticity">polydentate</a> (multiple bonded) <a href="/wiki/Ligand" title="Ligand">ligand</a> and a single central metal atom.<sup id="cite_ref-IUPAC_1-0" class="reference"><a href="#cite_note-IUPAC-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><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> These ligands are called chelants, chelators, chelating agents, or sequestering agents. They are usually <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a>, but this is not a necessity. </p><p>The word <i>chelation</i> is derived from <a href="/wiki/Greek_language" title="Greek language">Greek</a> χηλή, <i>chēlē</i>, meaning "claw"; the ligands lie around the central atom like the claws of a <a href="/wiki/Crab" title="Crab">crab</a>. The term <i>chelate</i> was first applied in 1920 by Sir Gilbert T. Morgan and H. D. K. Drew, who stated: "The adjective chelate, derived from the great claw or <i>chele</i> (Greek) of the crab or other crustaceans, is suggested for the caliperlike groups which function as two associating units and fasten to the central atom so as to produce <a href="/wiki/Heterocyclic" class="mw-redirect" title="Heterocyclic">heterocyclic</a> rings."<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><p>Chelation is useful in applications such as providing nutritional supplements, in <a href="/wiki/Chelation_therapy" title="Chelation therapy">chelation therapy</a> to remove toxic metals from the body, as <a href="/wiki/Contrast_medium" class="mw-redirect" title="Contrast medium">contrast agents</a> in <a href="/wiki/MRI" class="mw-redirect" title="MRI">MRI scanning</a>, in manufacturing using <a href="/wiki/Homogeneous_catalyst" class="mw-redirect" title="Homogeneous catalyst">homogeneous catalysts</a>, in chemical <a href="/wiki/Water_treatment" title="Water treatment">water treatment</a> to assist in the removal of metals, and in <a href="/wiki/Fertilizer" title="Fertilizer">fertilizers</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Chelate_effect">Chelate effect</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=1" title="Edit section: Chelate effect"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Me-EN.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Me-EN.svg/220px-Me-EN.svg.png" decoding="async" width="220" height="159" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Me-EN.svg/330px-Me-EN.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/88/Me-EN.svg/440px-Me-EN.svg.png 2x" data-file-width="87" data-file-height="63" /></a><figcaption><a href="/wiki/Ethylenediamine" title="Ethylenediamine">Ethylenediamine</a> <a href="/wiki/Ligand" title="Ligand">ligand</a> chelating to a metal with two bonds</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Cu_chelate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Cu_chelate.svg/220px-Cu_chelate.svg.png" decoding="async" width="220" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Cu_chelate.svg/330px-Cu_chelate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/38/Cu_chelate.svg/440px-Cu_chelate.svg.png 2x" data-file-width="310" data-file-height="131" /></a><figcaption>Cu<sup>2+</sup> <a href="/wiki/Coordination_complex" title="Coordination complex">complexes</a> with nonchelating <a href="/wiki/Methylamine" title="Methylamine">methylamine</a> (left) <i>and</i> chelating <a href="/wiki/Ethylenediamine" title="Ethylenediamine">ethylenediamine</a> (right) ligands</figcaption></figure> <p>The chelate effect is the greater affinity of chelating ligands for a metal ion than that of similar nonchelating (monodentate) ligands for the same metal. </p><p>The thermodynamic principles underpinning the chelate effect are illustrated by the contrasting affinities of <a href="/wiki/Copper" title="Copper">copper</a>(II) for <a href="/wiki/Ethylenediamine" title="Ethylenediamine">ethylenediamine</a> (en) vs. <a href="/wiki/Methylamine" title="Methylamine">methylamine</a>. </p> <table role="presentation" style="border-collapse:collapse; margin:0 0 0 1.6em; border:none;"><tbody><tr><td style="vertical-align:middle; border:none; padding:0;" class="nowrap">Cu<sup>2+</sup> + en ⇌ [Cu(en)]<sup>2+</sup></td> <td style="vertical-align:middle; width:99%; border:none; padding:0;"></td> <td style="vertical-align:middle; border:none; padding:0;" class="nowrap"><b>(<span id="math_1" class="reference nourlexpansion" style="font-weight:bold;">1</span>)</b></td></tr></tbody></table> <table role="presentation" style="border-collapse:collapse; margin:0 0 0 1.6em; border:none;"><tbody><tr><td style="vertical-align:middle; border:none; padding:0;" class="nowrap">Cu<sup>2+</sup> + 2 MeNH<sub>2</sub> ⇌ [Cu(MeNH<sub>2</sub>)<sub>2</sub>]<sup>2+</sup></td> <td style="vertical-align:middle; width:99%; border:none; padding:0;"></td> <td style="vertical-align:middle; border:none; padding:0;" class="nowrap"><b>(<span id="math_2" class="reference nourlexpansion" style="font-weight:bold;">2</span>)</b></td></tr></tbody></table> <p>In (<b><a href="#math_1">1</a></b>) the ethylenediamine forms a chelate complex with the copper ion. Chelation results in the formation of a five-membered CuC<sub>2</sub>N<sub>2</sub> ring. In (<b><a href="#math_2">2</a></b>) the bidentate ligand is replaced by two <a href="/wiki/Denticity" title="Denticity">monodentate</a> methylamine ligands of approximately the same donor power, indicating that the Cu–N bonds are approximately the same in the two reactions. </p><p>The <a href="/wiki/Equilibrium_thermodynamics" title="Equilibrium thermodynamics">thermodynamic</a> approach to describing the chelate effect considers the <a href="/wiki/Equilibrium_constant" title="Equilibrium constant">equilibrium constant</a> for the reaction: the larger the equilibrium constant, the higher the concentration of the complex. </p> <table role="presentation" style="border-collapse:collapse; margin:0 0 0 1.6em; border:none;"><tbody><tr><td style="vertical-align:middle; border:none; padding:0;" class="nowrap">[Cu(en)] = <i>β</i><sub>11</sub>[Cu][en]</td> <td style="vertical-align:middle; width:99%; border:none; padding:0;"></td> <td style="vertical-align:middle; border:none; padding:0;" class="nowrap"><b>(<span id="math_3" class="reference nourlexpansion" style="font-weight:bold;">3</span>)</b></td></tr></tbody></table> <table role="presentation" style="border-collapse:collapse; margin:0 0 0 1.6em; border:none;"><tbody><tr><td style="vertical-align:middle; border:none; padding:0;" class="nowrap">[Cu(MeNH<sub>2</sub>)<sub>2</sub>] = <i>β</i><sub>12</sub>[Cu][MeNH<sub>2</sub>]<sup>2</sup></td> <td style="vertical-align:middle; width:99%; border:none; padding:0;"></td> <td style="vertical-align:middle; border:none; padding:0;" class="nowrap"><b>(<span id="math_4" class="reference nourlexpansion" style="font-weight:bold;">4</span>)</b></td></tr></tbody></table> <p>Electrical charges have been omitted for simplicity of notation. The square brackets indicate concentration, and the subscripts to the <a href="/wiki/Stability_constants_of_complexes" title="Stability constants of complexes">stability constants</a>, <i>β</i>, indicate the <a href="/wiki/Stoichiometry" title="Stoichiometry">stoichiometry</a> of the complex. When the <a href="/wiki/Analytical_concentration" class="mw-redirect" title="Analytical concentration">analytical concentration</a> of methylamine is twice that of ethylenediamine and the concentration of copper is the same in both reactions, the concentration [Cu(en)] is much higher than the concentration [Cu(MeNH<sub>2</sub>)<sub>2</sub>] because <span class="nowrap"><i>β</i><sub>11</sub> ≫ <i>β</i><sub>12</sub></span>. </p><p>An equilibrium constant, <i>K</i>, is related to the standard <a href="/wiki/Gibbs_energy" class="mw-redirect" title="Gibbs energy">Gibbs free energy</a>, <span class="nowrap">⁠<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^{\ominus }}"> <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^{\ominus }}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/783df781bd2cde06d7956470e952c27226a4e203" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.338ex; width:5.273ex; height:2.509ex;" alt="{\displaystyle \Delta G^{\ominus }}"></span>⁠</span> by </p> <dl><dd><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^{\ominus }=-RT\ln K=\Delta H^{\ominus }-T\Delta S^{\ominus }}"> <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> <mo>=</mo> <mo>−</mo> <mi>R</mi> <mi>T</mi> <mi>ln</mi> <mo>⁡</mo> <mi>K</mi> <mo>=</mo> <mi mathvariant="normal">Δ</mi> <msup> <mi>H</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>⊖</mo> </mrow> </msup> <mo>−</mo> <mi>T</mi> <mi mathvariant="normal">Δ</mi> <msup> <mi>S</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>⊖</mo> </mrow> </msup> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \Delta G^{\ominus }=-RT\ln K=\Delta H^{\ominus }-T\Delta S^{\ominus }}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/c0402d0b277587e6c641c563bc08245555f19248" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:36.453ex; height:2.676ex;" alt="{\displaystyle \Delta G^{\ominus }=-RT\ln K=\Delta H^{\ominus }-T\Delta S^{\ominus }}"></span></dd></dl> <p>where <i>R</i> is the <a href="/wiki/Gas_constant" title="Gas constant">gas constant</a> and <i>T</i> is the temperature in <a href="/wiki/Kelvin" title="Kelvin">kelvins</a>. <span class="nowrap">⁠<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 H^{\ominus }}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi mathvariant="normal">Δ</mi> <msup> <mi>H</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>⊖</mo> </mrow> </msup> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \Delta H^{\ominus }}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/e7ca2ac7d655e35bf2076604abc115a3fe696542" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.338ex; width:5.55ex; height:2.509ex;" alt="{\displaystyle \Delta H^{\ominus }}"></span>⁠</span> is the standard <a href="/wiki/Enthalpy" title="Enthalpy">enthalpy</a> change of the reaction and <span class="nowrap">⁠<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 S^{\ominus }}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi mathvariant="normal">Δ</mi> <msup> <mi>S</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>⊖</mo> </mrow> </msup> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \Delta S^{\ominus }}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/15ad70acf559d9cd447a469bd375f13b6424b30c" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.338ex; width:4.968ex; height:2.509ex;" alt="{\displaystyle \Delta S^{\ominus }}"></span>⁠</span> is the standard <a href="/wiki/Entropy_(statistical_thermodynamics)" title="Entropy (statistical thermodynamics)">entropy</a> change. </p><p>Since the enthalpy should be approximately the same for the two reactions, the difference between the two stability constants is due to the effects of entropy. In equation (<b><a href="#math_1">1</a></b>) there are two particles on the left and one on the right, whereas in equation (<b><a href="#math_2">2</a></b>) there are three particles on the left and one on the right. This difference means that less <a href="/wiki/Entropy_(order_and_disorder)" title="Entropy (order and disorder)">entropy of disorder</a> is lost when the chelate complex is formed with bidentate ligand than when the complex with monodentate ligands is formed. This is one of the factors contributing to the entropy difference. Other factors include solvation changes and ring formation. Some experimental data to illustrate the effect are shown in the following table.<sup id="cite_ref-GE_4-0" class="reference"><a href="#cite_note-GE-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <tbody><tr> <th>Equilibrium</th> <th>log <i>β</i></th> <th><span class="nowrap">⁠<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^{\ominus }}"> <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^{\ominus }}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/783df781bd2cde06d7956470e952c27226a4e203" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.338ex; width:5.273ex; height:2.509ex;" alt="{\displaystyle \Delta G^{\ominus }}"></span>⁠</span></th> <th><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 H^{\ominus }\mathrm {/kJ\ mol^{-1}} }"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi mathvariant="normal">Δ</mi> <msup> <mi>H</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>⊖</mo> </mrow> </msup> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>/</mo> </mrow> <mi mathvariant="normal">k</mi> <mi mathvariant="normal">J</mi> <mtext> </mtext> <mi mathvariant="normal">m</mi> <mi mathvariant="normal">o</mi> <msup> <mi mathvariant="normal">l</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> <mn>1</mn> </mrow> </msup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \Delta H^{\ominus }\mathrm {/kJ\ mol^{-1}} }</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/ead019ec44c0b7b79250c55520d2bf8624e525e8" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.838ex; width:15.794ex; height:3.176ex;" alt="{\displaystyle \Delta H^{\ominus }\mathrm {/kJ\ mol^{-1}} }"></span></th> <th><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 -T\Delta S^{\ominus }\mathrm {/kJ\ mol^{-1}} }"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mo>−</mo> <mi>T</mi> <mi mathvariant="normal">Δ</mi> <msup> <mi>S</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>⊖</mo> </mrow> </msup> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>/</mo> </mrow> <mi mathvariant="normal">k</mi> <mi mathvariant="normal">J</mi> <mtext> </mtext> <mi mathvariant="normal">m</mi> <mi mathvariant="normal">o</mi> <msup> <mi mathvariant="normal">l</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> <mn>1</mn> </mrow> </msup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle -T\Delta S^{\ominus }\mathrm {/kJ\ mol^{-1}} }</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/32c88e67253b65847cd73e5bfc24137bb2ebd68b" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.838ex; width:18.656ex; height:3.176ex;" alt="{\displaystyle -T\Delta S^{\ominus }\mathrm {/kJ\ mol^{-1}} }"></span> </th></tr> <tr> <td>Cu<sup>2+</sup> + 2 MeNH<sub>2</sub> ⇌ Cu(MeNH<sub>2</sub>)<sub>2</sub><sup>2+</sup> </td> <td>6.55</td> <td>−37.4</td> <td>−57.3</td> <td>19.9 </td></tr> <tr> <td>Cu<sup>2+</sup> + en ⇌ Cu(en)<sup>2+</sup> </td> <td>10.62</td> <td>−60.67</td> <td>−56.48</td> <td>−4.19 </td></tr></tbody></table> <p>These data confirm that the enthalpy changes are approximately equal for the two reactions and that the main reason for the greater stability of the chelate complex is the entropy term, which is much less unfavorable. In general it is difficult to account precisely for thermodynamic values in terms of changes in solution at the molecular level, but it is clear that the chelate effect is predominantly an effect of entropy. </p><p>Other explanations, including that of <a href="/wiki/Gerold_Schwarzenbach" title="Gerold Schwarzenbach">Schwarzenbach</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> are discussed in Greenwood and Earnshaw (<i>loc.cit</i>). </p> <div class="mw-heading mw-heading2"><h2 id="In_nature">In nature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=2" title="Edit section: In nature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Numerous <a href="/wiki/Biomolecules" class="mw-redirect" title="Biomolecules">biomolecules</a> exhibit the ability to dissolve certain metal <a href="/wiki/Cation" class="mw-redirect" title="Cation">cations</a>. Thus, <a href="/wiki/Protein" title="Protein">proteins</a>, <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a>, and polynucleic acids are excellent polydentate ligands for many metal ions. Organic compounds such as the amino acids <a href="/wiki/Glutamic_acid" title="Glutamic acid">glutamic acid</a> and <a href="/wiki/Histidine" title="Histidine">histidine</a>, organic diacids such as <a href="/wiki/Malate" class="mw-redirect" title="Malate">malate</a>, and polypeptides such as <a href="/wiki/Phytochelatin" title="Phytochelatin">phytochelatin</a> are also typical chelators. In addition to these adventitious chelators, several biomolecules are specifically produced to bind certain metals (see next section).<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><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><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-Lippard_9-0" class="reference"><a href="#cite_note-Lippard-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Virtually all metalloenzymes feature metals that are chelated, usually to peptides or cofactors and prosthetic groups.<sup id="cite_ref-Lippard_9-1" class="reference"><a href="#cite_note-Lippard-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Such chelating agents include the <a href="/wiki/Porphyrin" title="Porphyrin">porphyrin</a> rings in <a href="/wiki/Hemoglobin" title="Hemoglobin">hemoglobin</a> and <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a>. Many microbial species produce water-soluble pigments that serve as chelating agents, termed <a href="/wiki/Siderophores" class="mw-redirect" title="Siderophores">siderophores</a>. For example, species of <i><a href="/wiki/Pseudomonas" title="Pseudomonas">Pseudomonas</a></i> are known to secrete <a href="/w/index.php?title=Pyochelin&action=edit&redlink=1" class="new" title="Pyochelin (page does not exist)">pyochelin</a> and <a href="/wiki/Pyoverdine" title="Pyoverdine">pyoverdine</a> that bind iron. <a href="/wiki/Enterobactin" title="Enterobactin">Enterobactin</a>, produced by <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">E. coli</a></i>, is the strongest chelating agent known. The marine <a href="/wiki/Mussel" title="Mussel">mussels</a> use metal chelation, especially Fe<sup>3+</sup> chelation with the <a href="/wiki/L-DOPA" title="L-DOPA">Dopa</a> residues in mussel foot protein-1 to improve the strength of the threads that they use to secure themselves to surfaces.<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><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><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>In earth science, chemical <a href="/wiki/Weathering" title="Weathering">weathering</a> is attributed to organic chelating agents (e.g., <a href="/wiki/Peptide" title="Peptide">peptides</a> and <a href="/wiki/Sugar" title="Sugar">sugars</a>) that extract <a href="/wiki/Metal_ions" class="mw-redirect" title="Metal ions">metal ions</a> from minerals and rocks.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Most metal complexes in the environment and in nature are bound in some form of chelate ring (e.g., with a <a href="/wiki/Humic_acid" class="mw-redirect" title="Humic acid">humic acid</a> or a protein). Thus, metal chelates are relevant to the mobilization of <a href="/wiki/Metals" class="mw-redirect" title="Metals">metals</a> in the <a href="/wiki/Soil" title="Soil">soil</a>, the uptake and the accumulation of <a href="/wiki/Metals" class="mw-redirect" title="Metals">metals</a> into <a href="/wiki/Plants" class="mw-redirect" title="Plants">plants</a> and <a href="/wiki/Microorganism" title="Microorganism">microorganisms</a>. Selective chelation of <a href="/wiki/Heavy_metals" class="mw-redirect" title="Heavy metals">heavy metals</a> is relevant to <a href="/wiki/Bioremediation" title="Bioremediation">bioremediation</a> (e.g., removal of <a href="/wiki/Caesium-137" title="Caesium-137"><sup>137</sup>Cs</a> from <a href="/wiki/Radioactive_waste" title="Radioactive waste">radioactive waste</a>).<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=3" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Animal_feed_additives">Animal feed additives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=4" title="Edit section: Animal feed additives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Synthetic chelates such as <a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">ethylenediaminetetraacetic acid</a> (EDTA) proved too stable and not nutritionally viable. If the mineral was taken from the EDTA ligand, the ligand could not be used by the body and would be expelled. During the expulsion process, the EDTA ligand randomly chelated and stripped other minerals from the body.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> According to the Association of American Feed Control Officials (AAFCO), a metal–amino acid chelate is defined as the product resulting from the reaction of metal ions from a soluble metal salt with amino acids, with a <a href="/wiki/Mole_ratio" class="mw-redirect" title="Mole ratio">mole ratio</a> in the range of 1–3 (preferably 2) moles of amino acids for one mole of metal.<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. (October 2018)">citation needed</span></a></i>]</sup> The average weight of the hydrolyzed amino acids must be approximately 150 and the resulting molecular weight of the chelate must not exceed 800 <a href="/wiki/Dalton_(unit)" title="Dalton (unit)">Da</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. (December 2015)">citation needed</span></a></i>]</sup> Since the early development of these compounds, much more research has been conducted, and has been applied to human nutrition products in a similar manner to the animal nutrition experiments that pioneered the technology. <a href="/wiki/Iron_supplement" title="Iron supplement">Ferrous bis-glycinate</a> is an example of one of these compounds that has been developed for human nutrition.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Dental_use">Dental use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=5" title="Edit section: Dental use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Dentin" title="Dentin">Dentin</a> adhesives were first designed and produced in the 1950s based on a co-monomer chelate with calcium on the surface of the tooth and generated very weak water-resistant chemical bonding (2–3 MPa).<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Chelation_therapy">Chelation therapy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=6" title="Edit section: Chelation therapy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Chelation_therapy" title="Chelation therapy">Chelation therapy</a> is an antidote for poisoning by <a href="/wiki/Mercury_poisoning" title="Mercury poisoning">mercury</a>, <a href="/wiki/Arsenic" title="Arsenic">arsenic</a>, and <a href="/wiki/Lead" title="Lead">lead</a>. Chelating agents convert these metal ions into a chemically and biochemically inert form that can be excreted. Chelation using <a href="/wiki/Calcium_disodium_EDTA" class="mw-redirect" title="Calcium disodium EDTA">calcium disodium EDTA</a> has been approved by the <a href="/wiki/U.S._Food_and_Drug_Administration" class="mw-redirect" title="U.S. Food and Drug Administration">U.S. Food and Drug Administration</a> (FDA) for serious cases of <a href="/wiki/Lead_poisoning" title="Lead poisoning">lead poisoning</a>. It is not approved for treating "<a href="/wiki/Heavy_metal_toxicity" class="mw-redirect" title="Heavy metal toxicity">heavy metal toxicity</a>".<sup id="cite_ref-warning_18-0" class="reference"><a href="#cite_note-warning-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Although beneficial in cases of serious lead poisoning, use of disodium EDTA (edetate disodium) instead of calcium disodium EDTA has resulted in fatalities due to <a href="/wiki/Hypocalcemia" title="Hypocalcemia">hypocalcemia</a>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Disodium EDTA is not approved by the FDA for any use,<sup id="cite_ref-warning_18-1" class="reference"><a href="#cite_note-warning-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> and all FDA-approved chelation therapy products require a prescription.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Contrast_agents">Contrast agents</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=7" title="Edit section: Contrast agents"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chelate complexes of <a href="/wiki/Gadolinium" title="Gadolinium">gadolinium</a> are often used as <a href="/wiki/Contrast_medium" class="mw-redirect" title="Contrast medium">contrast agents</a> in <a href="/wiki/MRI" class="mw-redirect" title="MRI">MRI scans</a>, although <a href="/wiki/Iron" title="Iron">iron</a> particle and <a href="/wiki/Manganese" title="Manganese">manganese</a> chelate complexes have also been explored.<sup id="cite_ref-:0_21-0" class="reference"><a href="#cite_note-:0-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Bifunctional chelate complexes of <a href="/wiki/Zirconium" title="Zirconium">zirconium</a>, <a href="/wiki/Gallium" title="Gallium">gallium</a>, <a href="/wiki/Fluorine" title="Fluorine">fluorine</a>, <a href="/wiki/Copper" title="Copper">copper</a>, <a href="/wiki/Yttrium" title="Yttrium">yttrium</a>, <a href="/wiki/Bromine" title="Bromine">bromine</a>, or <a href="/wiki/Iodine" title="Iodine">iodine</a> are often used for conjugation to <a href="/wiki/Monoclonal_antibodies" class="mw-redirect" title="Monoclonal antibodies">monoclonal antibodies</a> for use in antibody-based <a href="/wiki/PET_imaging" class="mw-redirect" title="PET imaging">PET imaging</a>.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> These chelate complexes often employ the usage of <a href="/wiki/Hexadentate_ligand" title="Hexadentate ligand">hexadentate ligands</a> such as <a href="/w/index.php?title=Desferrioxamine_B&action=edit&redlink=1" class="new" title="Desferrioxamine B (page does not exist)">desferrioxamine B</a> (DFO), according to Meijs <i>et al.</i>,<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> and the gadolinium complexes often employ the usage of octadentate ligands such as DTPA, according to Desreux <i>et al</i>.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Auranofin" title="Auranofin">Auranofin</a>, a chelate complex of <a href="/wiki/Gold" title="Gold">gold</a>, is used in the treatment of rheumatoid arthritis, and <a href="/wiki/Penicillamine" title="Penicillamine">penicillamine</a>, which forms chelate complexes of <a href="/wiki/Copper" title="Copper">copper</a>, is used in the treatment of <a href="/wiki/Wilson%27s_disease" title="Wilson's disease">Wilson's disease</a> and <a href="/wiki/Cystinuria" title="Cystinuria">cystinuria</a>, as well as refractory rheumatoid arthritis.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Nutritional_advantages_and_issues">Nutritional advantages and issues</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=8" title="Edit section: Nutritional advantages and issues"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chelation in the intestinal tract is a cause of numerous interactions between drugs and metal ions (also known as "<a href="/wiki/Dietary_mineral" class="mw-redirect" title="Dietary mineral">minerals</a>" in nutrition). As examples, <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> <a href="/wiki/Medication" title="Medication">drugs</a> of the <a href="/wiki/Tetracycline" title="Tetracycline">tetracycline</a> and <a href="/wiki/Quinolone_antibiotic" title="Quinolone antibiotic">quinolone</a> families are chelators of <a href="/wiki/Iron" title="Iron">Fe</a><sup>2+</sup>, <a href="/wiki/Calcium" title="Calcium">Ca</a><sup>2+</sup>, and <a href="/wiki/Magnesium" title="Magnesium">Mg</a><sup>2+</sup> ions.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>EDTA, which binds to calcium, is used to alleviate the <a href="/wiki/Hypercalcemia" class="mw-redirect" title="Hypercalcemia">hypercalcemia</a> that often results from <a href="/wiki/Band_keratopathy" title="Band keratopathy">band keratopathy</a>. The calcium may then be removed from the <a href="/wiki/Cornea" title="Cornea">cornea</a>, allowing for some increase in clarity of vision for the patient.<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. (May 2021)">citation needed</span></a></i>]</sup> </p><p><a href="/wiki/Homogeneous_catalyst" class="mw-redirect" title="Homogeneous catalyst">Homogeneous catalysts</a> are often chelated complexes. A representative example is the use of <a href="/wiki/BINAP" title="BINAP">BINAP</a> (a bidentate <a href="/wiki/Phosphine" title="Phosphine">phosphine</a>) in <a href="/wiki/Noyori_asymmetric_hydrogenation" class="mw-redirect" title="Noyori asymmetric hydrogenation">Noyori asymmetric hydrogenation</a> and asymmetric isomerization. The latter has the practical use of manufacture of synthetic <a href="/wiki/Menthol" title="Menthol">(–)-menthol</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Cleaning_and_water_softening">Cleaning and water softening</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=9" title="Edit section: Cleaning and water softening"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A chelating agent is the main component of some rust removal formulations. <a href="/wiki/Citric_acid#Cleaning_and_chelating_agent" title="Citric acid">Citric acid</a> is used to <a href="/wiki/Water_softening" title="Water softening">soften water</a> in <a href="/wiki/Soap" title="Soap">soaps</a> and laundry <a href="/wiki/Detergent" title="Detergent">detergents</a>. A common synthetic chelator is <a href="/wiki/EDTA" class="mw-redirect" title="EDTA">EDTA</a>. <a href="/wiki/Phosphonate" title="Phosphonate">Phosphonates</a> are also well-known chelating agents. Chelators are used in water treatment programs and specifically in <a href="/w/index.php?title=Steam_engineering&action=edit&redlink=1" class="new" title="Steam engineering (page does not exist)">steam engineering</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 2023)">citation needed</span></a></i>]</sup> Although the treatment is often referred to as "softening", chelation has little effect on the water's mineral content, other than to make it soluble and lower the water's <a href="/wiki/PH" title="PH">pH</a> level. </p> <div class="mw-heading mw-heading3"><h3 id="Fertilizers">Fertilizers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=10" title="Edit section: Fertilizers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metal chelate compounds are common components of fertilizers to provide micronutrients. These micronutrients (manganese, iron, zinc, copper) are required for the health of the plants. Most fertilizers contain phosphate salts that, in the absence of chelating agents, typically convert these metal ions into insoluble solids that are of no nutritional value to the plants. <a href="/wiki/EDTA" class="mw-redirect" title="EDTA">EDTA</a> is the typical chelating agent that keeps these metal ions in a soluble form.<sup id="cite_ref-Ullmann_30-0" class="reference"><a href="#cite_note-Ullmann-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Economic_situation">Economic situation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=11" title="Edit section: Economic situation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because of their wide needs, the overall chelating agents growth was 4% annually during 2009–2014<sup id="cite_ref-:1_31-0" class="reference"><a href="#cite_note-:1-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> and the trend is likely to increase. <a href="/wiki/Aminopolycarboxylic_acid" title="Aminopolycarboxylic acid">Aminopolycarboxylic acids</a> chelators are the most widely consumed chelating agents; however, the percentage of the greener alternative chelators in this category continues to grow.<sup id="cite_ref-:2_32-0" class="reference"><a href="#cite_note-:2-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> The consumption of traditional aminopolycarboxylates chelators, in particular the EDTA (<a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">ethylenediaminetetraacetic acid</a>) and NTA (<a href="/wiki/Nitrilotriacetic_acid" title="Nitrilotriacetic acid">nitrilotriacetic acid</a>), is declining (−6% annually), because of the persisting concerns over their toxicity and negative environmental impact.<sup id="cite_ref-:1_31-1" class="reference"><a href="#cite_note-:1-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> In 2013, these greener alternative chelants represented approximately 15% of the total aminopolycarboxylic acids demand. This is expected to rise to around 21% by 2018, replacing and aminophosphonic acids used in cleaning applications.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:2_32-1" class="reference"><a href="#cite_note-:2-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_31-2" class="reference"><a href="#cite_note-:1-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Examples of some Greener alternative chelating agents include <a href="/wiki/Ethylenediaminedisuccinic_acid" class="mw-redirect" title="Ethylenediaminedisuccinic acid">ethylenediamine disuccinic acid</a> (EDDS), <a href="/wiki/Polyaspartic_acid" title="Polyaspartic acid">polyaspartic acid</a> (PASA), <a href="/wiki/Methylglycinediacetic_acid" class="mw-redirect" title="Methylglycinediacetic acid">methylglycinediacetic acid</a> (MGDA), <a href="/w/index.php?title=Glutamic_diacetic_acid&action=edit&redlink=1" class="new" title="Glutamic diacetic acid (page does not exist)">glutamic diacetic acid</a> (L-GLDA), <a href="/wiki/Citric_acid" title="Citric acid">citrate</a>, <a href="/wiki/Gluconic_acid" title="Gluconic acid">gluconic acid</a>, amino acids, plant extracts etc.<sup id="cite_ref-:2_32-2" class="reference"><a href="#cite_note-:2-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reversal">Reversal</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=12" title="Edit section: Reversal"><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">See also: <a href="/wiki/Transmetalation" title="Transmetalation">Transmetalation</a></div> <p>Dechelation (or de-chelation) is a reverse process of the chelation in which the chelating agent is recovered by acidifying solution with a mineral acid to form a precipitate.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page: 7">: 7 </span></sup> </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=Chelation&action=edit&section=13" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/EDDS" title="EDDS">EDDS</a> – chemical compound<span style="display:none" class="category-wikidata-fallback-annotation">Pages displaying wikidata descriptions as a fallback</span></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=Chelation&action=edit&section=14" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i><span typeof="mw:File"><a href="//creativecommons.org/licenses/by/4.0/" title="creativecommons:by/4.0/"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Creative_Commons_by_small.svg/80px-Creative_Commons_by_small.svg.png" decoding="async" width="80" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Creative_Commons_by_small.svg/120px-Creative_Commons_by_small.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Creative_Commons_by_small.svg/160px-Creative_Commons_by_small.svg.png 2x" data-file-width="80" data-file-height="15" /></a></span> This article incorporates <a rel="nofollow" class="external text" href="https://juniperpublishers.com/omcij/pdf/OMCIJ.MS.ID.555694.pdf">text</a> by Kaana Asemave available under the <a href="//creativecommons.org/licenses/by/4.0/" class="extiw" title="creativecommons:by/4.0/">CC BY 4.0</a> license.</i> </p> <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 mw-references-columns"><ol class="references"> <li id="cite_note-IUPAC-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-IUPAC_1-0">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://goldbook.iupac.org/C01012.html">IUPAC definition of chelation.</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">Latin <i><a href="/wiki/Chela_(organ)" class="mw-redirect" title="Chela (organ)">chela</a></i>, from Greek, denotes a claw.</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"><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="CITEREFMorganDrew1920" class="citation journal cs1">Morgan GT, Drew HD (1920). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1429747">"CLXII.—Researches on residual affinity and co-ordination. 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"Ethylenediaminetetraacetic Acid and Related Chelating Agents". <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.a10_095.pub2">10.1002/14356007.a10_095.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Ethylenediaminetetraacetic+Acid+and+Related+Chelating+Agents&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.date=2011&rft_id=info%3Adoi%2F10.1002%2F14356007.a10_095.pub2&rft.isbn=978-3527306732&rft.aulast=Hart&rft.aufirst=J.+Roger&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChelation" class="Z3988"></span></span> </li> <li id="cite_note-:1-31"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_31-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_31-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:1_31-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">(2013) IHS Chemical, Chemical Insight and Forecasting: Chelating Agents.</span> </li> <li id="cite_note-:2-32"><span class="mw-cite-backlink">^ <a href="#cite_ref-:2_32-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:2_32-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:2_32-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">Dixon NJ (2012) Greener chelating agents, In Handbook of green chemistry: Designing safer chemicals. Wiley 9: 281-307.</span> </li> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text">Kołodyńska D (2011) Chelating agents of a new generation as an alternative to conventional chelators for heavy metal ions removal from different waste waters. In Expanding Issues in Desalination pp. 339-370.</span> </li> <li id="cite_note-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-34">^</a></b></span> <span class="reference-text">Kolodynska D (2013) Application of a new generation of complexing agents inremoval of heavy metal ions from different wastes. Env Sci Pollut Res 20: 5939-5949.</span> </li> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRyczkowski2019" class="citation journal cs1">Ryczkowski, Janusz (2019). <a rel="nofollow" class="external text" href="https://journals.umcs.pl/aa/article/view/9864/0">"EDTA – synthesis and selected applications"</a>. <i>Annales Universitatis Mariae Curie-Sklodowska</i>. <b>74</b>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2083-358X">2083-358X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+Universitatis+Mariae+Curie-Sklodowska&rft.atitle=EDTA+%E2%80%93+synthesis+and+selected+applications&rft.volume=74&rft.date=2019&rft.issn=2083-358X&rft.aulast=Ryczkowski&rft.aufirst=Janusz&rft_id=https%3A%2F%2Fjournals.umcs.pl%2Faa%2Farticle%2Fview%2F9864%2F0&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChelation" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chelation&action=edit&section=15" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Wiktionary-logo-en-v2.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/16px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/24px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/32px-Wiktionary-logo-en-v2.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> The dictionary definition of <a href="https://en.wiktionary.org/wiki/chelate" class="extiw" title="wiktionary:chelate"><i>chelate</i></a> at Wiktionary</li></ul> <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 .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output 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href="/wiki/Template:Chemical_equilibria" title="Template:Chemical equilibria"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemical_equilibria" title="Template talk:Chemical equilibria"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemical_equilibria" title="Special:EditPage/Template:Chemical equilibria"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Chemical_equilibria" style="font-size:114%;margin:0 4em"><a href="/wiki/Chemical_equilibrium" title="Chemical equilibrium">Chemical equilibria</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Concepts</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/Chemical_stability" title="Chemical stability">Chemical stability</a></li> <li><a class="mw-selflink selflink">Chelation</a></li> <li><a href="/wiki/Dynamic_equilibrium" title="Dynamic equilibrium">Dynamic equilibrium</a></li> <li><a href="/wiki/Equilibrium_chemistry" title="Equilibrium chemistry">Equilibrium chemistry</a></li> <li><a href="/wiki/Equilibrium_stage" class="mw-redirect" title="Equilibrium stage">Equilibrium stage</a></li> <li><a href="/wiki/Thermodynamic_free_energy" title="Thermodynamic free energy">Free energy</a> <ul><li><a href="/wiki/Gibbs_free_energy" title="Gibbs free energy">Gibbs</a></li> <li><a href="/wiki/Helmholtz_free_energy" title="Helmholtz free energy">Helmholtz</a></li></ul></li> <li><a href="/wiki/Le_Chatelier%27s_principle" title="Le Chatelier's principle">Le Chatelier's principle</a></li> <li><a href="/wiki/Phase_separation" title="Phase separation">Phase separation</a></li> <li><a href="/wiki/Reversible_reaction" title="Reversible reaction">Reversible reaction</a></li> <li><a href="/wiki/Thermodynamic_equilibrium" title="Thermodynamic equilibrium">Thermodynamic equilibrium</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mathematical_model" title="Mathematical model">Models</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/Equilibrium_constant" title="Equilibrium constant">Equilibrium constant</a> <ul><li><a href="/wiki/Determination_of_equilibrium_constants" title="Determination of equilibrium constants">determination</a></li></ul></li> <li><a href="/wiki/Phase_diagram" title="Phase diagram">Phase diagram</a></li> <li><a href="/wiki/Predominance_diagram" title="Predominance diagram">Predominance diagram</a></li> <li><a href="/wiki/Phase_rule" title="Phase rule">Phase rule</a></li> <li><a href="/wiki/Reaction_quotient" title="Reaction quotient">Reaction quotient</a></li> <li><a href="/wiki/Thermodynamic_activity" title="Thermodynamic activity">Thermodynamic activity</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Applications</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/Buffer_solution" title="Buffer solution">Buffer solution</a></li> <li><a href="/wiki/Equilibrium_unfolding" title="Equilibrium unfolding">Equilibrium unfolding</a></li> <li><a href="/wiki/Liquid%E2%80%93liquid_extraction" title="Liquid–liquid extraction">Liquid–liquid extraction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Specific equilibria</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/Acid_dissociation_constant" title="Acid dissociation constant">Acid dissociation</a> <ul><li><a href="/wiki/Hammett_acidity_function" title="Hammett acidity function">Hammett acidity function</a></li></ul></li> <li><a href="/wiki/Binding_constant" title="Binding constant">Binding constant</a></li> <li><a href="/wiki/Binding_selectivity" title="Binding selectivity">Binding selectivity</a></li> <li><a href="/wiki/Stability_constants_of_complexes" title="Stability constants of complexes">Coordination complexes</a> <ul><li><a href="/wiki/Macrocyclic_effect" class="mw-redirect" title="Macrocyclic effect">Macrocyclic effect</a></li></ul></li> <li><a href="/wiki/Dissociation_constant" title="Dissociation constant">Dissociation constant</a></li> <li><a href="/wiki/Hydrolysis_constant" title="Hydrolysis constant">Hydrolysis</a></li> <li><a href="/wiki/Molecular_autoionization" title="Molecular autoionization">Self-ionization</a> <ul><li><a href="/wiki/Self-ionization_of_water" title="Self-ionization of water">of water</a></li></ul></li> <li><a href="/wiki/Partition_equilibrium" title="Partition equilibrium">Partition</a> <ul><li><a href="/wiki/Partition_coefficient" title="Partition coefficient">Distribution coefficient</a></li></ul></li> <li><a href="/wiki/Solubility_equilibrium" title="Solubility equilibrium">Solubility</a> <ul><li><a href="/wiki/Common-ion_effect" title="Common-ion effect">Common-ion effect</a></li></ul></li> <li><a href="/wiki/Vapor%E2%80%93liquid_equilibrium" title="Vapor–liquid equilibrium">Vapor–liquid</a> <ul><li><a href="/wiki/Henry%27s_law" title="Henry's law">Henry's law</a></li></ul></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Chelating_agents_/_chelation_therapy_(V03AC,_others)" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Chelating_agents" title="Template:Chelating agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chelating_agents" title="Template talk:Chelating agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chelating_agents" title="Special:EditPage/Template:Chelating agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Chelating_agents_/_chelation_therapy_(V03AC,_others)" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Chelating agents</a> / <a href="/wiki/Chelation_therapy" title="Chelation therapy">chelation therapy</a> (<a href="/wiki/ATC_code_V03#V03AC" title="ATC code V03">V03AC</a>, others)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Copper" title="Copper">Copper</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/Penicillamine" title="Penicillamine">Penicillamine</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Iron" title="Iron">Iron</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/Deferasirox" title="Deferasirox">Deferasirox</a></li> <li><a href="/wiki/Deferiprone" title="Deferiprone">Deferiprone</a></li> <li><a href="/wiki/Deferoxamine" title="Deferoxamine">Deferoxamine</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lead" title="Lead">Lead</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/Dimercaprol" title="Dimercaprol">BAL</a><sup>#</sup></li> <li><a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">EDTA</a><sup>#</sup> <ul><li><a href="/wiki/Dexrazoxane" title="Dexrazoxane">Dexrazoxane</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thallium" title="Thallium">Thallium</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/Prussian_blue" title="Prussian blue">Prussian blue</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</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/Lipoic_acid" title="Lipoic acid">ALA</a></li> <li><a href="/wiki/BAPTA" title="BAPTA">BAPTA</a></li> <li><a href="/wiki/2,3-Dimercapto-1-propanesulfonic_acid" title="2,3-Dimercapto-1-propanesulfonic acid">DMPS</a></li> <li><a href="/wiki/Dimercaptosuccinic_acid" class="mw-redirect" title="Dimercaptosuccinic acid">DMSA</a><sup>#</sup></li> <li><a href="/wiki/Pentetic_acid" title="Pentetic acid">DTPA</a></li> <li><a href="/wiki/EGTA_(chemical)" class="mw-redirect" title="EGTA (chemical)">EGTA</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></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=Chelation&oldid=1258430542">https://en.wikipedia.org/w/index.php?title=Chelation&oldid=1258430542</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">Categories</a>: <ul><li><a href="/wiki/Category:Chelating_agents" title="Category:Chelating 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