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Acid - Wikipedia

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<ul id="toc-Definitions_and_concepts-sublist" class="vector-toc-list"> <li id="toc-Arrhenius_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Arrhenius_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Arrhenius acids</span> </div> </a> <ul id="toc-Arrhenius_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brønsted–Lowry_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brønsted–Lowry_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Brønsted–Lowry acids</span> </div> </a> <ul id="toc-Brønsted–Lowry_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Lewis_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Lewis_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Lewis acids</span> </div> </a> <ul id="toc-Lewis_acids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Dissociation_and_equilibrium" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Dissociation_and_equilibrium"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Dissociation and equilibrium</span> </div> </a> <ul id="toc-Dissociation_and_equilibrium-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nomenclature" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Nomenclature</span> </div> </a> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acid_strength" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Acid_strength"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Acid strength</span> </div> </a> <ul id="toc-Acid_strength-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Lewis_acid_strength_in_non-aqueous_solutions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Lewis_acid_strength_in_non-aqueous_solutions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Lewis acid strength in non-aqueous solutions</span> </div> </a> <ul id="toc-Lewis_acid_strength_in_non-aqueous_solutions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemical_characteristics" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemical_characteristics"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Chemical characteristics</span> </div> </a> <button aria-controls="toc-Chemical_characteristics-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 Chemical characteristics subsection</span> </button> <ul id="toc-Chemical_characteristics-sublist" class="vector-toc-list"> <li id="toc-Monoprotic_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Monoprotic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Monoprotic acids</span> </div> </a> <ul id="toc-Monoprotic_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Polyprotic_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polyprotic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Polyprotic acids</span> </div> </a> <ul id="toc-Polyprotic_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Neutralization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Neutralization"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Neutralization</span> </div> </a> <ul id="toc-Neutralization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Weak_acid–weak_base_equilibrium" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Weak_acid–weak_base_equilibrium"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Weak acid–weak base equilibrium</span> </div> </a> <ul id="toc-Weak_acid–weak_base_equilibrium-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Titration" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Titration"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Titration</span> </div> </a> <button aria-controls="toc-Titration-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 Titration subsection</span> </button> <ul id="toc-Titration-sublist" class="vector-toc-list"> <li id="toc-Example:_Diprotic_acid" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Example:_Diprotic_acid"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Example: Diprotic acid</span> </div> </a> <ul id="toc-Example:_Diprotic_acid-sublist" class="vector-toc-list"> <li id="toc-Equivalence_points" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Equivalence_points"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1.1</span> <span>Equivalence points</span> </div> </a> <ul id="toc-Equivalence_points-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Buffer_regions_and_midpoints" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Buffer_regions_and_midpoints"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1.2</span> <span>Buffer regions and midpoints</span> </div> </a> <ul id="toc-Buffer_regions_and_midpoints-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Applications_of_acids" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Applications_of_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Applications of acids</span> </div> </a> <button aria-controls="toc-Applications_of_acids-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 of acids subsection</span> </button> <ul id="toc-Applications_of_acids-sublist" class="vector-toc-list"> <li id="toc-In_industry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_industry"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>In industry</span> </div> </a> <ul id="toc-In_industry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_food" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_food"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2</span> <span>In food</span> </div> </a> <ul id="toc-In_food-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_human_bodies" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_human_bodies"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.3</span> <span>In human bodies</span> </div> </a> <ul id="toc-In_human_bodies-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acid_catalysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acid_catalysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.4</span> <span>Acid catalysis</span> </div> </a> <ul id="toc-Acid_catalysis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biological_occurrence" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biological_occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Biological occurrence</span> </div> </a> <ul id="toc-Biological_occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Common_acids" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Common_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Common acids</span> </div> </a> <button aria-controls="toc-Common_acids-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 Common acids subsection</span> </button> <ul id="toc-Common_acids-sublist" class="vector-toc-list"> <li id="toc-Mineral_acids_(inorganic_acids)" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mineral_acids_(inorganic_acids)"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.1</span> <span>Mineral acids (inorganic acids)</span> </div> </a> <ul id="toc-Mineral_acids_(inorganic_acids)-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sulfonic_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sulfonic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.2</span> <span>Sulfonic acids</span> </div> </a> <ul id="toc-Sulfonic_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carboxylic_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carboxylic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.3</span> <span>Carboxylic acids</span> </div> </a> <ul id="toc-Carboxylic_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Halogenated_carboxylic_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Halogenated_carboxylic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.4</span> <span>Halogenated carboxylic acids</span> </div> </a> <ul id="toc-Halogenated_carboxylic_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Vinylogous_carboxylic_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vinylogous_carboxylic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.5</span> <span>Vinylogous carboxylic acids</span> </div> </a> <ul id="toc-Vinylogous_carboxylic_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nucleic_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nucleic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.6</span> <span>Nucleic acids</span> </div> </a> <ul id="toc-Nucleic_acids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</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"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</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" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Acid</span></h1> <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 146 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-146" 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">146 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ace mw-list-item"><a href="https://ace.wikipedia.org/wiki/Asam" title="Asam – Acehnese" lang="ace" hreflang="ace" data-title="Asam" data-language-autonym="Acèh" data-language-local-name="Acehnese" class="interlanguage-link-target"><span>Acèh</span></a></li><li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Suur" title="Suur – Afrikaans" lang="af" hreflang="af" data-title="Suur" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-als mw-list-item"><a href="https://als.wikipedia.org/wiki/S%C3%A4uren" title="Säuren – Alemannic" lang="gsw" hreflang="gsw" data-title="Säuren" data-language-autonym="Alemannisch" data-language-local-name="Alemannic" class="interlanguage-link-target"><span>Alemannisch</span></a></li><li class="interlanguage-link interwiki-anp mw-list-item"><a href="https://anp.wikipedia.org/wiki/%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="अम्ल – Angika" lang="anp" hreflang="anp" data-title="अम्ल" data-language-autonym="अंगिका" data-language-local-name="Angika" class="interlanguage-link-target"><span>अंगिका</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AD%D9%85%D8%B6" title="حمض – Arabic" lang="ar" hreflang="ar" data-title="حمض" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-an mw-list-item"><a href="https://an.wikipedia.org/wiki/Acido" title="Acido – Aragonese" lang="an" hreflang="an" data-title="Acido" data-language-autonym="Aragonés" data-language-local-name="Aragonese" class="interlanguage-link-target"><span>Aragonés</span></a></li><li class="interlanguage-link interwiki-as mw-list-item"><a href="https://as.wikipedia.org/wiki/%E0%A6%85%E0%A6%AE%E0%A7%8D%E0%A6%B2" title="অম্ল – Assamese" lang="as" hreflang="as" data-title="অম্ল" data-language-autonym="অসমীয়া" data-language-local-name="Assamese" class="interlanguage-link-target"><span>অসমীয়া</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/%C3%81cidu" title="Ácidu – Asturian" lang="ast" hreflang="ast" data-title="Ácidu" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Tur%C5%9Fu" title="Turşu – Azerbaijani" lang="az" hreflang="az" data-title="Turşu" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A2%D8%B3%DB%8C%D8%AF" title="آسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="آسید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%85%E0%A6%AE%E0%A7%8D%E0%A6%B2" title="অম্ল – Bangla" lang="bn" hreflang="bn" data-title="অম্ল" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Sng" title="Sng – Minnan" lang="nan" hreflang="nan" data-title="Sng" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-ba mw-list-item"><a href="https://ba.wikipedia.org/wiki/%D0%9A%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0%D0%BB%D0%B0%D1%80" title="Кислоталар – Bashkir" lang="ba" hreflang="ba" data-title="Кислоталар" data-language-autonym="Башҡортса" data-language-local-name="Bashkir" class="interlanguage-link-target"><span>Башҡортса</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9A%D1%96%D1%81%D0%BB%D0%BE%D1%82%D1%8B" title="Кіслоты – Belarusian" lang="be" hreflang="be" data-title="Кіслоты" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%9A%D1%96%D1%81%D1%8C%D0%BB%D1%8F" title="Кісьля – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Кісьля" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bh mw-list-item"><a href="https://bh.wikipedia.org/wiki/%E0%A4%8F%E0%A4%B8%E0%A4%BF%E0%A4%A1" title="एसिड – Bhojpuri" lang="bh" hreflang="bh" data-title="एसिड" data-language-autonym="भोजपुरी" data-language-local-name="Bhojpuri" class="interlanguage-link-target"><span>भोजपुरी</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Asido" title="Asido – Central Bikol" lang="bcl" hreflang="bcl" data-title="Asido" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9A%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bo mw-list-item"><a href="https://bo.wikipedia.org/wiki/%E0%BD%A6%E0%BE%90%E0%BE%B1%E0%BD%B4%E0%BD%A2%E0%BC%8B%E0%BD%A2%E0%BE%AB%E0%BD%A6%E0%BC%8D" title="སྐྱུར་རྫས། – Tibetan" lang="bo" hreflang="bo" data-title="སྐྱུར་རྫས།" data-language-autonym="བོད་ཡིག" data-language-local-name="Tibetan" class="interlanguage-link-target"><span>བོད་ཡིག</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Kiseline" title="Kiseline – Bosnian" lang="bs" hreflang="bs" data-title="Kiseline" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-br mw-list-item"><a href="https://br.wikipedia.org/wiki/Trenkenn" title="Trenkenn – Breton" lang="br" hreflang="br" data-title="Trenkenn" data-language-autonym="Brezhoneg" data-language-local-name="Breton" class="interlanguage-link-target"><span>Brezhoneg</span></a></li><li class="interlanguage-link interwiki-bxr mw-list-item"><a href="https://bxr.wikipedia.org/wiki/%D0%A5%D2%AF%D1%88%D1%8D%D0%BB" title="Хүшэл – Russia Buriat" lang="bxr" hreflang="bxr" data-title="Хүшэл" data-language-autonym="Буряад" data-language-local-name="Russia Buriat" class="interlanguage-link-target"><span>Буряад</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid" title="Àcid – Catalan" lang="ca" hreflang="ca" data-title="Àcid" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kyseliny" title="Kyseliny – Czech" lang="cs" hreflang="cs" data-title="Kyseliny" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-sn mw-list-item"><a href="https://sn.wikipedia.org/wiki/Nyong%27o" title="Nyong&#039;o – Shona" lang="sn" hreflang="sn" data-title="Nyong&#039;o" data-language-autonym="ChiShona" data-language-local-name="Shona" class="interlanguage-link-target"><span>ChiShona</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Asid" title="Asid – Welsh" lang="cy" hreflang="cy" data-title="Asid" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Syre" title="Syre – Danish" lang="da" hreflang="da" data-title="Syre" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-ary mw-list-item"><a href="https://ary.wikipedia.org/wiki/%D8%A3%D8%B3%D9%8A%D8%AF" title="أسيد – Moroccan Arabic" lang="ary" hreflang="ary" data-title="أسيد" data-language-autonym="الدارجة" data-language-local-name="Moroccan Arabic" class="interlanguage-link-target"><span>الدارجة</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/S%C3%A4uren" title="Säuren – German" lang="de" hreflang="de" data-title="Säuren" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Hape" title="Hape – Estonian" lang="et" hreflang="et" data-title="Hape" 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%9F%CE%BE%CF%8D" title="Οξύ – Greek" lang="el" hreflang="el" data-title="Οξύ" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-eml mw-list-item"><a href="https://eml.wikipedia.org/wiki/%C3%82zid" title="Âzid – Emiliano-Romagnolo" lang="egl" hreflang="egl" data-title="Âzid" data-language-autonym="Emiliàn e rumagnòl" data-language-local-name="Emiliano-Romagnolo" class="interlanguage-link-target"><span>Emiliàn e rumagnòl</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido" title="Ácido – Spanish" lang="es" hreflang="es" data-title="Ácido" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Acido" title="Acido – Esperanto" lang="eo" hreflang="eo" data-title="Acido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azido" title="Azido – Basque" lang="eu" hreflang="eu" data-title="Azido" 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/%D8%A7%D8%B3%DB%8C%D8%AF" title="اسید – Persian" lang="fa" hreflang="fa" data-title="اسید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-hif mw-list-item"><a href="https://hif.wikipedia.org/wiki/Tejaab" title="Tejaab – Fiji Hindi" lang="hif" hreflang="hif" data-title="Tejaab" data-language-autonym="Fiji Hindi" data-language-local-name="Fiji Hindi" class="interlanguage-link-target"><span>Fiji Hindi</span></a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/S%C3%BDra" title="Sýra – Faroese" lang="fo" hreflang="fo" data-title="Sýra" data-language-autonym="Føroyskt" data-language-local-name="Faroese" class="interlanguage-link-target"><span>Føroyskt</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Acide" title="Acide – French" lang="fr" hreflang="fr" data-title="Acide" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Aig%C3%A9ad" title="Aigéad – Irish" lang="ga" hreflang="ga" data-title="Aigéad" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gd mw-list-item"><a href="https://gd.wikipedia.org/wiki/Searbhag" title="Searbhag – Scottish Gaelic" lang="gd" hreflang="gd" data-title="Searbhag" data-language-autonym="Gàidhlig" data-language-local-name="Scottish Gaelic" class="interlanguage-link-target"><span>Gàidhlig</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/%C3%81cido" title="Ácido – Galician" lang="gl" hreflang="gl" data-title="Ácido" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-hak mw-list-item"><a href="https://hak.wikipedia.org/wiki/S%C3%B4n" title="Sôn – Hakka Chinese" lang="hak" hreflang="hak" data-title="Sôn" data-language-autonym="客家語 / Hak-kâ-ngî" data-language-local-name="Hakka Chinese" class="interlanguage-link-target"><span>客家語 / Hak-kâ-ngî</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%82%B0_(%ED%99%94%ED%95%99)" title="산 (화학) – Korean" lang="ko" hreflang="ko" data-title="산 (화학)" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ha mw-list-item"><a href="https://ha.wikipedia.org/wiki/Acid" title="Acid – Hausa" lang="ha" hreflang="ha" data-title="Acid" data-language-autonym="Hausa" data-language-local-name="Hausa" class="interlanguage-link-target"><span>Hausa</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B9%D5%A9%D5%B8%D6%82%D5%B6%D5%A5%D6%80" title="Թթուներ – Armenian" lang="hy" hreflang="hy" data-title="Թթուներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="अम्ल – Hindi" lang="hi" hreflang="hi" data-title="अम्ल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Kiseline" title="Kiseline – Croatian" lang="hr" hreflang="hr" data-title="Kiseline" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Acido" title="Acido – Ido" lang="io" hreflang="io" data-title="Acido" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-ilo mw-list-item"><a href="https://ilo.wikipedia.org/wiki/Asido" title="Asido – Iloko" lang="ilo" hreflang="ilo" data-title="Asido" data-language-autonym="Ilokano" data-language-local-name="Iloko" class="interlanguage-link-target"><span>Ilokano</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam" title="Asam – Indonesian" lang="id" hreflang="id" data-title="Asam" 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-ia mw-list-item"><a href="https://ia.wikipedia.org/wiki/Acido" title="Acido – Interlingua" lang="ia" hreflang="ia" data-title="Acido" data-language-autonym="Interlingua" data-language-local-name="Interlingua" class="interlanguage-link-target"><span>Interlingua</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/S%C3%BDra" title="Sýra – Icelandic" lang="is" hreflang="is" data-title="Sýra" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acido" title="Acido – Italian" lang="it" hreflang="it" data-title="Acido" 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%97%D7%95%D7%9E%D7%A6%D7%94" title="חומצה – Hebrew" lang="he" hreflang="he" data-title="חומצה" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Asem" title="Asem – Javanese" lang="jv" hreflang="jv" data-title="Asem" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%86%E0%B2%AE%E0%B3%8D%E0%B2%B2" title="ಆಮ್ಲ – Kannada" lang="kn" hreflang="kn" data-title="ಆಮ್ಲ" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9B%E1%83%9F%E1%83%90%E1%83%95%E1%83%90" title="მჟავა – Georgian" lang="ka" hreflang="ka" data-title="მჟავა" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-ks mw-list-item"><a href="https://ks.wikipedia.org/wiki/%D8%AA%DB%8C%D8%B2%D9%95%D8%A2%D8%A8" title="تیزٕآب – Kashmiri" lang="ks" hreflang="ks" data-title="تیزٕآب" data-language-autonym="कॉशुर / کٲشُر" data-language-local-name="Kashmiri" class="interlanguage-link-target"><span>कॉशुर / کٲشُر</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D2%9A%D1%8B%D1%88%D2%9B%D1%8B%D0%BB" title="Қышқыл – Kazakh" lang="kk" hreflang="kk" data-title="Қышқыл" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Asidi" title="Asidi – Swahili" lang="sw" hreflang="sw" data-title="Asidi" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target"><span>Kiswahili</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Asid" title="Asid – Haitian Creole" lang="ht" hreflang="ht" data-title="Asid" data-language-autonym="Kreyòl ayisyen" data-language-local-name="Haitian Creole" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-gcr mw-list-item"><a href="https://gcr.wikipedia.org/wiki/Asid" title="Asid – Guianan Creole" lang="gcr" hreflang="gcr" data-title="Asid" data-language-autonym="Kriyòl gwiyannen" data-language-local-name="Guianan Creole" class="interlanguage-link-target"><span>Kriyòl gwiyannen</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Tir%C5%9Fe" title="Tirşe – Kurdish" lang="ku" hreflang="ku" data-title="Tirşe" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9A%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Кислота – Kyrgyz" lang="ky" hreflang="ky" data-title="Кислота" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lo mw-list-item"><a href="https://lo.wikipedia.org/wiki/%E0%BA%AD%E0%BA%B2%E0%BA%8A%E0%BA%B4%E0%BA%94" title="ອາຊິດ – Lao" lang="lo" hreflang="lo" data-title="ອາຊິດ" data-language-autonym="ລາວ" data-language-local-name="Lao" class="interlanguage-link-target"><span>ລາວ</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Acidum" title="Acidum – Latin" lang="la" hreflang="la" data-title="Acidum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Sk%C4%81bes" title="Skābes – Latvian" lang="lv" hreflang="lv" data-title="Skābes" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Saier" title="Saier – Luxembourgish" lang="lb" hreflang="lb" data-title="Saier" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/R%C5%ABg%C5%A1tis" title="Rūgštis – Lithuanian" lang="lt" hreflang="lt" data-title="Rūgštis" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-li mw-list-item"><a href="https://li.wikipedia.org/wiki/Zoer" title="Zoer – Limburgish" lang="li" hreflang="li" data-title="Zoer" data-language-autonym="Limburgs" data-language-local-name="Limburgish" class="interlanguage-link-target"><span>Limburgs</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Acid" title="Acid – Lombard" lang="lmo" hreflang="lmo" data-title="Acid" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Sav" title="Sav – Hungarian" lang="hu" hreflang="hu" data-title="Sav" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9A%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Киселина – Macedonian" lang="mk" hreflang="mk" data-title="Киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-mg mw-list-item"><a href="https://mg.wikipedia.org/wiki/Asidra" title="Asidra – Malagasy" lang="mg" hreflang="mg" data-title="Asidra" data-language-autonym="Malagasy" data-language-local-name="Malagasy" class="interlanguage-link-target"><span>Malagasy</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%85%E0%B4%AE%E0%B5%8D%E0%B4%B2%E0%B4%82" title="അമ്ലം – Malayalam" lang="ml" hreflang="ml" data-title="അമ്ലം" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-mr mw-list-item"><a href="https://mr.wikipedia.org/wiki/%E0%A4%86%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="आम्ल – Marathi" lang="mr" hreflang="mr" data-title="आम्ल" data-language-autonym="मराठी" data-language-local-name="Marathi" class="interlanguage-link-target"><span>मराठी</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Asid" title="Asid – Malay" lang="ms" hreflang="ms" data-title="Asid" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mni mw-list-item"><a href="https://mni.wikipedia.org/wiki/%EA%AF%91%EA%AF%81%EA%AF%A4%EA%AF%9F_%EA%AF%83%EA%AF%8D%EA%AF%A4" title="ꯑꯁꯤꯟ ꯃꯍꯤ – Manipuri" lang="mni" hreflang="mni" data-title="ꯑꯁꯤꯟ ꯃꯍꯤ" data-language-autonym="ꯃꯤꯇꯩ ꯂꯣꯟ" data-language-local-name="Manipuri" class="interlanguage-link-target"><span>ꯃꯤꯇꯩ ꯂꯣꯟ</span></a></li><li class="interlanguage-link interwiki-cdo mw-list-item"><a href="https://cdo.wikipedia.org/wiki/S%C5%8Fng_(hu%C3%A1-h%C5%8Fk)" title="Sŏng (huá-hŏk) – Mindong" lang="cdo" hreflang="cdo" data-title="Sŏng (huá-hŏk)" data-language-autonym="閩東語 / Mìng-dĕ̤ng-ngṳ̄" data-language-local-name="Mindong" class="interlanguage-link-target"><span>閩東語 / Mìng-dĕ̤ng-ngṳ̄</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%A5%D2%AF%D1%87%D0%B8%D0%BB" title="Хүчил – Mongolian" lang="mn" hreflang="mn" data-title="Хүчил" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%A1%E1%80%80%E1%80%BA%E1%80%86%E1%80%85%E1%80%BA" title="အက်ဆစ် – Burmese" lang="my" hreflang="my" data-title="အက်ဆစ်" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Zuur_(scheikunde)" title="Zuur (scheikunde) – Dutch" lang="nl" hreflang="nl" data-title="Zuur (scheikunde)" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ne mw-list-item"><a href="https://ne.wikipedia.org/wiki/%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="अम्ल – Nepali" lang="ne" hreflang="ne" data-title="अम्ल" data-language-autonym="नेपाली" data-language-local-name="Nepali" class="interlanguage-link-target"><span>नेपाली</span></a></li><li class="interlanguage-link interwiki-new mw-list-item"><a href="https://new.wikipedia.org/wiki/%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="अम्ल – Newari" lang="new" hreflang="new" data-title="अम्ल" data-language-autonym="नेपाल भाषा" data-language-local-name="Newari" class="interlanguage-link-target"><span>नेपाल भाषा</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E9%85%B8" title="酸 – Japanese" lang="ja" hreflang="ja" data-title="酸" 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-nap mw-list-item"><a href="https://nap.wikipedia.org/wiki/%C3%81cede" title="Ácede – Neapolitan" lang="nap" hreflang="nap" data-title="Ácede" data-language-autonym="Napulitano" data-language-local-name="Neapolitan" class="interlanguage-link-target"><span>Napulitano</span></a></li><li class="interlanguage-link interwiki-ce mw-list-item"><a href="https://ce.wikipedia.org/wiki/%D0%9C%D1%83%D1%81%D1%82%D0%B0%D0%BC" title="Мустам – Chechen" lang="ce" hreflang="ce" data-title="Мустам" data-language-autonym="Нохчийн" data-language-local-name="Chechen" class="interlanguage-link-target"><span>Нохчийн</span></a></li><li class="interlanguage-link interwiki-frr mw-list-item"><a href="https://frr.wikipedia.org/wiki/S%C3%BCren" title="Süren – Northern Frisian" lang="frr" hreflang="frr" data-title="Süren" data-language-autonym="Nordfriisk" data-language-local-name="Northern Frisian" class="interlanguage-link-target"><span>Nordfriisk</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Syre" title="Syre – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Syre" 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-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Syre" title="Syre – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Syre" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-nov mw-list-item"><a href="https://nov.wikipedia.org/wiki/Aside" title="Aside – Novial" lang="nov" hreflang="nov" data-title="Aside" data-language-autonym="Novial" data-language-local-name="Novial" class="interlanguage-link-target"><span>Novial</span></a></li><li class="interlanguage-link interwiki-oc badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://oc.wikipedia.org/wiki/Acid" title="Acid – Occitan" lang="oc" hreflang="oc" data-title="Acid" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Asiidii" title="Asiidii – Oromo" lang="om" hreflang="om" data-title="Asiidii" data-language-autonym="Oromoo" data-language-local-name="Oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Kislota" title="Kislota – Uzbek" lang="uz" hreflang="uz" data-title="Kislota" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%A4%E0%A8%BF%E0%A8%9C%E0%A8%BC%E0%A8%BE%E0%A8%AC" title="ਤਿਜ਼ਾਬ – Punjabi" lang="pa" hreflang="pa" data-title="ਤਿਜ਼ਾਬ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pag mw-list-item"><a href="https://pag.wikipedia.org/wiki/Asido" title="Asido – Pangasinan" lang="pag" hreflang="pag" data-title="Asido" data-language-autonym="Pangasinan" data-language-local-name="Pangasinan" class="interlanguage-link-target"><span>Pangasinan</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%AA%DB%8C%D8%B2%D8%A7%D8%A8" title="تیزاب – Western Punjabi" lang="pnb" hreflang="pnb" data-title="تیزاب" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-jam mw-list-item"><a href="https://jam.wikipedia.org/wiki/Asid" title="Asid – Jamaican Creole English" lang="jam" hreflang="jam" data-title="Asid" data-language-autonym="Patois" data-language-local-name="Jamaican Creole English" class="interlanguage-link-target"><span>Patois</span></a></li><li class="interlanguage-link interwiki-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/S%C3%BC%C3%BCr" title="Süür – Low German" lang="nds" hreflang="nds" data-title="Süür" data-language-autonym="Plattdüütsch" data-language-local-name="Low German" class="interlanguage-link-target"><span>Plattdüütsch</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwasy" title="Kwasy – Polish" lang="pl" hreflang="pl" data-title="Kwasy" 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/%C3%81cido" title="Ácido – Portuguese" lang="pt" hreflang="pt" data-title="Ácido" 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/Acid" title="Acid – Romanian" lang="ro" hreflang="ro" data-title="Acid" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-qu mw-list-item"><a href="https://qu.wikipedia.org/wiki/P%27uchqu" title="P&#039;uchqu – Quechua" lang="qu" hreflang="qu" data-title="P&#039;uchqu" data-language-autonym="Runa Simi" data-language-local-name="Quechua" class="interlanguage-link-target"><span>Runa Simi</span></a></li><li class="interlanguage-link interwiki-rue mw-list-item"><a href="https://rue.wikipedia.org/wiki/%D0%9A%D1%8B%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Кыселина – Rusyn" lang="rue" hreflang="rue" data-title="Кыселина" data-language-autonym="Русиньскый" data-language-local-name="Rusyn" class="interlanguage-link-target"><span>Русиньскый</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9A%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D1%8B" title="Кислоты – Russian" lang="ru" hreflang="ru" data-title="Кислоты" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sah mw-list-item"><a href="https://sah.wikipedia.org/wiki/%D0%90%D2%BB%D1%8B%D1%8B%D0%B1%D0%B0" title="Аһыыба – Yakut" lang="sah" hreflang="sah" data-title="Аһыыба" data-language-autonym="Саха тыла" data-language-local-name="Yakut" class="interlanguage-link-target"><span>Саха тыла</span></a></li><li class="interlanguage-link interwiki-sa mw-list-item"><a href="https://sa.wikipedia.org/wiki/%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2%E0%A4%AE%E0%A5%8D" title="अम्लम् – Sanskrit" lang="sa" hreflang="sa" data-title="अम्लम्" data-language-autonym="संस्कृतम्" data-language-local-name="Sanskrit" class="interlanguage-link-target"><span>संस्कृतम्</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Acidi" title="Acidi – Albanian" lang="sq" hreflang="sq" data-title="Acidi" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/%C3%80citu" title="Àcitu – Sicilian" lang="scn" hreflang="scn" data-title="Àcitu" data-language-autonym="Sicilianu" data-language-local-name="Sicilian" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Acid" title="Acid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Acid" 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/Kyselina" title="Kyselina – Slovak" lang="sk" hreflang="sk" data-title="Kyselina" 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/Kislina" title="Kislina – Slovenian" lang="sl" hreflang="sl" data-title="Kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%AA%D8%B1%D8%B4" title="ترش – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ترش" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%9A%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Киселина – Serbian" lang="sr" hreflang="sr" data-title="Киселина" 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/Kiselina" title="Kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Kiselina" 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-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Asam" title="Asam – Sundanese" lang="su" hreflang="su" data-title="Asam" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Happo" title="Happo – Finnish" lang="fi" hreflang="fi" data-title="Happo" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Syra" title="Syra – Swedish" lang="sv" hreflang="sv" data-title="Syra" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Asido" title="Asido – Tagalog" lang="tl" hreflang="tl" data-title="Asido" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AE%BE%E0%AE%9F%E0%AE%BF" title="காடி – Tamil" lang="ta" hreflang="ta" data-title="காடி" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-kab mw-list-item"><a href="https://kab.wikipedia.org/wiki/Azeffar" title="Azeffar – Kabyle" lang="kab" hreflang="kab" data-title="Azeffar" data-language-autonym="Taqbaylit" data-language-local-name="Kabyle" class="interlanguage-link-target"><span>Taqbaylit</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%9A%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0%D0%BB%D0%B0%D1%80" title="Кислоталар – Tatar" lang="tt" hreflang="tt" data-title="Кислоталар" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%86%E0%B0%AE%E0%B1%8D%E0%B0%B2%E0%B0%82" title="ఆమ్లం – Telugu" lang="te" hreflang="te" data-title="ఆమ్లం" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%81%E0%B8%A3%E0%B8%94" title="กรด – Thai" lang="th" hreflang="th" data-title="กรด" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%9A%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Кислота – Tajik" lang="tg" hreflang="tg" data-title="Кислота" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Asit" title="Asit – Turkish" lang="tr" hreflang="tr" data-title="Asit" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-tyv mw-list-item"><a href="https://tyv.wikipedia.org/wiki/%D0%9A%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0%D0%BB%D0%B0%D1%80" title="Кислоталар – Tuvinian" lang="tyv" hreflang="tyv" data-title="Кислоталар" data-language-autonym="Тыва дыл" data-language-local-name="Tuvinian" class="interlanguage-link-target"><span>Тыва дыл</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B8" title="Кислоти – Ukrainian" lang="uk" hreflang="uk" data-title="Кислоти" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%AA%D8%B1%D8%B4%DB%81" title="ترشہ – Urdu" lang="ur" hreflang="ur" data-title="ترشہ" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-ug mw-list-item"><a href="https://ug.wikipedia.org/wiki/%D9%83%D9%89%D8%B3%D9%84%D8%A7%D8%AA%D8%A7" title="كىسلاتا – Uyghur" lang="ug" hreflang="ug" data-title="كىسلاتا" data-language-autonym="ئۇيغۇرچە / Uyghurche" data-language-local-name="Uyghur" class="interlanguage-link-target"><span>ئۇيغۇرچە / Uyghurche</span></a></li><li class="interlanguage-link interwiki-za mw-list-item"><a href="https://za.wikipedia.org/wiki/Soemj" title="Soemj – Zhuang" lang="za" hreflang="za" data-title="Soemj" data-language-autonym="Vahcuengh" data-language-local-name="Zhuang" class="interlanguage-link-target"><span>Vahcuengh</span></a></li><li class="interlanguage-link interwiki-vec mw-list-item"><a href="https://vec.wikipedia.org/wiki/%C3%80sido" title="Àsido – Venetian" lang="vec" hreflang="vec" data-title="Àsido" data-language-autonym="Vèneto" data-language-local-name="Venetian" class="interlanguage-link-target"><span>Vèneto</span></a></li><li class="interlanguage-link interwiki-vep mw-list-item"><a href="https://vep.wikipedia.org/wiki/Muiktuz" title="Muiktuz – Veps" lang="vep" hreflang="vep" data-title="Muiktuz" data-language-autonym="Vepsän kel’" data-language-local-name="Veps" class="interlanguage-link-target"><span>Vepsän kel’</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Acid" title="Acid – Vietnamese" lang="vi" hreflang="vi" data-title="Acid" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-fiu-vro mw-list-item"><a href="https://fiu-vro.wikipedia.org/wiki/Hapas" title="Hapas – Võro" lang="vro" hreflang="vro" data-title="Hapas" data-language-autonym="Võro" data-language-local-name="Võro" class="interlanguage-link-target"><span>Võro</span></a></li><li class="interlanguage-link interwiki-wa mw-list-item"><a href="https://wa.wikipedia.org/wiki/Seur_(tchimeye)" title="Seur (tchimeye) – Walloon" lang="wa" hreflang="wa" data-title="Seur (tchimeye)" data-language-autonym="Walon" data-language-local-name="Walloon" class="interlanguage-link-target"><span>Walon</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E9%85%B8" title="酸 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="酸" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Asido" title="Asido – Waray" lang="war" hreflang="war" data-title="Asido" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E9%85%B8" title="酸 – Wu" lang="wuu" hreflang="wuu" data-title="酸" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-yi mw-list-item"><a href="https://yi.wikipedia.org/wiki/%D7%96%D7%99%D7%99%D7%A2%D7%A8%D7%A1" title="זייערס – Yiddish" lang="yi" hreflang="yi" data-title="זייערס" data-language-autonym="ייִדיש" data-language-local-name="Yiddish" class="interlanguage-link-target"><span>ייִדיש</span></a></li><li class="interlanguage-link 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.hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about acids in chemistry. For other uses, see <a href="/wiki/Acid_(disambiguation)" class="mw-disambig" title="Acid (disambiguation)">Acid (disambiguation)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">"Acidity" and "acidic" redirect here. For the novelette, see <a href="/wiki/Acidity_(novelette)" title="Acidity (novelette)"><i>Acidity</i> (novelette)</a>. For the band, see <a href="/wiki/Acidic_(band)" title="Acidic (band)">Acidic (band)</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound giving a proton or accepting an electron pair</div> <p class="mw-empty-elt"> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Zn_reaction_with_HCl.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Zn_reaction_with_HCl.JPG/220px-Zn_reaction_with_HCl.JPG" decoding="async" width="220" height="196" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Zn_reaction_with_HCl.JPG/330px-Zn_reaction_with_HCl.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Zn_reaction_with_HCl.JPG/440px-Zn_reaction_with_HCl.JPG 2x" data-file-width="1800" data-file-height="1600" /></a><figcaption><a href="/wiki/Zinc" title="Zinc">Zinc</a>, a typical metal, reacting with <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a>, a typical acid</figcaption></figure> <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 .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · 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1em!important}.mw-parser-output .sidebar-subgroup{width:100%;margin:0;border-spacing:0}.mw-parser-output .sidebar-left{float:left;clear:left;margin:0.5em 1em 1em 0}.mw-parser-output .sidebar-none{float:none;clear:both;margin:0.5em 1em 1em 0}.mw-parser-output .sidebar-outer-title{padding:0 0.4em 0.2em;font-size:125%;line-height:1.2em;font-weight:bold}.mw-parser-output .sidebar-top-image{padding:0.4em}.mw-parser-output .sidebar-top-caption,.mw-parser-output .sidebar-pretitle-with-top-image,.mw-parser-output .sidebar-caption{padding:0.2em 0.4em 0;line-height:1.2em}.mw-parser-output .sidebar-pretitle{padding:0.4em 0.4em 0;line-height:1.2em}.mw-parser-output .sidebar-title,.mw-parser-output .sidebar-title-with-pretitle{padding:0.2em 0.8em;font-size:145%;line-height:1.2em}.mw-parser-output .sidebar-title-with-pretitle{padding:0.1em 0.4em}.mw-parser-output .sidebar-image{padding:0.2em 0.4em 0.4em}.mw-parser-output .sidebar-heading{padding:0.1em 0.4em}.mw-parser-output .sidebar-content{padding:0 0.5em 0.4em}.mw-parser-output .sidebar-content-with-subgroup{padding:0.1em 0.4em 0.2em}.mw-parser-output .sidebar-above,.mw-parser-output .sidebar-below{padding:0.3em 0.8em;font-weight:bold}.mw-parser-output .sidebar-collapse .sidebar-above,.mw-parser-output .sidebar-collapse .sidebar-below{border-top:1px solid #aaa;border-bottom:1px solid #aaa}.mw-parser-output .sidebar-navbar{text-align:right;font-size:115%;padding:0 0.4em 0.4em}.mw-parser-output .sidebar-list-title{padding:0 0.4em;text-align:left;font-weight:bold;line-height:1.6em;font-size:105%}.mw-parser-output .sidebar-list-title-c{padding:0 0.4em;text-align:center;margin:0 3.3em}@media(max-width:640px){body.mediawiki .mw-parser-output .sidebar{width:100%!important;clear:both;float:none!important;margin-left:0!important;margin-right:0!important}}body.skin--responsive .mw-parser-output .sidebar a>img{max-width:none!important}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sidebar:not(.notheme) .sidebar-list-title,html.skin-theme-clientpref-night .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle{background:transparent!important}html.skin-theme-clientpref-night .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle a{color:var(--color-progressive)!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-list-title,html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle{background:transparent!important}html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle a{color:var(--color-progressive)!important}}@media print{body.ns-0 .mw-parser-output .sidebar{display:none!important}}</style><table class="sidebar nomobile nowraplinks"><tbody><tr><th class="sidebar-title" style="background:#d3d3d3;">Acids and bases</th></tr><tr><td class="sidebar-image"><span typeof="mw:File"><a href="/wiki/File:Acetic-acid-dissociation-3D-balls.png" class="mw-file-description" title="Diagrammatic representation of the dissociation of acetic acid in aqueous solution to acetate and hydronium ions."><img alt="Diagrammatic representation of the dissociation of acetic acid in aqueous solution to acetate and hydronium ions." src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Acetic-acid-dissociation-3D-balls.png/220px-Acetic-acid-dissociation-3D-balls.png" decoding="async" width="220" height="52" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Acetic-acid-dissociation-3D-balls.png/330px-Acetic-acid-dissociation-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/Acetic-acid-dissociation-3D-balls.png/440px-Acetic-acid-dissociation-3D-balls.png 2x" data-file-width="2150" data-file-height="513" /></a></span></td></tr><tr><td class="sidebar-content hlist" style="padding:0.2em 0 0.75em;"> <ul><li><a href="/wiki/Acceptor_number" class="mw-redirect" title="Acceptor number">Acceptor number</a></li> <li><a class="mw-selflink selflink">Acid</a></li> <li><a href="/wiki/Acid%E2%80%93base_reaction" title="Acid–base reaction">Acid–base reaction</a></li> <li><a href="/wiki/Acid%E2%80%93base_homeostasis" title="Acid–base homeostasis">Acid–base homeostasis</a></li> <li><a href="/wiki/Acid_strength" title="Acid strength">Acid strength</a></li> <li><a href="/wiki/Acidity_function" title="Acidity function">Acidity function</a></li> <li><a href="/wiki/Amphoterism" title="Amphoterism">Amphoterism</a></li> <li><a href="/wiki/Base_(chemistry)" title="Base (chemistry)">Base</a></li> <li><a href="/wiki/Buffer_solution" title="Buffer solution">Buffer solutions</a></li> <li><a href="/wiki/Dissociation_constant" title="Dissociation constant">Dissociation constant</a></li> <li><a href="/wiki/Donor_number" title="Donor number">Donor number</a></li> <li><a href="/wiki/Equilibrium_chemistry" title="Equilibrium chemistry">Equilibrium chemistry</a></li> <li><a href="/wiki/Acid%E2%80%93base_extraction" title="Acid–base extraction">Extraction</a></li> <li><a href="/wiki/Hammett_acidity_function" title="Hammett acidity function">Hammett acidity function</a></li> <li><a href="/wiki/PH" title="PH">pH</a></li> <li><a href="/wiki/Proton_affinity" title="Proton affinity">Proton affinity</a></li> <li><a href="/wiki/Self-ionization_of_water" title="Self-ionization of water">Self-ionization of water</a></li> <li><a href="/wiki/Acid%E2%80%93base_titration" title="Acid–base titration">Titration</a></li> <li><a href="/wiki/Lewis_acid_catalysis" title="Lewis acid catalysis">Lewis acid catalysis</a></li> <li><a href="/wiki/Frustrated_Lewis_pair" title="Frustrated Lewis pair">Frustrated Lewis pair</a></li> <li><a href="/wiki/Chiral_Lewis_acid" title="Chiral Lewis acid">Chiral Lewis acid</a></li> <li><a href="/wiki/ECW_model" title="ECW model">ECW model</a></li></ul></td> </tr><tr><th class="sidebar-heading" style="background:#e5e5e5;"> <a class="mw-selflink selflink">Acid</a> types</th></tr><tr><td class="sidebar-content hlist" style="padding:0.2em 0 0.75em;"> <ul><li><a href="/wiki/Br%C3%B8nsted%E2%80%93Lowry_acid%E2%80%93base_theory" title="Brønsted–Lowry acid–base theory">Brønsted–Lowry</a></li> <li><a href="/wiki/Lewis_acids_and_bases" title="Lewis acids and bases">Lewis</a></li> <li><a href="/wiki/Mineral_acid" title="Mineral acid">Mineral</a></li> <li><a href="/wiki/Organic_acid" title="Organic acid">Organic</a></li> <li><a href="/wiki/Acidic_oxide" title="Acidic oxide">Oxide</a></li> <li><a href="/wiki/Strong_acid" class="mw-redirect" title="Strong acid">Strong</a></li> <li><a href="/wiki/Superacid" title="Superacid">Superacids</a></li> <li><a href="/wiki/Weak_acid" class="mw-redirect" title="Weak acid">Weak</a></li> <li><a href="/wiki/Solid_acid" title="Solid acid">Solid</a></li></ul></td> </tr><tr><th class="sidebar-heading" style="background:#e5e5e5;"> <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">Base</a> types</th></tr><tr><td class="sidebar-content hlist" style="padding:0.2em 0 0.75em;"> <ul><li><a href="/wiki/Br%C3%B8nsted%E2%80%93Lowry_acid%E2%80%93base_theory" title="Brønsted–Lowry acid–base theory">Brønsted–Lowry</a></li> <li><a href="/wiki/Lewis_acids_and_bases" title="Lewis acids and bases">Lewis</a></li> <li><a href="/wiki/Organic_base" title="Organic base">Organic</a></li> <li><a href="/wiki/Basic_oxide" title="Basic oxide">Oxide</a></li> <li><a href="/wiki/Base_(chemistry)#Strong_bases" title="Base (chemistry)">Strong</a></li> <li><a href="/wiki/Superbase" title="Superbase">Superbases</a></li> <li><a href="/wiki/Non-nucleophilic_base" title="Non-nucleophilic base">Non-nucleophilic</a></li> <li><a href="/wiki/Weak_base" title="Weak base">Weak</a></li></ul></td> </tr><tr><td class="sidebar-navbar"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Acids_and_bases" title="Template:Acids and bases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Acids_and_bases" title="Template talk:Acids and bases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Acids_and_bases" title="Special:EditPage/Template:Acids and bases"><abbr title="Edit this template">e</abbr></a></li></ul></div></td></tr></tbody></table> <p>An <b>acid</b> is a <a href="/wiki/Molecule" title="Molecule">molecule</a> or <a href="/wiki/Ion" title="Ion">ion</a> capable of either donating a <a href="/wiki/Proton" title="Proton">proton</a> (i.e. hydrogen ion, H<sup>+</sup>), known as a <a href="/wiki/Br%C3%B8nsted%E2%80%93Lowry_acid%E2%80%93base_theory" title="Brønsted–Lowry acid–base theory">Brønsted–Lowry acid</a>, or forming a <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bond</a> with an <a href="/wiki/Electron_pair" title="Electron pair">electron pair</a>, known as a <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a>.<sup id="cite_ref-IUPAC_acid_1-0" class="reference"><a href="#cite_note-IUPAC_acid-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> </p><p>The first category of acids are the proton donors, or <a href="/wiki/Br%C3%B8nsted%E2%80%93Lowry_acid%E2%80%93base_theory" title="Brønsted–Lowry acid–base theory">Brønsted–Lowry acids</a>. In the special case of <a href="/wiki/Aqueous_solution" title="Aqueous solution">aqueous solutions</a>, proton donors form the <a href="/wiki/Hydronium_ion" class="mw-redirect" title="Hydronium ion">hydronium ion</a> H<sub>3</sub>O<sup>+</sup> and are known as <a href="/wiki/Acid%E2%80%93base_reaction#Arrhenius_theory" title="Acid–base reaction">Arrhenius acids</a>. <a href="/wiki/Johannes_Nicolaus_Br%C3%B8nsted" title="Johannes Nicolaus Brønsted">Brønsted</a> and <a href="/wiki/Thomas_Martin_Lowry" class="mw-redirect" title="Thomas Martin Lowry">Lowry</a> generalized the Arrhenius theory to include non-aqueous <a href="/wiki/Solvent" title="Solvent">solvents</a>. A Brønsted or Arrhenius acid usually contains a hydrogen atom bonded to a chemical structure that is still energetically favorable after loss of H<sup>+</sup>. </p><p>Aqueous Arrhenius acids have characteristic properties that provide a practical description of an acid.<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> Acids form aqueous solutions with a sour taste, can turn blue <a href="/wiki/Litmus" title="Litmus">litmus</a> red, and react with <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">bases</a> and certain metals (like <a href="/wiki/Calcium" title="Calcium">calcium</a>) to form <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a>. The word <i>acid</i> is derived from the <a href="/wiki/Latin" title="Latin">Latin</a> <span title="Latin-language text"><i lang="la">acidus</i></span>, meaning 'sour'.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> An aqueous solution of an acid has a <a href="/wiki/PH" title="PH">pH</a> less than 7 and is colloquially also referred to as "acid" (as in "dissolved in acid"), while the strict definition refers only to the <a href="/wiki/Solute" class="mw-redirect" title="Solute">solute</a>.<sup id="cite_ref-IUPAC_acid_1-1" class="reference"><a href="#cite_note-IUPAC_acid-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> A lower pH means a higher <b>acidity</b>, and thus a higher concentration of <a href="/wiki/Hydron_(chemistry)" title="Hydron (chemistry)">positive hydrogen ions</a> in the solution. Chemicals or substances having the property of an acid are said to be <b>acidic</b>. </p><p>Common aqueous acids include <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> (a solution of <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a> that is found in <a href="/wiki/Gastric_acid" title="Gastric acid">gastric acid</a> in the stomach and activates <a href="/wiki/Digestive_enzymes" class="mw-redirect" title="Digestive enzymes">digestive enzymes</a>), <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> (vinegar is a dilute aqueous solution of this liquid), <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> (used in <a href="/wiki/Car_battery" class="mw-redirect" title="Car battery">car batteries</a>), and <a href="/wiki/Citric_acid" title="Citric acid">citric acid</a> (found in citrus fruits). As these examples show, acids (in the colloquial sense) can be solutions or pure substances, and can be derived from acids (in the strict<sup id="cite_ref-IUPAC_acid_1-2" class="reference"><a href="#cite_note-IUPAC_acid-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> sense) that are solids, liquids, or gases. <a href="/wiki/Acid_strength" title="Acid strength">Strong acids</a> and some concentrated weak acids are <a href="/wiki/Corrosive_substance" class="mw-redirect" title="Corrosive substance">corrosive</a>, but there are exceptions such as <a href="/wiki/Carborane" title="Carborane">carboranes</a> and <a href="/wiki/Boric_acid" title="Boric acid">boric acid</a>. </p><p>The second category of acids are <a href="/wiki/Lewis_acids_and_bases" title="Lewis acids and bases">Lewis acids</a>, which form a covalent bond with an electron pair. An example is <a href="/wiki/Boron_trifluoride" title="Boron trifluoride">boron trifluoride</a> (BF<sub>3</sub>), whose boron atom has a vacant <a href="/wiki/Atomic_orbital" title="Atomic orbital">orbital</a> that can form a covalent bond by sharing a lone pair of electrons on an atom in a base, for example the nitrogen atom in <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> (NH<sub>3</sub>). <a href="/wiki/Gilbert_N._Lewis" title="Gilbert N. Lewis">Lewis</a> considered this as a generalization of the Brønsted definition, so that an acid is a chemical species that accepts electron pairs either directly <i>or</i> by releasing protons (H<sup>+</sup>) into the solution, which then accept electron pairs. Hydrogen chloride, acetic acid, and most other Brønsted–Lowry acids cannot form a covalent bond with an electron pair, however, and are therefore not Lewis acids.<sup id="cite_ref-Oxtoby8th_4-0" class="reference"><a href="#cite_note-Oxtoby8th-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> Conversely, many Lewis acids are not Arrhenius or Brønsted–Lowry acids. In modern terminology, an <i>acid</i> is implicitly a Brønsted acid and not a Lewis acid, since chemists almost always refer to a Lewis acid explicitly as such.<sup id="cite_ref-Oxtoby8th_4-1" class="reference"><a href="#cite_note-Oxtoby8th-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Definitions_and_concepts">Definitions and concepts</h2></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Acid%E2%80%93base_reaction" title="Acid–base reaction">Acid–base reaction</a></div> <p>Modern definitions are concerned with the fundamental chemical reactions common to all acids. </p><p>Most acids encountered in everyday life are <a href="/wiki/Aqueous_solutions" class="mw-redirect" title="Aqueous solutions">aqueous solutions</a>, or can be dissolved in water, so the Arrhenius and Brønsted–Lowry definitions are the most relevant. </p><p>The Brønsted–Lowry definition is the most widely used definition; unless otherwise specified, acid–base reactions are assumed to involve the transfer of a proton (H<sup>+</sup>) from an acid to a base. </p><p>Hydronium ions are acids according to all three definitions. Although alcohols and amines can be Brønsted–Lowry acids, they can also function as <a href="/wiki/Lewis_base" class="mw-redirect" title="Lewis base">Lewis bases</a> due to the lone pairs of electrons on their oxygen and nitrogen atoms. </p> <div class="mw-heading mw-heading3"><h3 id="Arrhenius_acids">Arrhenius acids</h3></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Arrhenius2.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Arrhenius2.jpg/150px-Arrhenius2.jpg" decoding="async" width="150" height="188" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Arrhenius2.jpg/225px-Arrhenius2.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Arrhenius2.jpg/300px-Arrhenius2.jpg 2x" data-file-width="479" data-file-height="600" /></a><figcaption>Svante Arrhenius</figcaption></figure> <p>In 1884, <a href="/wiki/Svante_Arrhenius" title="Svante Arrhenius">Svante Arrhenius</a> attributed the properties of acidity to <a href="/wiki/Hydrogen_ion" title="Hydrogen ion">hydrogen ions</a> (H<sup>+</sup>), later described as <a href="/wiki/Proton#Hydrogen_ion" title="Proton">protons</a> or <a href="/wiki/Hydron_(chemistry)" title="Hydron (chemistry)">hydrons</a>. An <b>Arrhenius acid</b> is a substance that, when added to water, increases the concentration of H<sup>+</sup> ions in the water.<sup id="cite_ref-Oxtoby8th_4-2" class="reference"><a href="#cite_note-Oxtoby8th-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Ebbing_5-0" class="reference"><a href="#cite_note-Ebbing-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> Chemists often write H<sup>+</sup>(<i>aq</i>) and refer to the <a href="/wiki/Hydrogen_ion" title="Hydrogen ion">hydrogen ion</a> when describing acid–base reactions but the free hydrogen nucleus, a <a href="/wiki/Proton" title="Proton">proton</a>, does not exist alone in water, it exists as the <b>hydronium ion</b> (H<sub>3</sub>O<sup>+</sup>) or other forms (H<sub>5</sub>O<sub>2</sub><sup>+</sup>, H<sub>9</sub>O<sub>4</sub><sup>+</sup>). Thus, an Arrhenius acid can also be described as a substance that increases the concentration of hydronium ions when added to water. Examples include molecular substances such as hydrogen chloride and acetic acid. </p><p>An Arrhenius <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a>, on the other hand, is a substance that increases the concentration of <a href="/wiki/Hydroxide" title="Hydroxide">hydroxide</a> (OH<sup>−</sup>) ions when dissolved in water. This decreases the concentration of hydronium because the ions react to form H<sub>2</sub>O molecules: </p> <dl><dd>H<sub>3</sub>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">(aq)</sub></span></span> + OH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">(aq)</sub></span></span> ⇌ H<sub>2</sub>O<sub>(liq)</sub> + H<sub>2</sub>O<sub>(liq)</sub></dd></dl> <p>Due to this equilibrium, any increase in the concentration of hydronium is accompanied by a decrease in the concentration of hydroxide. Thus, an Arrhenius acid could also be said to be one that decreases hydroxide concentration, while an Arrhenius base increases it. </p><p>In an acidic solution, the concentration of hydronium ions is greater than 10<sup>−7</sup> <a href="/wiki/Mole_(unit)" title="Mole (unit)">moles</a> per liter. Since pH is defined as the negative logarithm of the concentration of hydronium ions, acidic solutions thus have a pH of less than 7. </p> <div class="mw-heading mw-heading3"><h3 id="Brønsted–Lowry_acids"><span id="Br.C3.B8nsted.E2.80.93Lowry_acids"></span>Brønsted–Lowry acids<span class="anchor" id="Brønsted_acids"></span></h3></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Br%C3%B8nsted%E2%80%93Lowry_acid%E2%80%93base_theory" title="Brønsted–Lowry acid–base theory">Brønsted–Lowry acid–base theory</a></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Acetic-acid-dissociation-3D-balls.png" class="mw-file-description"><img alt="Acetic acid, CH3COOH, is composed of a methyl group, CH3, bound chemically to a carboxylate group, COOH. The carboxylate group can lose a proton and donate it to a water molecule, H20, leaving behind an acetate anion CH3COO- and creating a hydronium cation H3O. This is an equilibrium reaction, so the reverse process can also take place." src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Acetic-acid-dissociation-3D-balls.png/350px-Acetic-acid-dissociation-3D-balls.png" decoding="async" width="350" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Acetic-acid-dissociation-3D-balls.png/525px-Acetic-acid-dissociation-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/Acetic-acid-dissociation-3D-balls.png/700px-Acetic-acid-dissociation-3D-balls.png 2x" data-file-width="2150" data-file-height="513" /></a><figcaption><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a>, a <a href="/wiki/Weak_acid" class="mw-redirect" title="Weak acid">weak acid</a>, donates a proton (hydrogen ion, highlighted in green) to water in an equilibrium reaction to give the <a href="/wiki/Acetate" title="Acetate">acetate</a> ion and the <a href="/wiki/Hydronium" title="Hydronium">hydronium</a> ion. Red: oxygen, black: carbon, white: hydrogen.</figcaption></figure> <p>While the Arrhenius concept is useful for describing many reactions, it is also quite limited in its scope. In 1923, chemists <a href="/wiki/Johannes_Nicolaus_Br%C3%B8nsted" title="Johannes Nicolaus Brønsted">Johannes Nicolaus Brønsted</a> and <a href="/wiki/Thomas_Martin_Lowry" class="mw-redirect" title="Thomas Martin Lowry">Thomas Martin Lowry</a> independently recognized that acid–base reactions involve the transfer of a proton. A <b>Brønsted–Lowry acid</b> (or simply Brønsted acid) is a species that donates a proton to a Brønsted–Lowry base.<sup id="cite_ref-Ebbing_5-1" class="reference"><a href="#cite_note-Ebbing-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> Brønsted–Lowry acid–base theory has several advantages over Arrhenius theory. Consider the following reactions of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> (CH<sub>3</sub>COOH), the <a href="/wiki/Organic_acid" title="Organic acid">organic acid</a> that gives vinegar its characteristic taste: </p> <dl><dd><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COOH + H<sub class="template-chem2-sub">2</sub>O ⇌ CH<sub class="template-chem2-sub">3</sub>COO<sup class="template-chem2-sup">−</sup> + H<sub class="template-chem2-sub">3</sub>O<sup class="template-chem2-sup">+</sup></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COOH + NH<sub class="template-chem2-sub">3</sub> ⇌ CH<sub class="template-chem2-sub">3</sub>COO<sup class="template-chem2-sup">−</sup> + NH<span class="template-chem2-su"><span>+</span><span>4</span></span></span></dd></dl> <p>Both theories easily describe the first reaction: CH<sub>3</sub>COOH acts as an Arrhenius acid because it acts as a source of H<sub>3</sub>O<sup>+</sup> when dissolved in water, and it acts as a Brønsted acid by donating a proton to water. In the second example CH<sub>3</sub>COOH undergoes the same transformation, in this case donating a proton to ammonia (NH<sub>3</sub>), but does not relate to the Arrhenius definition of an acid because the reaction does not produce hydronium. Nevertheless, CH<sub>3</sub>COOH is both an Arrhenius and a Brønsted–Lowry acid. </p><p>Brønsted–Lowry theory can be used to describe reactions of <a href="/wiki/Molecule" title="Molecule">molecular compounds</a> in nonaqueous solution or the gas phase. <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a> (HCl) and ammonia combine under several different conditions to form <a href="/wiki/Ammonium_chloride" title="Ammonium chloride">ammonium chloride</a>, NH<sub>4</sub>Cl. In aqueous solution HCl behaves as <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> and exists as hydronium and chloride ions. The following reactions illustrate the limitations of Arrhenius's definition: </p> <ol><li>H<sub>3</sub>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">(aq)</sub></span></span> + Cl<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">(aq)</sub></span></span> + NH<sub>3</sub> → Cl<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">(aq)</sub></span></span> + NH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span><sub>(aq)</sub> + H<sub>2</sub>O</li> <li>HCl<sub>(benzene)</sub> + NH<sub>3(benzene)</sub> → NH<sub>4</sub>Cl<sub>(s)</sub></li> <li>HCl<sub>(g)</sub> + NH<sub>3(g)</sub> → NH<sub>4</sub>Cl<sub>(s)</sub></li></ol> <p>As with the acetic acid reactions, both definitions work for the first example, where water is the solvent and hydronium ion is formed by the HCl solute. The next two reactions do not involve the formation of ions but are still proton-transfer reactions. In the second reaction hydrogen chloride and ammonia (dissolved in <a href="/wiki/Benzene" title="Benzene">benzene</a>) react to form solid ammonium chloride in a benzene solvent and in the third gaseous HCl and NH<sub>3</sub> combine to form the solid. </p> <div class="mw-heading mw-heading3"><h3 id="Lewis_acids">Lewis acids</h3></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Lewis_acids_and_bases" title="Lewis acids and bases">Lewis acids and bases</a></div> <p>A third, only marginally related concept was proposed in 1923 by <a href="/wiki/Gilbert_N._Lewis" title="Gilbert N. Lewis">Gilbert N. Lewis</a>, which includes reactions with acid–base characteristics that do not involve a proton transfer. A <b>Lewis acid</b> is a species that accepts a pair of electrons from another species; in other words, it is an electron pair acceptor.<sup id="cite_ref-Ebbing_5-2" class="reference"><a href="#cite_note-Ebbing-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> Brønsted acid–base reactions are proton transfer reactions while Lewis acid–base reactions are electron pair transfers. Many Lewis acids are not Brønsted–Lowry acids. Contrast how the following reactions are described in terms of acid–base chemistry: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:LewisAcid.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4d/LewisAcid.png/374px-LewisAcid.png" decoding="async" width="374" height="180" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4d/LewisAcid.png/561px-LewisAcid.png 1.5x, //upload.wikimedia.org/wikipedia/commons/4/4d/LewisAcid.png 2x" data-file-width="748" data-file-height="360" /></a></span></dd></dl> <p>In the first reaction a <a href="/wiki/Fluoride" title="Fluoride">fluoride ion</a>, F<sup>−</sup>, gives up an <a href="/wiki/Lone_pair" title="Lone pair">electron pair</a> to <a href="/wiki/Boron_trifluoride" title="Boron trifluoride">boron trifluoride</a> to form the product <a href="/wiki/Tetrafluoroborate" title="Tetrafluoroborate">tetrafluoroborate</a>. Fluoride "loses" a pair of <a href="/wiki/Valence_electron" title="Valence electron">valence electrons</a> because the electrons shared in the B—F bond are located in the region of space between the two atomic <a href="/wiki/Atomic_nucleus" title="Atomic nucleus">nuclei</a> and are therefore more distant from the fluoride nucleus than they are in the lone fluoride ion. BF<sub>3</sub> is a Lewis acid because it accepts the electron pair from fluoride. This reaction cannot be described in terms of Brønsted theory because there is no proton transfer. </p><p>The second reaction can be described using either theory. A proton is transferred from an unspecified Brønsted acid to ammonia, a Brønsted base; alternatively, ammonia acts as a Lewis base and transfers a lone pair of electrons to form a bond with a hydrogen ion. The species that gains the electron pair is the Lewis acid; for example, the oxygen atom in H<sub>3</sub>O<sup>+</sup> gains a pair of electrons when one of the H—O bonds is broken and the electrons shared in the bond become localized on oxygen. </p><p>Depending on the context, a Lewis acid may also be described as an <a href="/wiki/Oxidizing_agent" title="Oxidizing agent">oxidizer</a> or an <a href="/wiki/Electrophile" title="Electrophile">electrophile</a>. Organic Brønsted acids, such as acetic, citric, or oxalic acid, are not Lewis acids.<sup id="cite_ref-Oxtoby8th_4-3" class="reference"><a href="#cite_note-Oxtoby8th-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> They dissociate in water to produce a Lewis acid, H<sup>+</sup>, but at the same time, they also yield an equal amount of a Lewis base (acetate, citrate, or oxalate, respectively, for the acids mentioned). This article deals mostly with Brønsted acids rather than Lewis acids. </p> <div class="mw-heading mw-heading2"><h2 id="Dissociation_and_equilibrium">Dissociation and equilibrium</h2></div> <p>Reactions of acids are often generalized in the form <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HA ⇌ H<sup class="template-chem2-sup">+</sup> + A<sup class="template-chem2-sup">−</sup></span>, where HA represents the acid and A<sup>−</sup> is the <a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">conjugate base</a>. This reaction is referred to as <b>protolysis</b>. The protonated form (HA) of an acid is also sometimes referred to as the <b>free acid</b>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> </p><p>Acid–base conjugate pairs differ by one proton, and can be interconverted by the addition or removal of a proton (<a href="/wiki/Protonation" title="Protonation">protonation</a> and <a href="/wiki/Deprotonation" title="Deprotonation">deprotonation</a>, respectively). The acid can be the charged species and the conjugate base can be neutral in which case the generalized reaction scheme could be written as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HA<sup class="template-chem2-sup">+</sup> ⇌ H<sup class="template-chem2-sup">+</sup> + A</span>. In solution there exists an <a href="/wiki/Chemical_equilibrium" title="Chemical equilibrium">equilibrium</a> between the acid and its conjugate base. The <a href="/wiki/Equilibrium_constant" title="Equilibrium constant">equilibrium constant</a> <i>K</i> is an expression of the equilibrium concentrations of the molecules or the ions in solution. Brackets indicate concentration, such that [H<sub>2</sub>O] means <i>the concentration of H<sub>2</sub>O</i>. The <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">acid dissociation constant</a> <i>K</i><sub>a</sub> is generally used in the context of acid–base reactions. The numerical value of <i>K</i><sub>a</sub> is equal to the <a href="/wiki/Product_(mathematics)" title="Product (mathematics)">product</a> (multiplication) of the concentrations of the products divided by the concentration of the reactants, where the reactant is the acid (HA) and the products are the conjugate base and H<sup>+</sup>. </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 K_{a}={\frac {{\ce {[H+] [A^{-}]}}}{{\ce {[HA]}}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mi>a</mi> </mrow> </msub> <mo>=</mo> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> <mo stretchy="false">]</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msup> <mtext>A</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> <mo stretchy="false">]</mo> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mtext>HA</mtext> <mo stretchy="false">]</mo> </mrow> </mrow> </mfrac> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle K_{a}={\frac {{\ce {[H+] [A^{-}]}}}{{\ce {[HA]}}}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/5ad1f54a70a45ea863263baa691826f3ee6cfb58" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -2.671ex; width:16.105ex; height:6.676ex;" alt="{\displaystyle K_{a}={\frac {{\ce {[H+] [A^{-}]}}}{{\ce {[HA]}}}}}"></span></dd></dl> <p>The stronger of two acids will have a higher <i>K</i><sub>a</sub> than the weaker acid; the ratio of hydrogen ions to acid will be higher for the stronger acid as the stronger acid has a greater tendency to lose its proton. Because the range of possible values for <i>K</i><sub>a</sub> spans many orders of magnitude, a more manageable constant, p<i>K</i><sub>a</sub> is more frequently used, where p<i>K</i><sub>a</sub> = &#8722;log<sub>10</sub> <i>K</i><sub>a</sub>. Stronger acids have a smaller p<i>K</i><sub>a</sub> than weaker acids. Experimentally determined p<i>K</i><sub>a</sub> at 25&#160;°C in aqueous solution are often quoted in textbooks and reference material. </p> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2></div> <p>Arrhenius acids are named according to their <a href="/wiki/Anion" class="mw-redirect" title="Anion">anions</a>. In the classical naming system, the ionic suffix is dropped and replaced with a new suffix, according to the table following. The prefix "hydro-" is used when the acid is made up of just hydrogen and one other element. For example, HCl has <a href="/wiki/Chloride" title="Chloride">chloride</a> as its anion, so the hydro- prefix is used, and the -ide suffix makes the name take the form <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a>. </p><p><i>Classical naming system:</i> </p> <table class="wikitable"> <tbody><tr> <th>Anion prefix </th> <th>Anion suffix </th> <th>Acid prefix </th> <th>Acid suffix </th> <th>Example </th></tr> <tr> <td>per </td> <td rowspan="2">ate </td> <td>per </td> <td rowspan="2">ic acid </td> <td><a href="/wiki/Perchloric_acid" title="Perchloric acid">perchloric acid</a> (HClO<sub>4</sub>) </td></tr> <tr> <td> </td> <td> </td> <td><a href="/wiki/Chloric_acid" title="Chloric acid">chloric acid</a> (HClO<sub>3</sub>) </td></tr> <tr> <td> </td> <td>ite </td> <td> </td> <td>ous acid </td> <td><a href="/wiki/Chlorous_acid" title="Chlorous acid">chlorous acid</a> (HClO<sub>2</sub>) </td></tr> <tr> <td>hypo </td> <td>ite </td> <td>hypo </td> <td>ous acid </td> <td><a href="/wiki/Hypochlorous_acid" title="Hypochlorous acid">hypochlorous acid</a> (HClO) </td></tr> <tr> <td> </td> <td>ide </td> <td>hydro </td> <td>ic acid </td> <td><a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> (HCl) </td></tr></tbody></table> <p>In the <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> naming system, "aqueous" is simply added to the name of the ionic compound. Thus, for hydrogen chloride, as an acid solution, the IUPAC name is aqueous hydrogen chloride. </p> <div class="mw-heading mw-heading2"><h2 id="Acid_strength">Acid strength</h2></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Acid_strength" title="Acid strength">Acid strength</a></div> <p>The strength of an acid refers to its ability or tendency to lose a proton. A strong acid is one that completely dissociates in water; in other words, one <a href="/wiki/Mole_(unit)" title="Mole (unit)">mole</a> of a strong acid HA dissolves in water yielding one mole of H<sup>+</sup> and one mole of the conjugate base, A<sup>−</sup>, and none of the protonated acid HA. In contrast, a weak acid only partially dissociates and at equilibrium both the acid and the conjugate base are in solution. Examples of <a href="/wiki/Strong_acid" class="mw-redirect" title="Strong acid">strong acids</a> are <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> (HCl), <a href="/wiki/Hydroiodic_acid" title="Hydroiodic acid">hydroiodic acid</a> (HI), <a href="/wiki/Hydrobromic_acid" title="Hydrobromic acid">hydrobromic acid</a> (HBr), <a href="/wiki/Perchloric_acid" title="Perchloric acid">perchloric acid</a> (HClO<sub>4</sub>), <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a> (HNO<sub>3</sub>) and <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> (H<sub>2</sub>SO<sub>4</sub>). In water each of these essentially ionizes 100%. The stronger an acid is, the more easily it loses a proton, H<sup>+</sup>. Two key factors that contribute to the ease of deprotonation are the <a href="/wiki/Chemical_polarity" title="Chemical polarity">polarity</a> of the H—A bond and the size of atom A, which determines the strength of the H—A bond. Acid strengths are also often discussed in terms of the stability of the conjugate base. </p><p>Stronger acids have a larger <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">acid dissociation constant</a>, <i>K</i><sub>a</sub> and a lower p<i>K</i><sub>a</sub> than weaker acids. </p><p><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acids</a>, which are organic oxyacids, are a class of strong acids. A common example is <a href="/wiki/Toluenesulfonic_acid" class="mw-redirect" title="Toluenesulfonic acid">toluenesulfonic acid</a> (tosylic acid). Unlike sulfuric acid itself, sulfonic acids can be solids. In fact, <a href="/wiki/Polystyrene" title="Polystyrene">polystyrene</a> functionalized into polystyrene sulfonate is a solid strongly acidic plastic that is filterable. </p><p><a href="/wiki/Superacid" title="Superacid">Superacids</a> are acids stronger than 100% sulfuric acid. Examples of superacids are <a href="/wiki/Fluoroantimonic_acid" title="Fluoroantimonic acid">fluoroantimonic acid</a>, <a href="/wiki/Magic_acid" title="Magic acid">magic acid</a> and <a href="/wiki/Perchloric_acid" title="Perchloric acid">perchloric acid</a>. The strongest known acid is <a href="/wiki/Helium_hydride_ion" title="Helium hydride ion">helium hydride ion</a>,<sup id="cite_ref-chebi33689_7-0" class="reference"><a href="#cite_note-chebi33689-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> with a <a href="/wiki/Proton_affinity" title="Proton affinity">proton affinity</a> of 177.8kJ/mol.<sup id="cite_ref-Epa_8-0" class="reference"><a href="#cite_note-Epa-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> Superacids can permanently protonate water to give ionic, crystalline <a href="/wiki/Hydronium" title="Hydronium">hydronium</a> "salts". They can also quantitatively stabilize <a href="/wiki/Carbocation" title="Carbocation">carbocations</a>. </p><p>While <i>K</i><sub>a</sub> measures the strength of an acid compound, the strength of an aqueous acid solution is measured by pH, which is an indication of the concentration of hydronium in the solution. The pH of a simple solution of an acid compound in water is determined by the dilution of the compound and the compound's <i>K</i><sub>a</sub>. </p> <div class="mw-heading mw-heading2"><h2 id="Lewis_acid_strength_in_non-aqueous_solutions">Lewis acid strength in non-aqueous solutions</h2></div> <p><a href="/wiki/Lewis_acids" class="mw-redirect" title="Lewis acids">Lewis acids</a> have been classified in the <a href="/wiki/ECW_model" title="ECW model">ECW model</a> and it has been shown that there is no one order of acid strengths.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> The relative acceptor strength of Lewis acids toward a series of bases, versus other Lewis acids, can be illustrated by <a href="/wiki/ECW_model" title="ECW model">C-B plots</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup> It has been shown that to define the order of Lewis acid strength at least two properties must be considered. For Pearson's qualitative <a href="/wiki/HSAB_theory" title="HSAB theory">HSAB theory</a> the two properties are <a href="/wiki/HSAB_theory" title="HSAB theory">hardness</a> and strength while for Drago's quantitative <a href="/wiki/ECW_model" title="ECW model">ECW model</a> the two properties are electrostatic and covalent. </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_characteristics">Chemical characteristics</h2></div> <div class="mw-heading mw-heading3"><h3 id="Monoprotic_acids">Monoprotic acids</h3></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/Acid_dissociation_constant#Monoprotic_acids" title="Acid dissociation constant">Acid dissociation constant §&#160;Monoprotic acids</a></div> <p>Monoprotic acids, also known as monobasic acids, are those acids that are able to donate one <a href="/wiki/Proton" title="Proton">proton</a> per molecule during the process of <a href="/wiki/Dissociation_(chemistry)" title="Dissociation (chemistry)">dissociation</a> (sometimes called ionization) as shown below (symbolized by HA): </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HA (aq) + H<sub class="template-chem2-sub">2</sub>O (l) ⇌ H<sub class="template-chem2-sub">3</sub>O<sup class="template-chem2-sup">+</sup> (aq) + A<sup class="template-chem2-sup">−</sup> (aq)</span> &#160;&#160;&#160;&#160; <i>K</i><sub>a</sub></dd></dl> <p>Common examples of monoprotic acids in <a href="/wiki/Mineral_acid" title="Mineral acid">mineral acids</a> include <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> (HCl) and <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a> (HNO<sub>3</sub>). On the other hand, for <a href="/wiki/Organic_acids" class="mw-redirect" title="Organic acids">organic acids</a> the term mainly indicates the presence of one <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> group and sometimes these acids are known as monocarboxylic acid. Examples in <a href="/wiki/Organic_acids" class="mw-redirect" title="Organic acids">organic acids</a> include <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a> (HCOOH), <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> (CH<sub>3</sub>COOH) and <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a> (C<sub>6</sub>H<sub>5</sub>COOH). </p> <div class="mw-heading mw-heading3"><h3 id="Polyprotic_acids">Polyprotic acids</h3></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/Acid_dissociation_constant#Polyprotic_acids" title="Acid dissociation constant">Acid dissociation constant §&#160;Polyprotic acids</a></div> <p>Polyprotic acids, also known as polybasic acids, are able to donate more than one proton per acid molecule, in contrast to monoprotic acids that only donate one proton per molecule. Specific types of polyprotic acids have more specific names, such as diprotic (or dibasic) acid (two potential protons to donate), and triprotic (or tribasic) acid (three potential protons to donate). Some macromolecules such as proteins and nucleic acids can have a very large number of acidic protons.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> </p><p>A diprotic acid (here symbolized by H<sub>2</sub>A) can undergo one or two dissociations depending on the pH. Each dissociation has its own dissociation constant, K<sub>a1</sub> and K<sub>a2</sub>. </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>A (aq) + H<sub class="template-chem2-sub">2</sub>O (l) ⇌ H<sub class="template-chem2-sub">3</sub>O<sup class="template-chem2-sup">+</sup> (aq) + HA<sup class="template-chem2-sup">−</sup> (aq)</span> &#160;&#160;&#160; <i>K</i><sub>a1</sub></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HA<sup class="template-chem2-sup">−</sup> (aq) + H<sub class="template-chem2-sub">2</sub>O (l) ⇌ H<sub class="template-chem2-sub">3</sub>O<sup class="template-chem2-sup">+</sup> (aq) + A<sup>2−</sup> (aq)</span> &#160;&#160;&#160; &#160; <i>K</i><sub>a2</sub></dd></dl> <p>The first dissociation constant is typically greater than the second (i.e., <i>K</i><sub>a1</sub> &gt; <i>K</i><sub>a2</sub>). For example, <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> (H<sub>2</sub>SO<sub>4</sub>) can donate one proton to form the <a href="/wiki/Bisulfate" class="mw-redirect" title="Bisulfate">bisulfate</a> anion (HSO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span>), for which <i>K</i><sub>a1</sub> is very large; then it can donate a second proton to form the <a href="/wiki/Sulfate" title="Sulfate">sulfate</a> anion (SO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span>), wherein the <i>K</i><sub>a2</sub> is intermediate strength. The large <i>K</i><sub>a1</sub> for the first dissociation makes sulfuric a strong acid. In a similar manner, the weak unstable <a href="/wiki/Carbonic_acid" title="Carbonic acid">carbonic acid</a> <span class="nowrap">(H<sub>2</sub>CO<sub>3</sub>)</span> can lose one proton to form <a href="/wiki/Bicarbonate" title="Bicarbonate">bicarbonate</a> anion <span class="nowrap">(HCO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>)</span> and lose a second to form <a href="/wiki/Carbonate" title="Carbonate">carbonate</a> anion (CO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>). Both <i>K</i><sub>a</sub> values are small, but <i>K</i><sub>a1</sub> &gt; <i>K</i><sub>a2</sub> . </p><p>A triprotic acid (H<sub>3</sub>A) can undergo one, two, or three dissociations and has three dissociation constants, where <i>K</i><sub>a1</sub> &gt; <i>K</i><sub>a2</sub> &gt; <i>K</i><sub>a3</sub>. </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>A (aq) + H<sub class="template-chem2-sub">2</sub>O (l) ⇌ H<sub class="template-chem2-sub">3</sub>O<sup class="template-chem2-sup">+</sup> (aq) + H<sub class="template-chem2-sub">2</sub>A<sup class="template-chem2-sup">−</sup> (aq)</span> &#160;&#160;&#160;&#160; <i>K</i><sub>a1</sub></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>A<sup class="template-chem2-sup">−</sup> (aq) + H<sub class="template-chem2-sub">2</sub>O (l) ⇌ H<sub class="template-chem2-sub">3</sub>O<sup class="template-chem2-sup">+</sup> (aq) + HA<sup>2−</sup> (aq)</span> &#160; &#160; &#160; <i>K</i><sub>a2</sub></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HA<sup>2−</sup> (aq) + H<sub class="template-chem2-sub">2</sub>O (l) ⇌ H<sub class="template-chem2-sub">3</sub>O<sup class="template-chem2-sup">+</sup> (aq) + A<sup>3−</sup> (aq)</span> &#160; &#160;&#160; <i>K</i><sub>a3</sub></dd></dl> <p>An <a href="/wiki/Inorganic" class="mw-redirect" title="Inorganic">inorganic</a> example of a triprotic acid is orthophosphoric acid (H<sub>3</sub>PO<sub>4</sub>), usually just called <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a>. All three protons can be successively lost to yield H<sub>2</sub>PO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span>, then HPO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span>, and finally PO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">3−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span>, the orthophosphate ion, usually just called <a href="/wiki/Phosphate" title="Phosphate">phosphate</a>. Even though the positions of the three protons on the original phosphoric acid molecule are equivalent, the successive <i>K</i><sub>a</sub> values differ since it is energetically less favorable to lose a proton if the conjugate base is more negatively charged. An <a href="/wiki/Organic_compound" title="Organic compound">organic</a> example of a triprotic acid is <a href="/wiki/Citric_acid" title="Citric acid">citric acid</a>, which can successively lose three protons to finally form the <a href="/wiki/Citrate" class="mw-redirect" title="Citrate">citrate</a> ion. </p><p>Although the subsequent loss of each hydrogen ion is less favorable, all of the conjugate bases are present in solution. The fractional concentration, <i>α</i> (alpha), for each species can be calculated. For example, a generic diprotic acid will generate 3 species in solution: H<sub>2</sub>A, HA<sup>−</sup>, and A<sup>2−</sup>. The fractional concentrations can be calculated as below when given either the pH (which can be converted to the [H<sup>+</sup>]) or the concentrations of the acid with all its conjugate bases: </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 {\begin{aligned}\alpha _{{\ce {H2A}}}&amp;={\frac {{\ce {[H+]^2}}}{{\ce {[H+]^2}}+[{\ce {H+}}]K_{1}+K_{1}K_{2}}}={\frac {{\ce {[H2A]}}}{{\ce {{[H2A]}}}+[HA^{-}]+[A^{2-}]}}\\\alpha _{{\ce {HA^-}}}&amp;={\frac {[{\ce {H+}}]K_{1}}{{\ce {[H+]^2}}+[{\ce {H+}}]K_{1}+K_{1}K_{2}}}={\frac {{\ce {[HA^-]}}}{{\ce {[H2A]}}+{[HA^{-}]}+{[A^{2-}]}}}\\\alpha _{{\ce {A^{2-}}}}&amp;={\frac {K_{1}K_{2}}{{\ce {[H+]^2}}+[{\ce {H+}}]K_{1}+K_{1}K_{2}}}={\frac {{\ce {[A^{2-}]}}}{{\ce {{[H2A]}}}+{[HA^{-}]}+{[A^{2-}]}}}\end{aligned}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtable columnalign="right left right left right left right left right left right left" rowspacing="3pt" columnspacing="0em 2em 0em 2em 0em 2em 0em 2em 0em 2em 0em" displaystyle="true"> <mtr> <mtd> <msub> <mi>&#x03B1;<!-- α --></mi> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>A</mtext> </mrow> </mrow> </msub> </mtd> <mtd> <mi></mi> <mo>=</mo> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mrow class="MJX-TeXAtom-ORD"> <msup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> <mo stretchy="false">]</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msup> </mrow> <mrow> <mrow class="MJX-TeXAtom-ORD"> <msup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> <mo stretchy="false">]</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msup> </mrow> <mo>+</mo> <mo stretchy="false">[</mo> <mrow class="MJX-TeXAtom-ORD"> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> </mrow> <mo stretchy="false">]</mo> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> </msub> <mo>+</mo> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> </msub> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> </mrow> </mfrac> </mrow> <mo>=</mo> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>A</mtext> <mo stretchy="false">]</mo> </mrow> </mrow> <mrow> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>A</mtext> <mo stretchy="false">]</mo> </mrow> </mrow> </mrow> <mo>+</mo> <mo stretchy="false">[</mo> <mi>H</mi> <msup> <mi>A</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> <mo stretchy="false">]</mo> <mo>+</mo> <mo stretchy="false">[</mo> <msup> <mi>A</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> <mo stretchy="false">]</mo> </mrow> </mfrac> </mrow> </mtd> </mtr> <mtr> <mtd> <msub> <mi>&#x03B1;<!-- α --></mi> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <msup> <mtext>HA</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> </mrow> </mrow> </msub> </mtd> <mtd> <mi></mi> <mo>=</mo> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mrow> <mo stretchy="false">[</mo> <mrow class="MJX-TeXAtom-ORD"> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> </mrow> <mo stretchy="false">]</mo> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> </msub> </mrow> <mrow> <mrow class="MJX-TeXAtom-ORD"> <msup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> <mo stretchy="false">]</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msup> </mrow> <mo>+</mo> <mo stretchy="false">[</mo> <mrow class="MJX-TeXAtom-ORD"> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> </mrow> <mo stretchy="false">]</mo> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> </msub> <mo>+</mo> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> </msub> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> </mrow> </mfrac> </mrow> <mo>=</mo> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mtext>HA</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>&#x2212;<!-- − --></mo> </mrow> <mo stretchy="false">]</mo> </mrow> </mrow> <mrow> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>A</mtext> <mo stretchy="false">]</mo> </mrow> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mi>H</mi> <msup> <mi>A</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> <mo stretchy="false">]</mo> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msup> <mi>A</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> <mo stretchy="false">]</mo> </mrow> </mrow> </mfrac> </mrow> </mtd> </mtr> <mtr> <mtd> <msub> <mi>&#x03B1;<!-- α --></mi> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <msup> <mtext>A</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mo>&#x2212;<!-- − --></mo> </mrow> </mrow> </msup> </mrow> </mrow> </msub> </mtd> <mtd> <mi></mi> <mo>=</mo> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mrow> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> </msub> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> </mrow> <mrow> <mrow class="MJX-TeXAtom-ORD"> <msup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> <mo stretchy="false">]</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msup> </mrow> <mo>+</mo> <mo stretchy="false">[</mo> <mrow class="MJX-TeXAtom-ORD"> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> </mrow> <mo stretchy="false">]</mo> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> </msub> <mo>+</mo> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> </msub> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> </mrow> </mfrac> </mrow> <mo>=</mo> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msup> <mtext>A</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mo>&#x2212;<!-- − --></mo> </mrow> </mrow> </msup> <mo stretchy="false">]</mo> </mrow> </mrow> <mrow> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>A</mtext> <mo stretchy="false">]</mo> </mrow> </mrow> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mi>H</mi> <msup> <mi>A</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> <mo stretchy="false">]</mo> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msup> <mi>A</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> <mo stretchy="false">]</mo> </mrow> </mrow> </mfrac> </mrow> </mtd> </mtr> </mtable> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\begin{aligned}\alpha _{{\ce {H2A}}}&amp;={\frac {{\ce {[H+]^2}}}{{\ce {[H+]^2}}+[{\ce {H+}}]K_{1}+K_{1}K_{2}}}={\frac {{\ce {[H2A]}}}{{\ce {{[H2A]}}}+[HA^{-}]+[A^{2-}]}}\\\alpha _{{\ce {HA^-}}}&amp;={\frac {[{\ce {H+}}]K_{1}}{{\ce {[H+]^2}}+[{\ce {H+}}]K_{1}+K_{1}K_{2}}}={\frac {{\ce {[HA^-]}}}{{\ce {[H2A]}}+{[HA^{-}]}+{[A^{2-}]}}}\\\alpha _{{\ce {A^{2-}}}}&amp;={\frac {K_{1}K_{2}}{{\ce {[H+]^2}}+[{\ce {H+}}]K_{1}+K_{1}K_{2}}}={\frac {{\ce {[A^{2-}]}}}{{\ce {{[H2A]}}}+{[HA^{-}]}+{[A^{2-}]}}}\end{aligned}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/8e09f46996e12e5d2c821158e6bc6f70f54edbe7" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -10.838ex; width:62.416ex; height:22.843ex;" alt="{\displaystyle {\begin{aligned}\alpha _{{\ce {H2A}}}&amp;={\frac {{\ce {[H+]^2}}}{{\ce {[H+]^2}}+[{\ce {H+}}]K_{1}+K_{1}K_{2}}}={\frac {{\ce {[H2A]}}}{{\ce {{[H2A]}}}+[HA^{-}]+[A^{2-}]}}\\\alpha _{{\ce {HA^-}}}&amp;={\frac {[{\ce {H+}}]K_{1}}{{\ce {[H+]^2}}+[{\ce {H+}}]K_{1}+K_{1}K_{2}}}={\frac {{\ce {[HA^-]}}}{{\ce {[H2A]}}+{[HA^{-}]}+{[A^{2-}]}}}\\\alpha _{{\ce {A^{2-}}}}&amp;={\frac {K_{1}K_{2}}{{\ce {[H+]^2}}+[{\ce {H+}}]K_{1}+K_{1}K_{2}}}={\frac {{\ce {[A^{2-}]}}}{{\ce {{[H2A]}}}+{[HA^{-}]}+{[A^{2-}]}}}\end{aligned}}}"></span></dd></dl> <p>A plot of these fractional concentrations against pH, for given <i>K</i><sub>1</sub> and <i>K</i><sub>2</sub>, is known as a <a href="/wiki/Bjerrum_plot" title="Bjerrum plot">Bjerrum plot</a>. A pattern is observed in the above equations and can be expanded to the general <i>n</i> -protic acid that has been deprotonated <i>i</i> -times: </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 \alpha _{{\ce {H}}_{n-i}A^{i-}}={{[{\ce {H+}}]^{n-i}\displaystyle \prod _{j=0}^{i}K_{j}} \over {\displaystyle \sum _{i=0}^{n}{\Big [}[{\ce {H+}}]^{n-i}\displaystyle \prod _{j=0}^{i}K_{j}}{\Big ]}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <msub> <mi>&#x03B1;<!-- α --></mi> <mrow class="MJX-TeXAtom-ORD"> <msub> <mrow class="MJX-TeXAtom-ORD"> <mtext>H</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>n</mi> <mo>&#x2212;<!-- − --></mo> <mi>i</mi> </mrow> </msub> <msup> <mi>A</mi> <mrow class="MJX-TeXAtom-ORD"> <mi>i</mi> <mo>&#x2212;<!-- − --></mo> </mrow> </msup> </mrow> </msub> <mo>=</mo> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mrow class="MJX-TeXAtom-ORD"> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> </mrow> <msup> <mo stretchy="false">]</mo> <mrow class="MJX-TeXAtom-ORD"> <mi>n</mi> <mo>&#x2212;<!-- − --></mo> <mi>i</mi> </mrow> </msup> <mstyle displaystyle="true" scriptlevel="0"> <munderover> <mo>&#x220F;<!-- ∏ --></mo> <mrow class="MJX-TeXAtom-ORD"> <mi>j</mi> <mo>=</mo> <mn>0</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>i</mi> </mrow> </munderover> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mi>j</mi> </mrow> </msub> </mstyle> </mrow> <mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <munderover> <mo>&#x2211;<!-- ∑ --></mo> <mrow class="MJX-TeXAtom-ORD"> <mi>i</mi> <mo>=</mo> <mn>0</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>n</mi> </mrow> </munderover> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo maxsize="1.623em" minsize="1.623em">[</mo> </mrow> </mrow> <mo stretchy="false">[</mo> <mrow class="MJX-TeXAtom-ORD"> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> </mrow> <msup> <mo stretchy="false">]</mo> <mrow class="MJX-TeXAtom-ORD"> <mi>n</mi> <mo>&#x2212;<!-- − --></mo> <mi>i</mi> </mrow> </msup> <mstyle displaystyle="true" scriptlevel="0"> <munderover> <mo>&#x220F;<!-- ∏ --></mo> <mrow class="MJX-TeXAtom-ORD"> <mi>j</mi> <mo>=</mo> <mn>0</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>i</mi> </mrow> </munderover> <msub> <mi>K</mi> <mrow class="MJX-TeXAtom-ORD"> <mi>j</mi> </mrow> </msub> </mstyle> </mstyle> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo maxsize="1.623em" minsize="1.623em">]</mo> </mrow> </mrow> </mrow> </mfrac> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \alpha _{{\ce {H}}_{n-i}A^{i-}}={{[{\ce {H+}}]^{n-i}\displaystyle \prod _{j=0}^{i}K_{j}} \over {\displaystyle \sum _{i=0}^{n}{\Big [}[{\ce {H+}}]^{n-i}\displaystyle \prod _{j=0}^{i}K_{j}}{\Big ]}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/5a82c39009cacb7d891f1f06a46a6558c3c91e76" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -7.338ex; width:32.421ex; height:15.843ex;" alt="{\displaystyle \alpha _{{\ce {H}}_{n-i}A^{i-}}={{[{\ce {H+}}]^{n-i}\displaystyle \prod _{j=0}^{i}K_{j}} \over {\displaystyle \sum _{i=0}^{n}{\Big [}[{\ce {H+}}]^{n-i}\displaystyle \prod _{j=0}^{i}K_{j}}{\Big ]}}}"></span></dd></dl> <p>where <i>K</i><sub>0</sub> = 1 and the other K-terms are the dissociation constants for the acid. </p> <div class="mw-heading mw-heading3"><h3 id="Neutralization">Neutralization</h3></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Hydrochloric_acid_ammonia.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Hydrochloric_acid_ammonia.jpg/220px-Hydrochloric_acid_ammonia.jpg" decoding="async" width="220" height="216" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/a/a0/Hydrochloric_acid_ammonia.jpg 1.5x" data-file-width="301" data-file-height="296" /></a><figcaption><a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">Hydrochloric acid</a> (in <a href="/wiki/Beaker_(glassware)" class="mw-redirect" title="Beaker (glassware)">beaker</a>) reacting with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> fumes to produce <a href="/wiki/Ammonium_chloride" title="Ammonium chloride">ammonium chloride</a> (white smoke).</figcaption></figure> <p><a href="/wiki/Neutralization_(chemistry)" title="Neutralization (chemistry)">Neutralization</a> is the reaction between an acid and a base, producing a <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> and neutralized base; for example, <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> and <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> form <a href="/wiki/Sodium_chloride" title="Sodium chloride">sodium chloride</a> and water: </p> <dl><dd>HCl<sub>(aq)</sub> + NaOH<sub>(aq)</sub> → H<sub>2</sub>O<sub>(l)</sub> + NaCl<sub>(aq)</sub></dd></dl> <p>Neutralization is the basis of <a href="/wiki/Titration" title="Titration">titration</a>, where a <a href="/wiki/PH_indicator" title="PH indicator">pH indicator</a> shows equivalence point when the equivalent number of moles of a base have been added to an acid. It is often wrongly assumed that neutralization should result in a solution with pH 7.0, which is only the case with similar acid and base strengths during a reaction. </p><p>Neutralization with a base weaker than the acid results in a weakly acidic salt. An example is the weakly acidic <a href="/wiki/Ammonium_chloride" title="Ammonium chloride">ammonium chloride</a>, which is produced from the strong acid <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a> and the weak base <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>. Conversely, neutralizing a weak acid with a strong base gives a weakly basic salt (e.g., <a href="/wiki/Sodium_fluoride" title="Sodium fluoride">sodium fluoride</a> from <a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">hydrogen fluoride</a> and <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a>). </p> <div class="mw-heading mw-heading3"><h3 id="Weak_acid–weak_base_equilibrium"><span id="Weak_acid.E2.80.93weak_base_equilibrium"></span>Weak acid–weak base equilibrium</h3></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Henderson%E2%80%93Hasselbalch_equation" title="Henderson–Hasselbalch equation">Henderson–Hasselbalch equation</a></div> <p>In order for a protonated acid to lose a proton, the pH of the system must rise above the p<i>K</i><sub>a</sub> of the acid. The decreased concentration of H<sup>+</sup> in that basic solution shifts the equilibrium towards the conjugate base form (the deprotonated form of the acid). In lower-pH (more acidic) solutions, there is a high enough H<sup>+</sup> concentration in the solution to cause the acid to remain in its protonated form. </p><p>Solutions of weak acids and salts of their conjugate bases form <a href="/wiki/Buffer_solution" title="Buffer solution">buffer solutions</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Titration">Titration</h2></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Acid%E2%80%93base_titration" title="Acid–base titration">Acid–base titration</a></div> <p>To determine the concentration of an acid in an aqueous solution, an acid–base titration is commonly performed. A strong base solution with a known concentration, usually NaOH or KOH, is added to neutralize the acid solution according to the color change of the indicator with the amount of base added.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup> The titration curve of an acid titrated by a base has two axes, with the base volume on the x-axis and the solution's pH value on the y-axis. The pH of the solution always goes up as the base is added to the solution. </p> <div class="mw-heading mw-heading3"><h3 id="Example:_Diprotic_acid">Example: Diprotic acid</h3></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Titration_alanine.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Titration_alanine.jpg/220px-Titration_alanine.jpg" decoding="async" width="220" height="267" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Titration_alanine.jpg/330px-Titration_alanine.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Titration_alanine.jpg/440px-Titration_alanine.jpg 2x" data-file-width="577" data-file-height="700" /></a><figcaption>This is an ideal titration curve for <a href="/wiki/Alanine" title="Alanine">alanine</a>, a diprotic amino acid.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> Point 2 is the first equivalent point where the amount of NaOH added equals the amount of alanine in the original solution.</figcaption></figure> <p>For each diprotic acid titration curve, from left to right, there are two midpoints, two equivalence points, and two buffer regions.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Equivalence_points">Equivalence points</h4></div> <p>Due to the successive dissociation processes, there are two equivalence points in the titration curve of a diprotic acid.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup> The first equivalence point occurs when all first hydrogen ions from the first ionization are titrated.<sup id="cite_ref-learning_17-0" class="reference"><a href="#cite_note-learning-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> In other words, the amount of OH<sup>−</sup> added equals the original amount of H<sub>2</sub>A at the first equivalence point. The second equivalence point occurs when all hydrogen ions are titrated. Therefore, the amount of OH<sup>−</sup> added equals twice the amount of H<sub>2</sub>A at this time. For a weak diprotic acid titrated by a strong base, the second equivalence point must occur at pH above 7 due to the hydrolysis of the resulted salts in the solution.<sup id="cite_ref-learning_17-1" class="reference"><a href="#cite_note-learning-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> At either equivalence point, adding a drop of base will cause the steepest rise of the pH value in the system. </p> <div class="mw-heading mw-heading4"><h4 id="Buffer_regions_and_midpoints">Buffer regions and midpoints</h4></div> <p>A titration curve for a diprotic acid contains two midpoints where pH=pK<sub>a</sub>. Since there are two different K<sub>a</sub> values, the first midpoint occurs at pH=pK<sub>a1</sub> and the second one occurs at pH=pK<sub>a2</sub>.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup> Each segment of the curve that contains a midpoint at its center is called the buffer region. Because the buffer regions consist of the acid and its conjugate base, it can resist pH changes when base is added until the next equivalent points.<sup id="cite_ref-Ebbing_5-3" class="reference"><a href="#cite_note-Ebbing-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications_of_acids">Applications of acids</h2></div> <div class="mw-heading mw-heading3"><h3 id="In_industry">In industry</h3></div> <p>Acids are fundamental reagents in treating almost all processes in modern industry. Sulfuric acid, a diprotic acid, is the most widely used acid in industry, and is also the most-produced industrial chemical in the world. It is mainly used in producing fertilizer, detergent, batteries and dyes, as well as used in processing many products such like removing impurities.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup> According to the statistics data in 2011, the annual production of sulfuric acid was around 200 million tonnes in the world.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup> For example, phosphate minerals react with sulfuric acid to produce <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a> for the production of phosphate fertilizers, and <a href="/wiki/Zinc" title="Zinc">zinc</a> is produced by dissolving zinc oxide into sulfuric acid, purifying the solution and electrowinning. </p><p>In the chemical industry, acids react in neutralization reactions to produce salts. For example, <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a> reacts with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> to produce <a href="/wiki/Ammonium_nitrate" title="Ammonium nitrate">ammonium nitrate</a>, a fertilizer. Additionally, <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> can be <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">esterified</a> with alcohols, to produce <a href="/wiki/Ester" title="Ester">esters</a>. </p><p>Acids are often used to remove rust and other corrosion from metals in a process known as <a href="/wiki/Pickling_(metal)" title="Pickling (metal)">pickling</a>. They may be used as an electrolyte in a <a href="/wiki/Wet_cell_battery" class="mw-redirect" title="Wet cell battery">wet cell battery</a>, such as <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> in a <a href="/wiki/Car_battery" class="mw-redirect" title="Car battery">car battery</a>. </p> <div class="mw-heading mw-heading3"><h3 id="In_food">In food</h3></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Tumbler_of_cola_with_ice.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Tumbler_of_cola_with_ice.jpg/220px-Tumbler_of_cola_with_ice.jpg" decoding="async" width="220" height="301" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Tumbler_of_cola_with_ice.jpg/330px-Tumbler_of_cola_with_ice.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Tumbler_of_cola_with_ice.jpg/440px-Tumbler_of_cola_with_ice.jpg 2x" data-file-width="489" data-file-height="670" /></a><figcaption>Carbonated water (H<sub>2</sub>CO<sub>3</sub> aqueous solution) is commonly added to soft drinks to make them effervesce.</figcaption></figure> <p><a href="/wiki/Tartaric_acid" title="Tartaric acid">Tartaric acid</a> is an important component of some commonly used foods like unripened mangoes and tamarind. Natural fruits and vegetables also contain acids. <a href="/wiki/Citric_acid" title="Citric acid">Citric acid</a> is present in oranges, lemon and other citrus fruits. <a href="/wiki/Oxalic_acid" title="Oxalic acid">Oxalic acid</a> is present in tomatoes, spinach, and especially in <a href="/wiki/Carambola" title="Carambola">carambola</a> and <a href="/wiki/Rhubarb" title="Rhubarb">rhubarb</a>; rhubarb leaves and unripe carambolas are toxic because of high concentrations of oxalic acid. <a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">Ascorbic acid</a> (Vitamin C) is an essential vitamin for the human body and is present in such foods as amla (<a href="/wiki/Phyllanthus_emblica" title="Phyllanthus emblica">Indian gooseberry</a>), lemon, citrus fruits, and guava. </p><p>Many acids can be found in various kinds of food as additives, as they alter their taste and serve as preservatives. <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">Phosphoric acid</a>, for example, is a component of <a href="/wiki/Cola" title="Cola">cola</a> drinks. <a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a> is used in day-to-day life as vinegar. Citric acid is used as a preservative in sauces and pickles. </p><p><a href="/wiki/Carbonic_acid" title="Carbonic acid">Carbonic acid</a> is one of the most common acid additives that are widely added in <a href="/wiki/Soft_drink" title="Soft drink">soft drinks</a>. During the manufacturing process, CO<sub>2</sub> is usually pressurized to dissolve in these drinks to generate carbonic acid. Carbonic acid is very unstable and tends to decompose into water and CO<sub>2</sub> at room temperature and pressure. Therefore, when bottles or cans of these kinds of soft drinks are opened, the soft drinks fizz and effervesce as CO<sub>2</sub> bubbles come out.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup> </p><p>Certain acids are used as drugs. <a href="/wiki/Acetylsalicylic_acid" class="mw-redirect" title="Acetylsalicylic acid">Acetylsalicylic acid</a> (Aspirin) is used as a pain killer and for bringing down fevers. </p> <div class="mw-heading mw-heading3"><h3 id="In_human_bodies">In human bodies</h3></div> <p>Acids play important roles in the human body. The hydrochloric acid present in the stomach aids digestion by breaking down large and complex food molecules. Amino acids are required for synthesis of proteins required for growth and repair of body tissues. Fatty acids are also required for growth and repair of body tissues. Nucleic acids are important for the manufacturing of DNA and RNA and transmitting of traits to offspring through genes. Carbonic acid is important for maintenance of pH equilibrium in the body. </p><p>Human bodies contain a variety of organic and inorganic compounds, among those <a href="/wiki/Dicarboxylic_acid" title="Dicarboxylic acid">dicarboxylic acids</a> play an essential role in many biological behaviors. Many of those acids are <a href="/wiki/Amino_acids" class="mw-redirect" title="Amino acids">amino acids</a>, which mainly serve as materials for the synthesis of proteins.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup> Other weak acids serve as buffers with their conjugate bases to keep the body's pH from undergoing large scale changes that would be harmful to cells.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup> The rest of the dicarboxylic acids also participate in the synthesis of various biologically important compounds in human bodies. </p> <div class="mw-heading mw-heading3"><h3 id="Acid_catalysis">Acid catalysis</h3></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Acid_catalysis" title="Acid catalysis">Acid catalysis</a></div> <p>Acids are used as <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalysts</a> in industrial and organic chemistry; for example, <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> is used in very large quantities in the <a href="/wiki/Alkylation" title="Alkylation">alkylation</a> process to produce gasoline. Some acids, such as sulfuric, phosphoric, and hydrochloric acids, also effect <a href="/wiki/Dehydration_reaction" title="Dehydration reaction">dehydration</a> and <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation reactions</a>. In biochemistry, many <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> employ acid catalysis.<sup id="cite_ref-Voet_acid_cat_24-0" class="reference"><a href="#cite_note-Voet_acid_cat-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biological_occurrence">Biological occurrence</h2></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Aminoacid.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/3/34/Aminoacid.png" decoding="async" width="160" height="131" class="mw-file-element" data-file-width="160" data-file-height="131" /></a><figcaption>Basic structure of an <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a>.</figcaption></figure><p>Many biologically important molecules are acids. <a href="/wiki/Nucleic_acid" title="Nucleic acid">Nucleic acids</a>, which contain acidic <a href="/wiki/Phosphate" title="Phosphate">phosphate groups</a>, include <a href="/wiki/DNA" title="DNA">DNA</a> and <a href="/wiki/RNA" title="RNA">RNA</a>. Nucleic acids contain the genetic code that determines many of an organism's characteristics, and is passed from parents to offspring. DNA contains the chemical blueprint for the synthesis of <a href="/wiki/Protein" title="Protein">proteins</a>, which are made up of <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> subunits. <a href="/wiki/Cell_membrane" title="Cell membrane">Cell membranes</a> contain <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acid</a> <a href="/wiki/Ester" title="Ester">esters</a> such as <a href="/wiki/Phospholipids" class="mw-redirect" title="Phospholipids">phospholipids</a>. </p><p>An α-amino acid has a central carbon (the α or <a href="/wiki/Alpha_and_beta_carbon" class="mw-redirect" title="Alpha and beta carbon"><i>alpha</i> carbon</a>) that is covalently bonded to a <a href="/wiki/Carboxyl" class="mw-redirect" title="Carboxyl">carboxyl</a> group (thus they are <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a>), an <a href="/wiki/Amine" title="Amine">amino</a> group, a hydrogen atom and a variable group. The variable group, also called the R group or side chain, determines the identity and many of the properties of a specific amino acid. In <a href="/wiki/Glycine" title="Glycine">glycine</a>, the simplest amino acid, the R group is a hydrogen atom, but in all other amino acids it is contains one or more carbon atoms bonded to hydrogens, and may contain other elements such as sulfur, oxygen or nitrogen. With the exception of glycine, naturally occurring amino acids are <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a> and almost invariably occur in the <a href="/wiki/Chirality_(chemistry)#By_configuration:_D-_and_L-" title="Chirality (chemistry)"><small>L</small>-configuration</a>. <a href="/wiki/Peptidoglycan" title="Peptidoglycan">Peptidoglycan</a>, found in some bacterial <a href="/wiki/Cell_wall" title="Cell wall">cell walls</a> contains some <small>D</small>-amino acids. At physiological pH, typically around 7, free amino acids exist in a charged form, where the acidic carboxyl group (-COOH) loses a proton (-COO<sup>−</sup>) and the basic amine group (-NH<sub>2</sub>) gains a proton (-NH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>). The entire molecule has a net neutral charge and is a <a href="/wiki/Zwitterion" title="Zwitterion">zwitterion</a>, with the exception of amino acids with basic or acidic side chains. <a href="/wiki/Aspartic_acid" title="Aspartic acid">Aspartic acid</a>, for example, possesses one protonated amine and two deprotonated carboxyl groups, for a net charge of −1 at physiological pH. </p><p>Fatty acids and fatty acid derivatives are another group of carboxylic acids that play a significant role in biology. These contain long hydrocarbon chains and a carboxylic acid group on one end. The cell membrane of nearly all organisms is primarily made up of a <a href="/wiki/Phospholipid_bilayer" class="mw-redirect" title="Phospholipid bilayer">phospholipid bilayer</a>, a <a href="/wiki/Micelle" title="Micelle">micelle</a> of hydrophobic fatty acid esters with polar, hydrophilic <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> "head" groups. Membranes contain additional components, some of which can participate in acid–base reactions. </p><p>In humans and many other animals, <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> is a part of the <a href="/wiki/Gastric_acid" title="Gastric acid">gastric acid</a> secreted within the <a href="/wiki/Stomach" title="Stomach">stomach</a> to help hydrolyze <a href="/wiki/Protein" title="Protein">proteins</a> and <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a>, as well as converting the inactive pro-enzyme, <a href="/wiki/Pepsinogen" class="mw-redirect" title="Pepsinogen">pepsinogen</a> into the <a href="/wiki/Digestive_enzyme" title="Digestive enzyme">enzyme</a>, <a href="/wiki/Pepsin" title="Pepsin">pepsin</a>. Some organisms produce acids for defense; for example, ants produce <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>. </p><p>Acid–base equilibrium plays a critical role in regulating <a href="/wiki/Mammal" title="Mammal">mammalian</a> breathing. <a href="/wiki/Molecular_oxygen" class="mw-redirect" title="Molecular oxygen">Oxygen</a> gas (O<sub>2</sub>) drives <a href="/wiki/Cellular_respiration" title="Cellular respiration">cellular respiration</a>, the process by which animals release the chemical <a href="/wiki/Potential_energy" title="Potential energy">potential energy</a> stored in food, producing <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> (CO<sub>2</sub>) as a byproduct. Oxygen and carbon dioxide are exchanged in the <a href="/wiki/Lungs" class="mw-redirect" title="Lungs">lungs</a>, and the body responds to changing energy demands by adjusting the rate of <a href="/wiki/Ventilation_(physiology)" class="mw-redirect" title="Ventilation (physiology)">ventilation</a>. For example, during periods of exertion the body rapidly breaks down stored <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> and fat, releasing CO<sub>2</sub> into the blood stream. In aqueous solutions such as blood CO<sub>2</sub> exists in equilibrium with <a href="/wiki/Carbonic_acid" title="Carbonic acid">carbonic acid</a> and <a href="/wiki/Bicarbonate" title="Bicarbonate">bicarbonate</a> ion. </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CO<sub class="template-chem2-sub">2</sub> + H<sub class="template-chem2-sub">2</sub>O ⇌ H<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">3</sub> ⇌ H<sup class="template-chem2-sup">+</sup> + HCO<span class="template-chem2-su"><span>−</span><span>3</span></span></span></dd></dl> <p>It is the decrease in pH that signals the brain to breathe faster and deeper, expelling the excess CO<sub>2</sub> and resupplying the cells with O<sub>2</sub>. </p> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Aspirin-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Aspirin-skeletal.svg/220px-Aspirin-skeletal.svg.png" decoding="async" width="220" height="183" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Aspirin-skeletal.svg/330px-Aspirin-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/67/Aspirin-skeletal.svg/440px-Aspirin-skeletal.svg.png 2x" data-file-width="336" data-file-height="279" /></a><figcaption><a href="/wiki/Aspirin" title="Aspirin">Aspirin</a> (acetylsalicylic acid) is a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a></figcaption></figure> <p><a href="/wiki/Cell_membrane" title="Cell membrane">Cell membranes</a> are generally impermeable to charged or large, polar molecules because of the <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilic</a> fatty acyl chains comprising their interior. Many biologically important molecules, including a number of pharmaceutical agents, are organic weak acids that can cross the membrane in their protonated, uncharged form but not in their charged form (i.e., as the conjugate base). For this reason the activity of many drugs can be enhanced or inhibited by the use of antacids or acidic foods. The charged form, however, is often more soluble in blood and <a href="/wiki/Cytosol" title="Cytosol">cytosol</a>, both aqueous environments. When the extracellular environment is more acidic than the neutral pH within the cell, certain acids will exist in their neutral form and will be membrane soluble, allowing them to cross the phospholipid bilayer. Acids that lose a proton at the <a href="/wiki/Intracellular_pH" title="Intracellular pH">intracellular pH</a> will exist in their soluble, charged form and are thus able to diffuse through the cytosol to their target. <a href="/wiki/Ibuprofen" title="Ibuprofen">Ibuprofen</a>, <a href="/wiki/Aspirin" title="Aspirin">aspirin</a> and <a href="/wiki/Penicillin" title="Penicillin">penicillin</a> are examples of drugs that are weak acids. </p><div class="mw-heading mw-heading2"><h2 id="Common_acids">Common acids</h2></div> <div class="mw-heading mw-heading3"><h3 id="Mineral_acids_(inorganic_acids)"><span id="Mineral_acids_.28inorganic_acids.29"></span>Mineral acids (inorganic acids)</h3></div> <ul><li><a href="/wiki/Hydrogen_halides" class="mw-redirect" title="Hydrogen halides">Hydrogen halides</a> and their solutions: <a href="/wiki/Hydrofluoric_acid" title="Hydrofluoric acid">hydrofluoric acid</a> (HF), <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> (HCl), <a href="/wiki/Hydrobromic_acid" title="Hydrobromic acid">hydrobromic acid</a> (HBr), <a href="/wiki/Hydroiodic_acid" title="Hydroiodic acid">hydroiodic acid</a> (HI)</li> <li>Halogen oxoacids: <a href="/wiki/Hypochlorous_acid" title="Hypochlorous acid">hypochlorous acid</a> (HClO), <a href="/wiki/Chlorous_acid" title="Chlorous acid">chlorous acid</a> (HClO<sub>2</sub>), <a href="/wiki/Chloric_acid" title="Chloric acid">chloric acid</a> (HClO<sub>3</sub>), <a href="/wiki/Perchloric_acid" title="Perchloric acid">perchloric acid</a> (HClO<sub>4</sub>), and corresponding analogs for bromine and iodine <ul><li><a href="/wiki/Hypofluorous_acid" title="Hypofluorous acid">Hypofluorous acid</a> (HFO), the only known oxoacid for fluorine.</li></ul></li> <li><a href="/wiki/Sulfuric_acid" title="Sulfuric acid">Sulfuric acid</a> (H<sub>2</sub>SO<sub>4</sub>)</li> <li><a href="/wiki/Fluorosulfuric_acid" title="Fluorosulfuric acid">Fluorosulfuric acid</a> (HSO<sub>3</sub>F)</li> <li><a href="/wiki/Nitric_acid" title="Nitric acid">Nitric acid</a> (HNO<sub>3</sub>)</li> <li><a href="/wiki/Phosphoric_acid" title="Phosphoric acid">Phosphoric acid</a> (H<sub>3</sub>PO<sub>4</sub>)</li> <li><a href="/wiki/Fluoroantimonic_acid" title="Fluoroantimonic acid">Fluoroantimonic acid</a> (HSbF<sub>6</sub>)</li> <li><a href="/wiki/Fluoroboric_acid" title="Fluoroboric acid">Fluoroboric acid</a> (HBF<sub>4</sub>)</li> <li><a href="/wiki/Hexafluorophosphoric_acid" title="Hexafluorophosphoric acid">Hexafluorophosphoric acid</a> (HPF<sub>6</sub>)</li> <li><a href="/wiki/Chromic_acid" title="Chromic acid">Chromic acid</a> (H<sub>2</sub>CrO<sub>4</sub>)</li> <li><a href="/wiki/Boric_acid" title="Boric acid">Boric acid</a> (H<sub>3</sub>BO<sub>3</sub>)</li></ul> <div class="mw-heading mw-heading3"><h3 id="Sulfonic_acids">Sulfonic acids</h3></div> <p>A <a href="/wiki/Sulfonic_acid" title="Sulfonic acid">sulfonic acid</a> has the general formula RS(=O)<sub>2</sub>–OH, where R is an organic radical. </p> <ul><li><a href="/wiki/Methanesulfonic_acid" title="Methanesulfonic acid">Methanesulfonic acid</a> (or mesylic acid, CH<sub>3</sub>SO<sub>3</sub>H)</li> <li><a href="/wiki/Ethanesulfonic_acid" title="Ethanesulfonic acid">Ethanesulfonic acid</a> (or esylic acid, CH<sub>3</sub>CH<sub>2</sub>SO<sub>3</sub>H)</li> <li><a href="/wiki/Benzenesulfonic_acid" title="Benzenesulfonic acid">Benzenesulfonic acid</a> (or besylic acid, C<sub>6</sub>H<sub>5</sub>SO<sub>3</sub>H)</li> <li><a href="/wiki/P-Toluenesulfonic_acid" title="P-Toluenesulfonic acid">p-Toluenesulfonic acid</a> (or tosylic acid, CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>3</sub>H)</li> <li><a href="/wiki/Trifluoromethanesulfonic_acid" class="mw-redirect" title="Trifluoromethanesulfonic acid">Trifluoromethanesulfonic acid</a> (or triflic acid, CF<sub>3</sub>SO<sub>3</sub>H)</li> <li><a href="/wiki/Polystyrene_sulfonic_acid" class="mw-redirect" title="Polystyrene sulfonic acid">Polystyrene sulfonic acid</a> (sulfonated <a href="/wiki/Polystyrene" title="Polystyrene">polystyrene</a>, [CH<sub>2</sub>CH(C<sub>6</sub>H<sub>4</sub>)SO<sub>3</sub>H]<sub>n</sub>)</li></ul> <div class="mw-heading mw-heading3"><h3 id="Carboxylic_acids">Carboxylic acids</h3></div> <p>A <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> has the general formula R-C(O)OH, where R is an organic radical. The carboxyl group -C(O)OH contains a <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> group, C=O, and a <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> group, O-H. </p> <ul><li><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a> (CH<sub>3</sub>COOH)</li> <li><a href="/wiki/Citric_acid" title="Citric acid">Citric acid</a> (C<sub>6</sub>H<sub>8</sub>O<sub>7</sub>)</li> <li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a> (HCOOH)</li> <li><a href="/wiki/Gluconic_acid" title="Gluconic acid">Gluconic acid</a> HOCH<sub>2</sub>-(CHOH)<sub>4</sub>-COOH</li> <li><a href="/wiki/Lactic_acid" title="Lactic acid">Lactic acid</a> (CH<sub>3</sub>-CHOH-COOH)</li> <li><a href="/wiki/Oxalic_acid" title="Oxalic acid">Oxalic acid</a> (HOOC-COOH)</li> <li><a href="/wiki/Tartaric_acid" title="Tartaric acid">Tartaric acid</a> (HOOC-CHOH-CHOH-COOH)</li></ul> <div class="mw-heading mw-heading3"><h3 id="Halogenated_carboxylic_acids">Halogenated carboxylic acids</h3></div> <p>Halogenation at <a href="/wiki/Alpha_and_beta_carbon" class="mw-redirect" title="Alpha and beta carbon">alpha position</a> increases acid strength, so that the following acids are all stronger than acetic acid. </p> <ul><li><a href="/wiki/Fluoroacetic_acid" title="Fluoroacetic acid">Fluoroacetic acid</a></li> <li><a href="/wiki/Trifluoroacetic_acid" title="Trifluoroacetic acid">Trifluoroacetic acid</a></li> <li><a href="/wiki/Chloroacetic_acid" title="Chloroacetic acid">Chloroacetic acid</a></li> <li><a href="/wiki/Dichloroacetic_acid" title="Dichloroacetic acid">Dichloroacetic acid</a></li> <li><a href="/wiki/Trichloroacetic_acid" title="Trichloroacetic acid">Trichloroacetic acid</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Vinylogous_carboxylic_acids">Vinylogous carboxylic acids</h3></div> <p>Normal carboxylic acids are the direct union of a carbonyl group and a hydroxyl group. In <a href="/wiki/Vinylogous" class="mw-redirect" title="Vinylogous">vinylogous</a> carboxylic acids, a carbon-carbon double bond separates the carbonyl and hydroxyl groups. </p> <ul><li><a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">Ascorbic acid</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Nucleic_acids">Nucleic acids</h3></div> <ul><li><a href="/wiki/DNA" title="DNA">Deoxyribonucleic acid</a> (DNA)</li> <li><a href="/wiki/RNA" title="RNA">Ribonucleic acid</a> (RNA)</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2></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 reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-IUPAC_acid-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-IUPAC_acid_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IUPAC_acid_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-IUPAC_acid_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://goldbook.iupac.org/A00071.html">IUPAC Gold Book - acid</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"><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="CITEREFPetrucciHarwoodHerring2002" class="citation book cs1">Petrucci, R. 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Prentice Hall. p.&#160;146. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/0-13-014329-4" title="Special:BookSources/0-13-014329-4"><bdi>0-13-014329-4</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=General+Chemistry%3A+Principles+and+Modern+Applications&amp;rft.pages=146&amp;rft.edition=8th&amp;rft.pub=Prentice+Hall&amp;rft.date=2002&amp;rft.isbn=0-13-014329-4&amp;rft.aulast=Petrucci&amp;rft.aufirst=R.+H.&amp;rft.au=Harwood%2C+R.+S.&amp;rft.au=Herring%2C+F.+G.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.merriam-webster.com/dictionary/acid">Merriam-Webster's Online Dictionary: <i>acid</i></a></span> </li> <li id="cite_note-Oxtoby8th-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Oxtoby8th_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Oxtoby8th_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Oxtoby8th_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Oxtoby8th_4-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOtoxbyGillisButler2015" class="citation book cs1">Otoxby, D. 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Brooks Cole. p.&#160;617. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1305079113" title="Special:BookSources/978-1305079113"><bdi>978-1305079113</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=Principles+of+Modern+Chemistry&amp;rft.pages=617&amp;rft.edition=8th&amp;rft.pub=Brooks+Cole&amp;rft.date=2015&amp;rft.isbn=978-1305079113&amp;rft.aulast=Otoxby&amp;rft.aufirst=D.+W.&amp;rft.au=Gillis%2C+H.+P.&amp;rft.au=Butler%2C+L.+J.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-Ebbing-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ebbing_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ebbing_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ebbing_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Ebbing_5-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEbbingGammon2016" class="citation book cs1">Ebbing, Darrell; Gammon, Steven D. 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Cengage Learning. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9781305887299" title="Special:BookSources/9781305887299"><bdi>9781305887299</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=General+Chemistry&amp;rft.edition=11th&amp;rft.pub=Cengage+Learning&amp;rft.date=2016-01-01&amp;rft.isbn=9781305887299&amp;rft.aulast=Ebbing&amp;rft.aufirst=Darrell&amp;rft.au=Gammon%2C+Steven+D.&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBnccCgAAQBAJ&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStahlNakamo2008" class="citation book cs1">Stahl PH, Nakamo M (2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=IvSEXUZUON8C&amp;dq=%22free+acid%22+salt&amp;pg=PA92">"Pharmaceutical Aspects of the Salt Form"</a>. In Stahl PH, Warmth CG (eds.). <i>Handbook of Pharmaceutical Salts: Properties, Selection, and Use</i>. Weinheim: Wiley-VCH. pp.&#160;92–94. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-3-906390-58-1" title="Special:BookSources/978-3-906390-58-1"><bdi>978-3-906390-58-1</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=Pharmaceutical+Aspects+of+the+Salt+Form&amp;rft.btitle=Handbook+of+Pharmaceutical+Salts%3A+Properties%2C+Selection%2C+and+Use&amp;rft.place=Weinheim&amp;rft.pages=92-94&amp;rft.pub=Wiley-VCH&amp;rft.date=2008&amp;rft.isbn=978-3-906390-58-1&amp;rft.aulast=Stahl&amp;rft.aufirst=P.+Heinrich&amp;rft.au=Nakamo%2C+Masahiro&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DIvSEXUZUON8C%26dq%3D%2522free%2Bacid%2522%2Bsalt%26pg%3DPA92&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-chebi33689-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-chebi33689_7-0">^</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://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI%3A33689">"Hydridohelium (CHEBI:33689)"</a>. <i>Chemical Entities of Biological Interest (ChEBI)</i>. European Bioinformatics Institute.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Chemical+Entities+of+Biological+Interest+%28ChEBI%29&amp;rft.atitle=Hydridohelium+%28CHEBI%3A33689%29&amp;rft_id=https%3A%2F%2Fwww.ebi.ac.uk%2Fchebi%2FsearchId.do%3FchebiId%3DCHEBI%253A33689&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-Epa-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-Epa_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLiasLiebmanLevin1984" class="citation journal cs1">Lias, S. G.; Liebman, J. F.; Levin, R. D. (1984). "Evaluated Gas Phase Basicities and Proton Affinities of Molecules; Heats of Formation of Protonated Molecules". <i>Journal of Physical and Chemical Reference Data</i>. <b>13</b> (3): 695. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1984JPCRD..13..695L">1984JPCRD..13..695L</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1063%2F1.555719">10.1063/1.555719</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+Physical+and+Chemical+Reference+Data&amp;rft.atitle=Evaluated+Gas+Phase+Basicities+and+Proton+Affinities+of+Molecules%3B+Heats+of+Formation+of+Protonated+Molecules&amp;rft.volume=13&amp;rft.issue=3&amp;rft.pages=695&amp;rft.date=1984&amp;rft_id=info%3Adoi%2F10.1063%2F1.555719&amp;rft_id=info%3Abibcode%2F1984JPCRD..13..695L&amp;rft.aulast=Lias&amp;rft.aufirst=S.+G.&amp;rft.au=Liebman%2C+J.+F.&amp;rft.au=Levin%2C+R.+D.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVogel_G._C.Drago,_R._S.1996" class="citation journal cs1">Vogel G. C.; Drago, R. S. (1996). "The ECW Model". <i>Journal of Chemical Education</i>. <b>73</b> (8): 701–707. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1996JChEd..73..701V">1996JChEd..73..701V</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fed073p701">10.1021/ed073p701</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+Chemical+Education&amp;rft.atitle=The+ECW+Model&amp;rft.volume=73&amp;rft.issue=8&amp;rft.pages=701-707&amp;rft.date=1996&amp;rft_id=info%3Adoi%2F10.1021%2Fed073p701&amp;rft_id=info%3Abibcode%2F1996JChEd..73..701V&amp;rft.au=Vogel+G.+C.&amp;rft.au=Drago%2C+R.+S.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text">Laurence, C. and Gal, J-F. Lewis Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 ISBN 978-0-470-74957-9</span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCramer,_R._E.Bopp,_T._T.1977" class="citation journal cs1">Cramer, R. E.; Bopp, T. T. (1977). "Graphical display of the enthalpies of adduct formation for Lewis acids and bases". <i>Journal of Chemical Education</i>. <b>54</b>: 612–613. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fed054p612">10.1021/ed054p612</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+Chemical+Education&amp;rft.atitle=Graphical+display+of+the+enthalpies+of+adduct+formation+for+Lewis+acids+and+bases&amp;rft.volume=54&amp;rft.pages=612-613&amp;rft.date=1977&amp;rft_id=info%3Adoi%2F10.1021%2Fed054p612&amp;rft.au=Cramer%2C+R.+E.&amp;rft.au=Bopp%2C+T.+T.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span> The plots shown in this paper used older parameters. Improved E&amp;C parameters are listed in <a href="/wiki/ECW_model" title="ECW model">ECW model</a>.</span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWymanTileston_Edsall" class="citation book cs1">Wyman, Jeffries; Tileston Edsall, John. "Chapter 9: Polybasic Acids, Bases, and Ampholytes, Including Proteins". <i>Biophysical Chemistry - Volume 1</i>. p.&#160;477.</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=Chapter+9%3A+Polybasic+Acids%2C+Bases%2C+and+Ampholytes%2C+Including+Proteins&amp;rft.btitle=Biophysical+Chemistry+-+Volume+1&amp;rft.pages=477&amp;rft.aulast=Wyman&amp;rft.aufirst=Jeffries&amp;rft.au=Tileston+Edsall%2C+John&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFde_Levie1999" class="citation book cs1"><a href="/wiki/Robert_de_Levie" title="Robert de Levie">de Levie, Robert</a> (1999). <i>Aqueous Acid–Base Equilibria and Titrations</i>. 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"Assignment of the proton-association constants for 3-(3,4-dihydroxyphenyl)alanine (L-dopa)". <i>Journal of the Chemical Society, Dalton Transactions</i> (1): 43–45. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FDT9780000043">10.1039/DT9780000043</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+the+Chemical+Society%2C+Dalton+Transactions&amp;rft.atitle=Assignment+of+the+proton-association+constants+for+3-%283%2C4-dihydroxyphenyl%29alanine+%28L-dopa%29&amp;rft.issue=1&amp;rft.pages=43-45&amp;rft.date=1978&amp;rft_id=info%3Adoi%2F10.1039%2FDT9780000043&amp;rft.aulast=Jameson&amp;rft.aufirst=Reginald+F.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHelfferich1962" class="citation book cs1">Helfferich, Friedrich G. 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Courier Corporation. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9780486687841" title="Special:BookSources/9780486687841"><bdi>9780486687841</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=Ion+Exchange&amp;rft.pub=Courier+Corporation&amp;rft.date=1962-01-01&amp;rft.isbn=9780486687841&amp;rft.aulast=Helfferich&amp;rft.aufirst=Friedrich+G.&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DF9OQMEA88CAC&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</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://web.archive.org/web/20160207011433/http://dwb.unl.edu/calculators/activities/diproticacid.html">"Titration of Diprotic Acid"</a>. <i>dwb.unl.edu</i>. 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Retrieved <span class="nowrap">24 January</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=dwb.unl.edu&amp;rft.atitle=Titration+of+Diprotic+Acid&amp;rft_id=http%3A%2F%2Fdwb.unl.edu%2Fcalculators%2Factivities%2Fdiproticacid.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-learning-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-learning_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-learning_17-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKotzTreichelTownsendTreichel2014" class="citation book cs1">Kotz, John C.; Treichel, Paul M.; Townsend, John; Treichel, David (24 January 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=i1g8AwAAQBAJ"><i>Chemistry &amp; Chemical Reactivity</i></a>. Cengage Learning. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9781305176461" title="Special:BookSources/9781305176461"><bdi>9781305176461</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=Chemistry+%26+Chemical+Reactivity&amp;rft.pub=Cengage+Learning&amp;rft.date=2014-01-24&amp;rft.isbn=9781305176461&amp;rft.aulast=Kotz&amp;rft.aufirst=John+C.&amp;rft.au=Treichel%2C+Paul+M.&amp;rft.au=Townsend%2C+John&amp;rft.au=Treichel%2C+David&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Di1g8AwAAQBAJ&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLehningerNelsonCox2005" class="citation book cs1">Lehninger, Albert L.; Nelson, David L.; Cox, Michael M. 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Macmillan. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9780716743392" title="Special:BookSources/9780716743392"><bdi>9780716743392</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=Lehninger+Principles+of+Biochemistry&amp;rft.pub=Macmillan&amp;rft.date=2005-01-01&amp;rft.isbn=9780716743392&amp;rft.aulast=Lehninger&amp;rft.aufirst=Albert+L.&amp;rft.au=Nelson%2C+David+L.&amp;rft.au=Cox%2C+Michael+M.&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7chAN0UY0LYC&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</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="http://www.dummies.com/how-to/content/the-top-10-industrial-chemicals.html">"The Top 10 Industrial Chemicals - For Dummies"</a>. <i>dummies.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">5 February</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=dummies.com&amp;rft.atitle=The+Top+10+Industrial+Chemicals+-+For+Dummies&amp;rft_id=http%3A%2F%2Fwww.dummies.com%2Fhow-to%2Fcontent%2Fthe-top-10-industrial-chemicals.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</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="http://www.essentialchemicalindustry.org/chemicals/sulfuric-acid.html">"Sulfuric acid"</a>. <i>essentialchemicalindustry.org</i><span class="reference-accessdate">. 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Jr. (8 December 1981), <a rel="nofollow" class="external text" href="https://patents.google.com/patent/US4304736"><i>Method of and apparatus for making and dispensing a carbonated beverage utilizing propellant carbon dioxide gas for carbonating</i></a><span class="reference-accessdate">, retrieved <span class="nowrap">6 February</span> 2016</span></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=Method+of+and+apparatus+for+making+and+dispensing+a+carbonated+beverage+utilizing+propellant+carbon+dioxide+gas+for+carbonating&amp;rft.date=1981-12-08&amp;rft.aulast=McMillin&amp;rft.aufirst=John+R.&amp;rft.au=Tracy%2C+Gene+A.&amp;rft.au=Harvill%2C+William+A.&amp;rft.au=Credle%2C+William+S.+Jr.&amp;rft_id=https%3A%2F%2Fpatents.google.com%2Fpatent%2FUS4304736&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBarrettElmore2012" class="citation book cs1">Barrett, G. C.; Elmore, D. T. (June 2012). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160302214930/http://ebooks.cambridge.org/chapter.jsf?bid=CBO9781139163828&amp;cid=CBO9781139163828A114"><i>8 - Biological roles of amino acids and peptides - University Publishing Online</i></a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1017%2FCBO9781139163828">10.1017/CBO9781139163828</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9780521462921" title="Special:BookSources/9780521462921"><bdi>9780521462921</bdi></a>. Archived from <a rel="nofollow" class="external text" href="http://ebooks.cambridge.org/chapter.jsf?bid=CBO9781139163828&amp;cid=CBO9781139163828A114">the original</a> on 2 March 2016.</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=8+-+Biological+roles+of+amino+acids+and+peptides+-+University+Publishing+Online&amp;rft.date=2012-06&amp;rft_id=info%3Adoi%2F10.1017%2FCBO9781139163828&amp;rft.isbn=9780521462921&amp;rft.aulast=Barrett&amp;rft.aufirst=G.+C.&amp;rft.au=Elmore%2C+D.+T.&amp;rft_id=http%3A%2F%2Febooks.cambridge.org%2Fchapter.jsf%3Fbid%3DCBO9781139163828%26cid%3DCBO9781139163828A114&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGraham2006" class="citation web cs1">Graham, Timur (2006). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160213132105/http://fitsweb.uchc.edu/student/selectives/TimurGraham/Acid_Buffering.html">"Acid Buffering"</a>. <i>Acid Base Online Tutorial</i>. University of Connecticut. Archived from <a rel="nofollow" class="external text" href="http://fitsweb.uchc.edu/student/selectives/TimurGraham/Acid_Buffering.html">the original</a> on 13 February 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">6 February</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Acid+Base+Online+Tutorial&amp;rft.atitle=Acid+Buffering&amp;rft.date=2006&amp;rft.aulast=Graham&amp;rft.aufirst=Timur&amp;rft_id=http%3A%2F%2Ffitsweb.uchc.edu%2Fstudent%2Fselectives%2FTimurGraham%2FAcid_Buffering.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> <li id="cite_note-Voet_acid_cat-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-Voet_acid_cat_24-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVoet,_Judith_G.Voet,_Donald2004" class="citation book cs1">Voet, Judith G.; Voet, Donald (2004). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/biochemistry00voet_1"><i>Biochemistry</i></a></span>. New York: J. Wiley &amp; Sons. pp.&#160;<a rel="nofollow" class="external text" href="https://archive.org/details/biochemistry00voet_1/page/496">496–500</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-471-19350-0" title="Special:BookSources/978-0-471-19350-0"><bdi>978-0-471-19350-0</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=Biochemistry&amp;rft.place=New+York&amp;rft.pages=496-500&amp;rft.pub=J.+Wiley+%26+Sons&amp;rft.date=2004&amp;rft.isbn=978-0-471-19350-0&amp;rft.au=Voet%2C+Judith+G.&amp;rft.au=Voet%2C+Donald&amp;rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fbiochemistry00voet_1&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></span> </li> </ol></div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20011218075412/http://www.csudh.edu/oliver/chemdata/data-ka.htm">Listing of strengths of common acids and bases</a></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZumdahl1997" class="citation book cs1">Zumdahl, Steven S. (1997). <i>Chemistry</i> (4th&#160;ed.). Boston: Houghton Mifflin. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9780669417944" title="Special:BookSources/9780669417944"><bdi>9780669417944</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=Chemistry&amp;rft.place=Boston&amp;rft.edition=4th&amp;rft.pub=Houghton+Mifflin&amp;rft.date=1997&amp;rft.isbn=9780669417944&amp;rft.aulast=Zumdahl&amp;rft.aufirst=Steven+S.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPaviaLampmanKriz2004" class="citation book cs1">Pavia, D. L.; Lampman, G. M.; Kriz, G. S. (2004). <i>Organic Chemistry Volume I</i>. Mason, OH: Cengage Learning. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/0759347271" title="Special:BookSources/0759347271"><bdi>0759347271</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=Organic+Chemistry+Volume+I&amp;rft.place=Mason%2C+OH&amp;rft.pub=Cengage+Learning&amp;rft.date=2004&amp;rft.isbn=0759347271&amp;rft.aulast=Pavia&amp;rft.aufirst=D.+L.&amp;rft.au=Lampman%2C+G.+M.&amp;rft.au=Kriz%2C+G.+S.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2></div> <ul><li><a rel="nofollow" class="external text" href="http://www2.iq.usp.br/docente/gutz/Curtipot_.html">Curtipot</a>: Acid–Base equilibria diagrams, <a href="/wiki/PH" title="PH">pH</a> calculation and <a href="/wiki/Titration" title="Titration">titration</a> curves simulation and analysis – <a href="/wiki/Freeware" title="Freeware">freeware</a></li></ul> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output 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