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class="vector-toc-numb">2</span> <span>Lewis acids</span> </div> </a> <button aria-controls="toc-Lewis_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 Lewis acids subsection</span> </button> <ul id="toc-Lewis_acids-sublist" class="vector-toc-list"> <li id="toc-Simple_Lewis_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Simple_Lewis_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Simple Lewis acids</span> </div> </a> <ul id="toc-Simple_Lewis_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Complex_Lewis_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Complex_Lewis_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Complex Lewis acids</span> </div> </a> <ul id="toc-Complex_Lewis_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-H+_as_Lewis_acid" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#H+_as_Lewis_acid"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>H<sup>+</sup> as Lewis acid</span> </div> </a> <ul id="toc-H+_as_Lewis_acid-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Applications_of_Lewis_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Applications_of_Lewis_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Applications of Lewis acids</span> </div> </a> <ul id="toc-Applications_of_Lewis_acids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Lewis_bases" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Lewis_bases"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Lewis bases</span> </div> </a> <button aria-controls="toc-Lewis_bases-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 Lewis bases subsection</span> </button> <ul id="toc-Lewis_bases-sublist" class="vector-toc-list"> <li id="toc-Applications_of_Lewis_bases" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Applications_of_Lewis_bases"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Applications of Lewis bases</span> </div> </a> <ul id="toc-Applications_of_Lewis_bases-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Hard_and_soft_classification" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Hard_and_soft_classification"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Hard and soft classification</span> </div> </a> <ul id="toc-Hard_and_soft_classification-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Quantifying_Lewis_acidity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Quantifying_Lewis_acidity"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Quantifying Lewis acidity</span> </div> </a> <ul id="toc-Quantifying_Lewis_acidity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>History</span> </div> </a> <button aria-controls="toc-History-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 History subsection</span> </button> <ul id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Reformulation_of_Lewis_theory" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reformulation_of_Lewis_theory"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Reformulation of Lewis theory</span> </div> </a> <ul id="toc-Reformulation_of_Lewis_theory-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Comparison_with_Brønsted–Lowry_theory" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Comparison_with_Brønsted–Lowry_theory"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Comparison with Brønsted–Lowry theory</span> </div> </a> <ul id="toc-Comparison_with_Brønsted–Lowry_theory-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-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">Lewis acids and bases</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 31 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-31" 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">31 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Lewis-suur_en_-basis" title="Lewis-suur en -basis – Afrikaans" lang="af" hreflang="af" data-title="Lewis-suur en -basis" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D8%AD%D9%85%D8%A7%D8%B6_%D9%88%D9%82%D9%88%D8%A7%D8%B9%D8%AF_%D9%84%D9%88%D9%8A%D8%B3" title="أحماض وقواعد لويس – Arabic" lang="ar" hreflang="ar" data-title="أحماض وقواعد لويس" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B2%E0%A7%81%E0%A6%87%E0%A6%B8_%E0%A6%85%E0%A6%AE%E0%A7%8D%E0%A6%B2_%E0%A6%93_%E0%A6%95%E0%A7%8D%E0%A6%B7%E0%A6%BE%E0%A6%B0" title="লুইস অম্ল ও ক্ষার – Bangla" lang="bn" hreflang="bn" data-title="লুইস অম্ল ও ক্ষার" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Lewisova_kiselina_i_baza" title="Lewisova kiselina i baza – Bosnian" lang="bs" hreflang="bs" data-title="Lewisova kiselina i baza" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Teoria_%C3%A0cid-base_de_Lewis" title="Teoria àcid-base de Lewis – Catalan" lang="ca" hreflang="ca" data-title="Teoria àcid-base de Lewis" 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/Lewisova_teorie_kyselin_a_z%C3%A1sad" title="Lewisova teorie kyselin a zásad – Czech" lang="cs" hreflang="cs" data-title="Lewisova teorie kyselin a zásad" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Lewis-S%C3%A4ure-Base-Konzept" title="Lewis-Säure-Base-Konzept – German" lang="de" hreflang="de" data-title="Lewis-Säure-Base-Konzept" 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/Lewisi_happed_ja_alused" title="Lewisi happed ja alused – Estonian" lang="et" hreflang="et" data-title="Lewisi happed ja alused" 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%CE%AD%CE%B1_%CE%BA%CE%B1%CE%B9_%CE%B2%CE%AC%CF%83%CE%B5%CE%B9%CF%82_%CE%BA%CE%B1%CF%84%CE%AC_%CE%9B%CE%B9%CE%BF%CF%8D%CE%B9%CF%82" title="Οξέα και βάσεις κατά Λιούις – Greek" lang="el" hreflang="el" data-title="Οξέα και βάσεις κατά Λιούις" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Teor%C3%ADa_%C3%A1cido-base_de_Lewis" title="Teoría ácido-base de Lewis – Spanish" lang="es" hreflang="es" data-title="Teoría ácido-base de Lewis" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Lewisen_azido_eta_baseak" title="Lewisen azido eta baseak – Basque" lang="eu" hreflang="eu" data-title="Lewisen azido eta baseak" 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_%D9%88_%D8%A8%D8%A7%D8%B2_%D9%84%D9%88%DB%8C%DB%8C%D8%B3" title="اسید و باز لوییس – Persian" lang="fa" hreflang="fa" data-title="اسید و باز لوییس" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Acides_et_bases_de_Lewis" title="Acides et bases de Lewis – French" lang="fr" hreflang="fr" data-title="Acides et bases de Lewis" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B2%E0%A5%81%E0%A4%88%E0%A4%B8_%E0%A4%95%E0%A5%87_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2_%E0%A4%94%E0%A4%B0_%E0%A4%95%E0%A5%8D%E0%A4%B7%E0%A4%BE%E0%A4%B0" title="लुईस के अम्ल और क्षार – Hindi" lang="hi" hreflang="hi" data-title="लुईस के अम्ल और क्षार" 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/Lewisove_kiseline_i_baze" title="Lewisove kiseline i baze – Croatian" lang="hr" hreflang="hr" data-title="Lewisove kiseline i baze" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_dan_basa_Lewis" title="Asam dan basa Lewis – Indonesian" lang="id" hreflang="id" data-title="Asam dan basa Lewis" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Teoria_acido-base_di_Lewis" title="Teoria acido-base di Lewis – Italian" lang="it" hreflang="it" data-title="Teoria acido-base di Lewis" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/L%C5%ABisa_sk%C4%81bes_un_b%C4%81zes" title="Lūisa skābes un bāzes – Latvian" lang="lv" hreflang="lv" data-title="Lūisa skābes un bāzes" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B2%E0%B5%82%E0%B4%AF%E0%B4%BF%E0%B4%B8%E0%B5%8D_%E0%B4%85%E0%B4%AE%E0%B5%8D%E0%B4%B2%E0%B4%99%E0%B5%8D%E0%B4%99%E0%B4%B3%E0%B5%81%E0%B4%82_%E0%B4%B2%E0%B5%82%E0%B4%AF%E0%B4%BF%E0%B4%B8%E0%B5%8D_%E0%B4%95%E0%B5%8D%E0%B4%B7%E0%B4%BE%E0%B4%B0%E0%B4%99%E0%B5%8D%E0%B4%99%E0%B4%B3%E0%B5%81%E0%B4%82" title="ലൂയിസ് അമ്ലങ്ങളും ലൂയിസ് ക്ഷാരങ്ങളും – Malayalam" lang="ml" hreflang="ml" data-title="ലൂയിസ് അമ്ലങ്ങളും ലൂയിസ് ക്ഷാരങ്ങളും" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%AB%E3%82%A4%E3%82%B9%E3%81%AE%E7%90%86%E8%AB%96" title="ルイスの理論 – Japanese" lang="ja" hreflang="ja" data-title="ルイスの理論" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Lewis_syrer_og_baser" title="Lewis syrer og baser – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Lewis syrer og baser" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Teoria_kwas%C3%B3w_i_zasad_Lewisa" title="Teoria kwasów i zasad Lewisa – Polish" lang="pl" hreflang="pl" data-title="Teoria kwasów i zasad Lewisa" 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/Teoria_%C3%A1cido-base_de_Lewis" title="Teoria ácido-base de Lewis – Portuguese" lang="pt" hreflang="pt" data-title="Teoria ácido-base de Lewis" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Lewisova_teorija_kislin_in_baz" title="Lewisova teorija kislin in baz – Slovenian" lang="sl" hreflang="sl" data-title="Lewisova teorija kislin in baz" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Luisove_kiseline_i_baze" title="Luisove kiseline i baze – Serbian" lang="sr" hreflang="sr" data-title="Luisove kiseline i baze" 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/Lewisove_kiseline_i_baze" title="Lewisove kiseline i baze – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Lewisove kiseline i baze" 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-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%B2%E0%AF%82%E0%AE%AF%E0%AE%BF%E0%AE%9A%E0%AF%81_%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2%E0%AE%99%E0%AF%8D%E0%AE%95%E0%AE%B3%E0%AF%81%E0%AE%AE%E0%AF%8D_%E0%AE%95%E0%AE%BE%E0%AE%B0%E0%AE%99%E0%AF%8D%E0%AE%95%E0%AE%B3%E0%AF%81%E0%AE%AE%E0%AF%8D" title="லூயிசு அமிலங்களும் காரங்களும் – Tamil" lang="ta" hreflang="ta" data-title="லூயிசு அமிலங்களும் காரங்களும்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Lewis_asit_ve_baz%C4%B1" title="Lewis asit ve bazı – Turkish" lang="tr" hreflang="tr" data-title="Lewis asit ve bazı" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D9%84%DB%8C%D9%88%D8%B3_%D8%AA%DB%8C%D8%B2%D8%A7%D8%A8_%D8%A7%D9%88%D8%B1_%D8%A7%D8%B3%D8%A7%D8%B3" title="لیوس تیزاب اور اساس – Urdu" lang="ur" hreflang="ur" data-title="لیوس تیزاب اور اساس" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Acid_v%C3%A0_base_Lewis" title="Acid và base Lewis – Vietnamese" lang="vi" hreflang="vi" data-title="Acid và base Lewis" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link 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<div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical bond theory</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Lewis_bases_and_acids.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Lewis_bases_and_acids.jpg/400px-Lewis_bases_and_acids.jpg" decoding="async" width="400" height="190" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Lewis_bases_and_acids.jpg/600px-Lewis_bases_and_acids.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/2/22/Lewis_bases_and_acids.jpg 2x" data-file-width="723" data-file-height="343" /></a><figcaption>Diagram of some Lewis <span style="color:blue;">bases (left)</span> and <span style="color:red;">acids (right)</span></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 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.sidebar{display:table!important;float:right!important;margin:0.5em 0 1em 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 href="/wiki/Acid" title="Acid">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 href="/wiki/Acid" title="Acid">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 class="mw-selflink selflink">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 class="mw-selflink selflink">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>A <b>Lewis acid</b> (named for the American physical chemist <a href="/wiki/Gilbert_N._Lewis" title="Gilbert N. Lewis">Gilbert N. Lewis</a>) is a chemical species that contains an empty <a href="/wiki/Non-bonding_orbital" title="Non-bonding orbital">orbital</a> which is capable of accepting an <a href="/wiki/Electron_pair" title="Electron pair">electron pair</a> from a Lewis <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a> to form a Lewis <a href="/wiki/Adduct" title="Adduct">adduct</a>. A <b>Lewis base</b>, then, is any species that has a filled orbital containing an electron pair which is not involved in <a href="/wiki/Covalent_bond" title="Covalent bond">bonding</a> but may form a <a href="/wiki/Dative_bond" class="mw-redirect" title="Dative bond">dative bond</a> with a Lewis acid to form a Lewis adduct. For example, <a href="/wiki/Ammonia" title="Ammonia">NH<sub>3</sub></a> is a Lewis base, because it can donate its <a href="/wiki/Lone_pair" title="Lone pair">lone pair</a> of electrons. <a href="/wiki/Trimethylborane" title="Trimethylborane">Trimethylborane</a> [(CH<sub>3</sub>)<sub>3</sub>B] is a Lewis acid as it is capable of accepting a lone pair. In a Lewis adduct, the Lewis acid and base share an electron pair furnished by the Lewis base, forming a dative bond.<sup id="cite_ref-Gold_Book_Lewis_acid_L03508_1-0" class="reference"><a href="#cite_note-Gold_Book_Lewis_acid_L03508-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> In the context of a specific <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reaction</a> between NH<sub>3</sub> and Me<sub>3</sub>B, a lone pair from NH<sub>3</sub> will form a dative bond with the empty orbital of Me<sub>3</sub>B to form an adduct NH<sub>3</sub>•BMe<sub>3</sub>. The terminology refers to the contributions of <a href="/wiki/Gilbert_N._Lewis" title="Gilbert N. Lewis">Gilbert N. Lewis</a>.<sup id="cite_ref-lewisvalence_2-0" class="reference"><a href="#cite_note-lewisvalence-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>The terms <i><a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a></i> and <i><a href="/wiki/Electrophile" title="Electrophile">electrophile</a></i> are sometimes interchangeable with Lewis base and Lewis acid, respectively. These terms, especially their abstract noun forms <i>nucleophilicity</i> and <i>electrophilicity</i>, emphasize the <a href="/wiki/Kinetic_energy" title="Kinetic energy">kinetic</a> aspect of reactivity, while the Lewis basicity and Lewis acidity emphasize the <a href="/wiki/Thermodynamics" title="Thermodynamics">thermodynamic</a> aspect of Lewis adduct formation.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Depicting_adducts">Depicting adducts</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=1" title="Edit section: Depicting adducts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In many cases, the interaction between the Lewis base and Lewis acid in a complex is indicated by an arrow indicating the Lewis base donating electrons toward the Lewis acid using the notation of a <a href="/wiki/Dative_bond" class="mw-redirect" title="Dative bond">dative bond</a> — for example, <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">Me<sub class="template-chem2-sub">3</sub>B</span>←<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NH<sub class="template-chem2-sub">3</sub></span>. Some sources indicate the Lewis base with a pair of dots (the explicit electrons being donated), which allows consistent representation of the transition from the base itself to the complex with the acid: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Me<sub class="template-chem2-sub">3</sub>B + :NH<sub class="template-chem2-sub">3</sub> → Me<sub class="template-chem2-sub">3</sub>B:NH<sub class="template-chem2-sub">3</sub></span></dd></dl> <p>A center dot may also be used to represent a Lewis adduct, such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Me<sub class="template-chem2-sub">3</sub>B·NH<sub class="template-chem2-sub">3</sub></span>. Another example is <a href="/wiki/Boron_trifluoride_diethyl_etherate" class="mw-redirect" title="Boron trifluoride diethyl etherate">boron trifluoride diethyl etherate</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">BF<sub class="template-chem2-sub">3</sub>·Et<sub class="template-chem2-sub">2</sub>O</span>. In a slightly different usage, the center dot is also used to represent <a href="/wiki/Water_of_crystallization" title="Water of crystallization">hydrate coordination</a> in various crystals, as in <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">MgSO<sub class="template-chem2-sub">4</sub>·7H<sub>2</sub>O</span> for hydrated <a href="/wiki/Magnesium_sulfate" title="Magnesium sulfate">magnesium sulfate</a>, irrespective of whether the water forms a dative bond with the metal. </p><p>Although there have been attempts to use computational and experimental energetic criteria to distinguish dative bonding from non-dative covalent bonds,<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> for the most part, the distinction merely makes note of the source of the electron pair, and dative bonds, once formed, behave simply as other covalent bonds do, though they typically have considerable polar character. Moreover, in some cases (e.g., sulfoxides and amine oxides as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">2</sub>S → O</span> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">3</sub>N → O</span>), the use of the dative bond arrow is just a notational convenience for avoiding the drawing of formal charges. In general, however, the donor–acceptor bond is viewed as simply somewhere along a continuum between idealized <a href="/wiki/Covalent_bonding" class="mw-redirect" title="Covalent bonding">covalent bonding</a> and <a href="/wiki/Ionic_bonding" title="Ionic bonding">ionic bonding</a>.<sup id="cite_ref-March_5-0" class="reference"><a href="#cite_note-March-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Lewis_acids">Lewis acids</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=2" title="Edit section: Lewis acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:NH3-BF3-adduct-bond-lengthening-2D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/NH3-BF3-adduct-bond-lengthening-2D.png/270px-NH3-BF3-adduct-bond-lengthening-2D.png" decoding="async" width="270" height="127" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/NH3-BF3-adduct-bond-lengthening-2D.png/405px-NH3-BF3-adduct-bond-lengthening-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/NH3-BF3-adduct-bond-lengthening-2D.png/540px-NH3-BF3-adduct-bond-lengthening-2D.png 2x" data-file-width="1100" data-file-height="516" /></a><figcaption>Major structural changes accompany binding of the Lewis base to the coordinatively unsaturated, planar Lewis acid BF<sub>3</sub></figcaption></figure> <p>Lewis acids are diverse and the term is used loosely. Simplest are those that react directly with the Lewis base, such as boron trihalides and the pentahalides of phosphorus, arsenic, and antimony. </p><p>In the same vein, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<span class="template-chem2-su"><span>+</span><span>3</span></span></span> can be considered to be the Lewis acid in methylation reactions. However, the methyl cation never occurs as a free species in the condensed phase, and methylation reactions by reagents like CH<sub>3</sub>I take place through the simultaneous formation of a bond from the nucleophile to the carbon and cleavage of the bond between carbon and iodine (S<sub>N</sub>2 reaction). Textbooks disagree on this point: some asserting that alkyl halides are electrophiles but not Lewis acids,<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> while others describe alkyl halides (e.g. CH<sub>3</sub>Br) as a type of Lewis acid.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/IUPAC_Gold_Book" class="mw-redirect" title="IUPAC Gold Book">IUPAC</a> states that Lewis acids and Lewis bases react to form Lewis adducts,<sup id="cite_ref-Gold_Book_Lewis_acid_L03508_1-1" class="reference"><a href="#cite_note-Gold_Book_Lewis_acid_L03508-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> and defines electrophile as Lewis acids.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Simple_Lewis_acids">Simple Lewis acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=3" title="Edit section: Simple Lewis acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some of the most studied examples of such Lewis acids are the boron trihalides and <a href="/wiki/Organoboranes" class="mw-redirect" title="Organoboranes">organoboranes</a>:<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>BF<sub>3</sub> + F<sup>−</sup> → <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">BF<span class="template-chem2-su"><span>−</span><span>4</span></span></span></dd></dl> <p>In this adduct, all four fluoride centres (or more accurately, <a href="/wiki/Ligand" title="Ligand">ligands</a>) are equivalent. </p> <dl><dd>BF<sub>3</sub> + OMe<sub>2</sub> → BF<sub>3</sub>OMe<sub>2</sub></dd></dl> <p>Both BF<sub>4</sub><sup>−</sup> and BF<sub>3</sub>OMe<sub>2</sub> are Lewis base adducts of boron trifluoride. </p><p>Many adducts violate the <a href="/wiki/Octet_rule" title="Octet rule">octet rule</a>, such as the <a href="/wiki/Triiodide" title="Triiodide">triiodide</a> anion: </p> <dl><dd>I<sub>2</sub> + I<sup>−</sup> → <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">I<span class="template-chem2-su"><span>−</span><span>3</span></span></span></dd></dl> <p>The variability of the colors of iodine solutions reflects the variable abilities of the solvent to form adducts with the Lewis acid I<sub>2</sub>. </p><p>Some Lewis acids bind with two Lewis bases, a famous example being the formation of <a href="/wiki/Hexafluorosilicate" class="mw-redirect" title="Hexafluorosilicate">hexafluorosilicate</a>: </p> <dl><dd>SiF<sub>4</sub> + 2 F<sup>−</sup> → <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">SiF<span class="template-chem2-su"><span>2−</span><span>6</span></span></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Complex_Lewis_acids">Complex Lewis acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=4" title="Edit section: Complex Lewis acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most compounds considered to be Lewis acids require an activation step prior to formation of the adduct with the Lewis base. Complex compounds such as <a href="/wiki/Ethylaluminium_sesquichloride" title="Ethylaluminium sesquichloride">Et<sub>3</sub>Al<sub>2</sub>Cl<sub>3</sub></a> and <a href="/wiki/Aluminium_chloride" title="Aluminium chloride">AlCl<sub>3</sub></a> are treated as trigonal planar Lewis acids but exist as aggregates and polymers that must be degraded by the Lewis base.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> A simpler case is the formation of adducts of borane. Monomeric BH<sub>3</sub> does not exist appreciably, so the adducts of borane are generated by degradation of diborane: </p> <dl><dd>B<sub>2</sub>H<sub>6</sub> + 2 H<sup>−</sup> → 2 <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">BH<span class="template-chem2-su"><span>−</span><span>4</span></span></span></dd></dl> <p>In this case, an intermediate <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">B<sub class="template-chem2-sub">2</sub>H<span class="template-chem2-su"><span>−</span><span>7</span></span></span> can be isolated. </p><p>Many metal complexes serve as Lewis acids, but usually only after dissociating a more weakly bound Lewis base, often water. </p> <dl><dd>[Mg(H<sub>2</sub>O)<sub>6</sub>]<sup>2+</sup> + 6 NH<sub>3</sub> → [Mg(NH<sub>3</sub>)<sub>6</sub>]<sup>2+</sup> + 6 H<sub>2</sub>O</dd></dl> <div class="mw-heading mw-heading3"><h3 id="H+_as_Lewis_acid"><span id="H.2B_as_Lewis_acid"></span>H<sup>+</sup> as Lewis acid</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=5" title="Edit section: H+ as Lewis acid"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Proton" title="Proton">proton</a> (H<sup>+</sup>) <sup id="cite_ref-hydron_11-0" class="reference"><a href="#cite_note-hydron-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> is one of the strongest but is also one of the most complicated Lewis acids. It is convention to ignore the fact that a proton is heavily solvated (bound to solvent). With this simplification in mind, acid-base reactions can be viewed as the formation of adducts: </p> <ul><li>H<sup>+</sup> + NH<sub>3</sub> → <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NH<span class="template-chem2-su"><span>+</span><span>4</span></span></span></li> <li>H<sup>+</sup> + OH<sup>−</sup> → H<sub>2</sub>O</li></ul> <div class="mw-heading mw-heading3"><h3 id="Applications_of_Lewis_acids">Applications of Lewis acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=6" title="Edit section: Applications of Lewis acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A typical example of a Lewis acid in action is in the <a href="/wiki/Friedel%E2%80%93Crafts_alkylation" class="mw-redirect" title="Friedel–Crafts alkylation">Friedel–Crafts alkylation</a> reaction.<sup id="cite_ref-March_5-1" class="reference"><a href="#cite_note-March-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The key step is the acceptance by AlCl<sub>3</sub> of a chloride ion lone-pair, forming <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">AlCl<span class="template-chem2-su"><span>−</span><span>4</span></span></span> and creating the strongly acidic, that is, <a href="/wiki/Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a>, carbonium ion. </p> <dl><dd>RCl +AlCl<sub>3</sub> → R<sup>+</sup> + <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">AlCl<span class="template-chem2-su"><span>−</span><span>4</span></span></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Lewis_bases">Lewis bases</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=7" title="Edit section: Lewis bases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A Lewis base is an atomic or molecular species where the <a href="/wiki/HOMO" class="mw-redirect" title="HOMO">highest occupied molecular orbital</a> (HOMO) is highly localized. Typical Lewis bases are conventional <a href="/wiki/Amine" title="Amine">amines</a> such as ammonia and <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> amines. Other common Lewis bases include <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> and its derivatives. Some of the main classes of Lewis bases are </p> <ul><li>amines of the formula NH<sub>3−<var>x</var></sub>R<sub><var>x</var></sub> where R = alkyl or <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a>. Related to these are pyridine and its derivatives.</li> <li><a href="/wiki/Phosphine" title="Phosphine">phosphines</a> of the formula PR<sub>3−<var>x</var></sub>Ar<sub><var>x</var></sub>.</li> <li>compounds of O, S, Se and Te in oxidation state −2, including water, <a href="/wiki/Ether" title="Ether">ethers</a>, <a href="/wiki/Ketone" title="Ketone">ketones</a></li></ul> <p>The most common Lewis bases are anions. The strength of Lewis basicity correlates with the <var style="padding-right: 1px;">pK<sub>a</sub></var> of the parent acid: acids with high <var style="padding-right: 1px;">pK<sub>a</sub></var>'s give good Lewis bases. As usual, a <a href="/wiki/Acid_strength" title="Acid strength">weaker acid</a> has a stronger <a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">conjugate base</a>. </p> <ul><li>Examples of Lewis bases based on the general definition of electron pair donor include: <ul><li>simple anions, such as <a href="/wiki/Hydride" title="Hydride">H<sup>−</sup></a> and <a href="/wiki/Fluoride" title="Fluoride">F<sup>−</sup></a></li> <li>other lone-pair-containing species, such as H<sub>2</sub>O, NH<sub>3</sub>, <a href="/wiki/Hydroxide" title="Hydroxide">HO<sup>−</sup></a>, and CH<sub>3</sub><sup>−</sup></li> <li>complex anions, such as <a href="/wiki/Sulfate" title="Sulfate">sulfate</a></li> <li>electron-rich <span class="texhtml mvar" style="font-style:italic;">π</span>-system Lewis bases, such as <a href="/wiki/Ethyne" class="mw-redirect" title="Ethyne">ethyne</a>, <a href="/wiki/Ethene" class="mw-redirect" title="Ethene">ethene</a>, and <a href="/wiki/Benzene" title="Benzene">benzene</a></li></ul></li></ul> <p>The strength of Lewis bases have been evaluated for various Lewis acids, such as I<sub>2</sub>, SbCl<sub>5</sub>, and BF<sub>3</sub>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable collapsible" align="center" border="1" cellspacing="0" cellpadding="0" style="margin: 0 0 0 0em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C030;"> <caption style="background:#ffdead;">Heats of binding of various bases to <a href="/wiki/Boron_trifluoride" title="Boron trifluoride">BF<sub>3</sub></a> </caption> <tbody><tr> <th style="background:#ffdead;">Lewis base </th> <th style="background:#ffdead;">Donor atom </th> <th style="background:#ffdead;">Enthalpy of complexation (kJ/mol) </th></tr> <tr> <td><a href="/wiki/Quinuclidine" title="Quinuclidine">Quinuclidine</a> </td> <td>N </td> <td>150 </td></tr> <tr> <td><a href="/wiki/Triethylamine" title="Triethylamine">Et<sub>3</sub>N</a> </td> <td>N </td> <td>135 </td></tr> <tr> <td><a href="/wiki/Pyridine" title="Pyridine">Pyridine</a> </td> <td>N </td> <td>128 </td></tr> <tr> <td><a href="/wiki/Acetonitrile" title="Acetonitrile">Acetonitrile</a> </td> <td>N </td> <td>60 </td></tr> <tr> <td><a href="/wiki/Dimethylacetamide" title="Dimethylacetamide">DMA</a> </td> <td>O </td> <td>112 </td></tr> <tr> <td><a href="/wiki/Dimethyl_sulfoxide" title="Dimethyl sulfoxide">DMSO</a> </td> <td>O </td> <td>105 </td></tr> <tr> <td><a href="/wiki/THF" class="mw-redirect" title="THF">THF</a> </td> <td>O </td> <td>90.4 </td></tr> <tr> <td><a href="/wiki/Diethylether" class="mw-redirect" title="Diethylether">Et<sub>2</sub>O</a> </td> <td>O </td> <td>78.8 </td></tr> <tr> <td><a href="/wiki/Acetone" title="Acetone">Acetone</a> </td> <td>O </td> <td>76.0 </td></tr> <tr> <td><a href="/wiki/Ethylacetate" class="mw-redirect" title="Ethylacetate">EtOAc</a> </td> <td>O </td> <td>75.5 </td></tr> <tr> <td><a href="/wiki/Trimethylphosphine" title="Trimethylphosphine">Trimethylphosphine</a> </td> <td>P </td> <td>97.3 </td></tr> <tr> <td><a href="/wiki/Tetrahydrothiophene" title="Tetrahydrothiophene">Tetrahydrothiophene</a> </td> <td>S </td> <td>51.6 </td></tr> </tbody></table> <div class="mw-heading mw-heading3"><h3 id="Applications_of_Lewis_bases">Applications of Lewis bases</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=8" title="Edit section: Applications of Lewis bases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Homogeneous_catalysis" title="Homogeneous catalysis">Homogeneous catalysis</a></div> <p>Nearly all electron pair donors that form compounds by binding transition elements can be viewed <a href="/wiki/Ligand" title="Ligand">ligands</a>. Thus, a large application of Lewis bases is to modify the activity and selectivity of <a href="/wiki/Homogeneous_catalysis" title="Homogeneous catalysis">metal catalysts</a>. Chiral Lewis bases, generally <a href="/wiki/Multidentate" class="mw-redirect" title="Multidentate">multidentate</a>, confer <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chirality</a> on a catalyst, enabling <a href="/wiki/Asymmetric_catalysis" class="mw-redirect" title="Asymmetric catalysis">asymmetric catalysis</a>, which is useful for the production of <a href="/wiki/Pharmaceutical" class="mw-redirect" title="Pharmaceutical">pharmaceuticals</a>. The industrial synthesis of the anti-hypertension drug <a href="/wiki/Mibefradil" title="Mibefradil">mibefradil</a> uses a chiral Lewis base (<i>R</i>-MeOBIPHEP), for example.<sup id="cite_ref-CompAsymmetricCatalysis_13-0" class="reference"><a href="#cite_note-CompAsymmetricCatalysis-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Partial_Roche_Synthesis_of_Mibefradil.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Partial_Roche_Synthesis_of_Mibefradil.tif/lossless-page1-700px-Partial_Roche_Synthesis_of_Mibefradil.tif.png" decoding="async" width="700" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Partial_Roche_Synthesis_of_Mibefradil.tif/lossless-page1-1050px-Partial_Roche_Synthesis_of_Mibefradil.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Partial_Roche_Synthesis_of_Mibefradil.tif/lossless-page1-1400px-Partial_Roche_Synthesis_of_Mibefradil.tif.png 2x" data-file-width="2591" data-file-height="370" /></a><figcaption></figcaption></figure> <p><br /> </p> <div class="mw-heading mw-heading2"><h2 id="Hard_and_soft_classification">Hard and soft classification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=9" title="Edit section: Hard and soft classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/HSAB_theory" title="HSAB theory">HSAB theory</a></div> <p>Lewis acids and bases are commonly classified according to their hardness or softness. In this context hard implies small and nonpolarizable and soft indicates larger atoms that are more polarizable. </p> <ul><li>typical hard acids: H<sup>+</sup>, alkali/alkaline earth metal cations, boranes, Zn<sup>2+</sup></li> <li>typical soft acids: Ag<sup>+</sup>, Mo(0), Ni(0), Pt<sup>2+</sup></li> <li>typical hard bases: ammonia and amines, water, carboxylates, fluoride and chloride</li> <li>typical soft bases: organophosphines, thioethers, carbon monoxide, iodide</li></ul> <p>For example, an <a href="/wiki/Amine" title="Amine">amine</a> will displace <a href="/wiki/Phosphine" title="Phosphine">phosphine</a> from the adduct with the acid BF<sub>3</sub>. In the same way, bases could be classified. For example, bases donating a lone pair from an oxygen atom are harder than bases donating through a nitrogen atom. Although the classification was never quantified it proved to be very useful in predicting the strength of adduct formation, using the key concepts that hard acid—hard base and soft acid—soft base interactions are stronger than hard acid—soft base or soft acid—hard base interactions. Later investigation of the thermodynamics of the interaction suggested that hard—hard interactions are <a href="/wiki/Enthalpy" title="Enthalpy">enthalpy</a> favored, whereas soft—soft are <a href="/wiki/Entropy" title="Entropy">entropy</a> favored.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Quantifying_Lewis_acidity">Quantifying Lewis acidity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=10" title="Edit section: Quantifying Lewis acidity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many methods have been devised to evaluate and predict Lewis acidity. Many are based on spectroscopic signatures such as shifts NMR signals or IR bands e.g. the <a href="/wiki/Gutmann-Beckett_method" class="mw-redirect" title="Gutmann-Beckett method">Gutmann-Beckett method</a> and the Childs<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> method. </p><p>The <a href="/wiki/ECW_model" title="ECW model">ECW model</a> is a quantitative model that describes and predicts the strength of Lewis acid base interactions, −ΔH. The model assigned E and C parameters to many Lewis acids and bases. Each acid is characterized by an E<sub>A</sub> and a C<sub>A</sub>. Each base is likewise characterized by its own E<sub>B</sub> and C<sub>B</sub>. The E and C parameters refer, respectively, to the electrostatic and covalent contributions to the strength of the bonds that the acid and base will form. The equation is </p> <dl><dd>−ΔH = E<sub>A</sub>E<sub>B</sub> + C<sub>A</sub>C<sub>B</sub> + W</dd></dl> <p>The W term represents a constant energy contribution for acid–base reaction such as the cleavage of a dimeric acid or base. The equation predicts reversal of acids and base strengths. The graphical presentations of the equation show that there is no single order of Lewis base strengths or Lewis acid strengths.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> and that single property scales are limited to a smaller range of acids or bases. </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=11" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Dative_covalent_bond2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Dative_covalent_bond2.png/220px-Dative_covalent_bond2.png" decoding="async" width="220" height="195" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Dative_covalent_bond2.png/330px-Dative_covalent_bond2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/62/Dative_covalent_bond2.png/440px-Dative_covalent_bond2.png 2x" data-file-width="480" data-file-height="426" /></a><figcaption><a href="/wiki/MO_diagram" class="mw-redirect" title="MO diagram">MO diagram</a> depicting the formation of a dative covalent bond between two atoms</figcaption></figure> <p>The concept originated with <a href="/wiki/Gilbert_N._Lewis" title="Gilbert N. Lewis">Gilbert N. Lewis</a> who studied <a href="/wiki/Chemical_bonding" class="mw-redirect" title="Chemical bonding">chemical bonding</a>. In 1923, Lewis wrote <i>An acid substance is one which can employ an electron lone pair from another molecule in completing the stable group of one of its own atoms.</i><sup id="cite_ref-lewisvalence_2-1" class="reference"><a href="#cite_note-lewisvalence-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-lewis_1_17-0" class="reference"><a href="#cite_note-lewis_1-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The <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> was published in the same year. The two theories are distinct but complementary. A Lewis base is also a Brønsted–Lowry base, but a Lewis acid does not need to be a Brønsted–Lowry acid. The classification into hard and soft acids and bases (<a href="/wiki/HSAB_theory" title="HSAB theory">HSAB theory</a>) followed in 1963. The strength of Lewis acid-base interactions, as measured by the standard <a href="/wiki/Enthalpy" title="Enthalpy">enthalpy</a> of formation of an adduct can be predicted by the Drago–Wayland two-parameter equation. </p> <div class="mw-heading mw-heading3"><h3 id="Reformulation_of_Lewis_theory">Reformulation of Lewis theory</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=12" title="Edit section: Reformulation of Lewis theory"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lewis had suggested in 1916 that two <a href="/wiki/Atom" title="Atom">atoms</a> are held together in a chemical bond by sharing a pair of electrons.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> When each atom contributed one electron to the bond, it was called a <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bond</a>. When both electrons come from one of the atoms, it was called a dative covalent bond or <a href="/wiki/Coordinate_bond" class="mw-redirect" title="Coordinate bond">coordinate bond</a>. The distinction is not very clear-cut. For example, in the formation of an ammonium ion from ammonia and hydrogen the <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> molecule donates a pair of electrons to the <a href="/wiki/Hydron_(chemistry)" title="Hydron (chemistry)">proton</a>;<sup id="cite_ref-hydron_11-1" class="reference"><a href="#cite_note-hydron-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> the identity of the electrons is lost in the <a href="/wiki/Ammonium" title="Ammonium">ammonium</a> ion that is formed. Nevertheless, Lewis suggested that an electron-pair donor be classified as a base and an electron-pair acceptor be classified as acid. </p><p>A more modern definition of a Lewis acid is an atomic or molecular species with a localized empty <a href="/wiki/Atomic_orbital" title="Atomic orbital">atomic</a> or <a href="/wiki/Molecular_orbital" title="Molecular orbital">molecular</a> orbital of low energy. This lowest-energy molecular orbital (<a href="/wiki/LUMO" class="mw-redirect" title="LUMO">LUMO</a>) can accommodate a pair of electrons. </p> <div class="mw-heading mw-heading3"><h3 id="Comparison_with_Brønsted–Lowry_theory"><span id="Comparison_with_Br.C3.B8nsted.E2.80.93Lowry_theory"></span>Comparison with Brønsted–Lowry theory</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=13" title="Edit section: Comparison with Brønsted–Lowry theory"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A Lewis base is often a Brønsted–Lowry base as it can donate a pair of electrons to H<sup>+</sup>;<sup id="cite_ref-hydron_11-2" class="reference"><a href="#cite_note-hydron-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> the proton is a Lewis acid as it can accept a pair of electrons. The conjugate base of a Brønsted–Lowry acid is also a Lewis base as <a href="/wiki/Deprotonation" title="Deprotonation">loss of H<sup>+</sup></a> from the acid leaves those electrons which were used for the A—H bond as a lone pair on the conjugate base. However, a Lewis base can be very difficult to <a href="/wiki/Protonation" title="Protonation">protonate</a>, yet still react with a Lewis acid. For example, <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> is a very weak Brønsted–Lowry base but it forms a strong adduct with BF<sub>3</sub>. </p><p>In another comparison of Lewis and Brønsted–Lowry acidity by Brown and Kanner,<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> 2,6-di-<i>t</i>-butylpyridine reacts to form the hydrochloride salt with HCl but does not react with BF<sub>3</sub>. This example demonstrates that steric factors, in addition to electron configuration factors, play a role in determining the strength of the interaction between the bulky di-<i>t</i>-butylpyridine and tiny proton. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=14" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Acid" title="Acid">Acid</a></li> <li><a href="/wiki/Base_(chemistry)" title="Base (chemistry)">Base (chemistry)</a></li> <li><a href="/wiki/Acid%E2%80%93base_reaction" title="Acid–base reaction">Acid–base reaction</a></li> <li><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></li> <li><a href="/wiki/Chiral_Lewis_acid" title="Chiral Lewis acid">Chiral Lewis acid</a></li> <li><a href="/wiki/Frustrated_Lewis_pair" title="Frustrated Lewis pair">Frustrated Lewis pair</a></li> <li><a href="/wiki/Gutmann%E2%80%93Beckett_method" title="Gutmann–Beckett method">Gutmann–Beckett method</a></li> <li><a href="/wiki/ECW_model" title="ECW model">ECW model</a></li> <li><a href="/wiki/Philosophy_of_chemistry" title="Philosophy of chemistry">Philosophy of chemistry</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=15" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Gold_Book_Lewis_acid_L03508-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Gold_Book_Lewis_acid_L03508_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Gold_Book_Lewis_acid_L03508_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/L03508.html">Lewis acid</a>". <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><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.L03508">10.1351/goldbook.L03508</a></span> </li> <li id="cite_note-lewisvalence-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-lewisvalence_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-lewisvalence_2-1"><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="CITEREFLewis1923" class="citation book cs1">Lewis, Gilbert Newton (1923). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=2hxDAAAAIAAJ&pg=PA142"><i>Valence and the Structure of Atoms and Molecules</i></a>. American chemical society. Monograph series. New York, New York, U.S.A.: Chemical Catalog Company. p. 142. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780598985408" title="Special:BookSources/9780598985408"><bdi>9780598985408</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Valence+and+the+Structure+of+Atoms+and+Molecules&rft.place=New+York%2C+New+York%2C+U.S.A.&rft.series=American+chemical+society.+Monograph+series&rft.pages=142&rft.pub=Chemical+Catalog+Company&rft.date=1923&rft.isbn=9780598985408&rft.aulast=Lewis&rft.aufirst=Gilbert+Newton&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D2hxDAAAAIAAJ%26pg%3DPA142&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" class="Z3988"></span> From p. 142: "We are inclined to think of substances as possessing acid or basic properties, without having a particular solvent in mind. It seems to me that with complete generality we may say that <i>a basic substance is one which has a lone pair of electrons which may be used to complete the stable group of another atom</i>, and that <i>an acid substance is one which can employ a lone pair from another molecule</i> in completing the stable group of one of its own atoms. In other words, the basic substance furnishes a pair of electrons for a chemical bond, the acid substance accepts such a pair."</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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAnslyn,_Eric_V.2006" class="citation book cs1">Anslyn, Eric V. (2006). <i>Modern physical organic chemistry</i>. Dougherty, Dennis A., 1952-. Sausalito, CA: University Science. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/1891389319" title="Special:BookSources/1891389319"><bdi>1891389319</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/55600610">55600610</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Modern+physical+organic+chemistry&rft.place=Sausalito%2C+CA&rft.pub=University+Science&rft.date=2006&rft_id=info%3Aoclcnum%2F55600610&rft.isbn=1891389319&rft.au=Anslyn%2C+Eric+V.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" class="Z3988"></span><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (September 2021)">page needed</span></a></i>]</sup></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLepetitMaravalCanacChauvin2016" class="citation journal cs1">Lepetit, Christine; Maraval, Valérie; Canac, Yves; Chauvin, Remi (2016). "On the Nature of the Dative Bond: Coordination to Metals and Beyond. The Carbon Case". <i>Coordination Chemistry Reviews</i>. <b>308</b>: 59–75. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ccr.2015.07.018">10.1016/j.ccr.2015.07.018</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Coordination+Chemistry+Reviews&rft.atitle=On+the+Nature+of+the+Dative+Bond%3A+Coordination+to+Metals+and+Beyond.+The+Carbon+Case&rft.volume=308&rft.pages=59-75&rft.date=2016&rft_id=info%3Adoi%2F10.1016%2Fj.ccr.2015.07.018&rft.aulast=Lepetit&rft.aufirst=Christine&rft.au=Maraval%2C+Val%C3%A9rie&rft.au=Canac%2C+Yves&rft.au=Chauvin%2C+Remi&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" class="Z3988"></span></span> </li> <li id="cite_note-March-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-March_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-March_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">March, J. “Advanced Organic Chemistry” 4th Ed. J. Wiley and Sons, 1992: New York. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-60180-2" title="Special:BookSources/0-471-60180-2">0-471-60180-2</a>.<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (September 2021)">page needed</span></a></i>]</sup></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="CITEREFVollhardt2018" class="citation book cs1">Vollhardt, K. Peter C. (2018). <i>Organic chemistry : structure and function</i>. Neil Eric Schore (8th ed.). New York. p. 73. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-319-07945-1" title="Special:BookSources/978-1-319-07945-1"><bdi>978-1-319-07945-1</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/1007924903">1007924903</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+chemistry+%3A+structure+and+function&rft.place=New+York&rft.pages=73&rft.edition=8th&rft.date=2018&rft_id=info%3Aoclcnum%2F1007924903&rft.isbn=978-1-319-07945-1&rft.aulast=Vollhardt&rft.aufirst=K.+Peter+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: location missing publisher (<a href="/wiki/Category:CS1_maint:_location_missing_publisher" title="Category:CS1 maint: location missing publisher">link</a>)</span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCarey2003" class="citation book cs1">Carey, Francis A. (2003). <i>Organic chemistry</i> (5th ed.). Boston: McGraw-Hill. p. 46. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-07-242458-3" title="Special:BookSources/0-07-242458-3"><bdi>0-07-242458-3</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/48850987">48850987</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+chemistry&rft.place=Boston&rft.pages=46&rft.edition=5th&rft.pub=McGraw-Hill&rft.date=2003&rft_id=info%3Aoclcnum%2F48850987&rft.isbn=0-07-242458-3&rft.aulast=Carey&rft.aufirst=Francis+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/E02020.html">Electrophile (Electrophilic)</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.E02020">10.1351/goldbook.E02020</a></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="CITEREFRowsellGillespieHeard1999" class="citation journal cs1">Rowsell, Bryan D.; Gillespie, Ronald J.; Heard, George L. (1999). "Ligand Close-Packing and the Lewis Acidity of BF3 and BCl3". <i>Inorganic Chemistry</i>. <b>38</b> (21): 4659–4662. <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%2Fic990713m">10.1021/ic990713m</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11671188">11671188</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Inorganic+Chemistry&rft.atitle=Ligand+Close-Packing+and+the+Lewis+Acidity+of+BF3+and+BCl3&rft.volume=38&rft.issue=21&rft.pages=4659-4662&rft.date=1999&rft_id=info%3Adoi%2F10.1021%2Fic990713m&rft_id=info%3Apmid%2F11671188&rft.aulast=Rowsell&rft.aufirst=Bryan+D.&rft.au=Gillespie%2C+Ronald+J.&rft.au=Heard%2C+George+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" 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">Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry of the Elements (2nd Edn.), Oxford:Butterworth-Heinemann. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-7506-3365-4" title="Special:BookSources/0-7506-3365-4">0-7506-3365-4</a>.<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (September 2021)">page needed</span></a></i>]</sup></span> </li> <li id="cite_note-hydron-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-hydron_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-hydron_11-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-hydron_11-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">Traditionally, but not precisely, <a href="/wiki/Hydron_(chemistry)" title="Hydron (chemistry)">H<sup>+</sup> ions</a> are referred as "<a href="/wiki/Proton" title="Proton">protons</a>". See <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/H02904.html">hydron</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.H02904">10.1351/goldbook.H02904</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">Christian Laurence and Jean-François Gal "Lewis Basicity and Affinity Scales : Data and Measurement" Wiley, 2009. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-74957-9" title="Special:BookSources/978-0-470-74957-9">978-0-470-74957-9</a>.<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (September 2021)">page needed</span></a></i>]</sup></span> </li> <li id="cite_note-CompAsymmetricCatalysis-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-CompAsymmetricCatalysis_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJacobsenPfaltzYamamato1999" class="citation book cs1">Jacobsen, E.N.; Pfaltz, Andreas; Yamamato, H., eds. (1999). <i>Comprehensive Asymmetric Catalysis</i>. Berlin; New York: Springer. pp. 1443–1445. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-64336-4" title="Special:BookSources/978-3-540-64336-4"><bdi>978-3-540-64336-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Comprehensive+Asymmetric+Catalysis&rft.place=Berlin%3B+New+York&rft.pages=1443-1445&rft.pub=Springer&rft.date=1999&rft.isbn=978-3-540-64336-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChildsMulhollandNixon1982" class="citation journal cs1">Childs, R.F; Mulholland, D.L; Nixon, A. (1982). <a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fv82-117">"Lewis acid adducts of α,β-unsaturated carbonyl and nitrile compounds. A nuclear magnetic resonance study"</a>. <i>Can. J. Chem</i>. <b>60</b> (6): 801–808. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fv82-117">10.1139/v82-117</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Can.+J.+Chem.&rft.atitle=Lewis+acid+adducts+of+%CE%B1%2C%CE%B2-unsaturated+carbonyl+and+nitrile+compounds.+A+nuclear+magnetic+resonance+study&rft.volume=60&rft.issue=6&rft.pages=801-808&rft.date=1982&rft_id=info%3Adoi%2F10.1139%2Fv82-117&rft.aulast=Childs&rft.aufirst=R.F&rft.au=Mulholland%2C+D.L&rft.au=Nixon%2C+A.&rft_id=https%3A%2F%2Fdoi.org%2F10.1139%252Fv82-117&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" 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="CITEREFVogelDrago1996" class="citation journal cs1">Vogel, Glenn C.; Drago, Russell S. (1996). "The ECW Model". <i>Journal of Chemical Education</i>. <b>73</b> (8): 701. <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&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chemical+Education&rft.atitle=The+ECW+Model&rft.volume=73&rft.issue=8&rft.pages=701&rft.date=1996&rft_id=info%3Adoi%2F10.1021%2Fed073p701&rft_id=info%3Abibcode%2F1996JChEd..73..701V&rft.aulast=Vogel&rft.aufirst=Glenn+C.&rft.au=Drago%2C+Russell+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" 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 id="CITEREFCramerBopp1977" class="citation journal cs1">Cramer, Roger E.; Bopp, Thomas T. (1977). "Great e and C plot. Graphical display of the enthalpies of adduct formation for Lewis acids and bases". <i>Journal of Chemical Education</i>. <b>54</b> (10): 612. <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/1977JChEd..54..612C">1977JChEd..54..612C</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%2Fed054p612">10.1021/ed054p612</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chemical+Education&rft.atitle=Great+e+and+C+plot.+Graphical+display+of+the+enthalpies+of+adduct+formation+for+Lewis+acids+and+bases&rft.volume=54&rft.issue=10&rft.pages=612&rft.date=1977&rft_id=info%3Adoi%2F10.1021%2Fed054p612&rft_id=info%3Abibcode%2F1977JChEd..54..612C&rft.aulast=Cramer&rft.aufirst=Roger+E.&rft.au=Bopp%2C+Thomas+T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" class="Z3988"></span></span> </li> <li id="cite_note-lewis_1-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-lewis_1_17-0">^</a></b></span> <span class="reference-text">Miessler, L. M., Tar, D. A., (1991) p. 166 – Table of discoveries attributes the date of publication/release for the Lewis theory as 1923.</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="CITEREFLewis1916" class="citation journal cs1">Lewis, Gilbert N. (April 1916). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=hvd.hs1t2w;view=1up;seq=772">"The atom and the molecule"</a>. <i>Journal of the American Chemical Society</i>. <b>38</b> (4): 762–785. <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%2Fja02261a002">10.1021/ja02261a002</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:95865413">95865413</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=The+atom+and+the+molecule&rft.volume=38&rft.issue=4&rft.pages=762-785&rft.date=1916-04&rft_id=info%3Adoi%2F10.1021%2Fja02261a002&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A95865413%23id-name%3DS2CID&rft.aulast=Lewis&rft.aufirst=Gilbert+N.&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dhvd.hs1t2w%3Bview%3D1up%3Bseq%3D772&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" 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 id="CITEREFBrownKanner1966" class="citation journal cs1">Brown, Herbert C.; Kanner, Bernard (1966). "Preparation and Reactions of 2,6-Di-t-butylpyridine and Related Hindered Bases. A Case of Steric Hindrance toward the Proton". <i>Journal of the American Chemical Society</i>. <b>88</b> (5): 986–992. <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%2Fja00957a023">10.1021/ja00957a023</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Preparation+and+Reactions+of+2%2C6-Di-t-butylpyridine+and+Related+Hindered+Bases.+A+Case+of+Steric+Hindrance+toward+the+Proton&rft.volume=88&rft.issue=5&rft.pages=986-992&rft.date=1966&rft_id=info%3Adoi%2F10.1021%2Fja00957a023&rft.aulast=Brown&rft.aufirst=Herbert+C.&rft.au=Kanner%2C+Bernard&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lewis_acids_and_bases&action=edit&section=16" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJensen1980" class="citation book cs1"><a href="/wiki/William_B._Jensen" title="William B. Jensen">Jensen, W.B.</a> (1980). <i>The Lewis acid-base concepts : an overview</i>. New York: Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-03902-0" title="Special:BookSources/0-471-03902-0"><bdi>0-471-03902-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Lewis+acid-base+concepts+%3A+an+overview&rft.place=New+York&rft.pub=Wiley&rft.date=1980&rft.isbn=0-471-03902-0&rft.aulast=Jensen&rft.aufirst=W.B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYamamoto1999" class="citation book cs1">Yamamoto, Hisashi (1999). <i>Lewis acid reagents : a practical approach</i>. New York: Oxford University Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-19-850099-8" title="Special:BookSources/0-19-850099-8"><bdi>0-19-850099-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lewis+acid+reagents+%3A+a+practical+approach&rft.place=New+York&rft.pub=Oxford+University+Press&rft.date=1999&rft.isbn=0-19-850099-8&rft.aulast=Yamamoto&rft.aufirst=Hisashi&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALewis+acids+and+bases" class="Z3988"></span></li></ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Lewis_acids_and_bases&oldid=1253170813">https://en.wikipedia.org/w/index.php?title=Lewis_acids_and_bases&oldid=1253170813</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Acid%E2%80%93base_chemistry" title="Category:Acid–base chemistry">Acid–base chemistry</a></li><li><a href="/wiki/Category:Acids" title="Category:Acids">Acids</a></li><li><a href="/wiki/Category:Bases_(chemistry)" title="Category:Bases (chemistry)">Bases (chemistry)</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Wikipedia_articles_needing_page_number_citations_from_September_2021" title="Category:Wikipedia articles needing page number citations from September 2021">Wikipedia articles needing page number citations from September 2021</a></li><li><a href="/wiki/Category:CS1_maint:_location_missing_publisher" title="Category:CS1 maint: location missing publisher">CS1 maint: location missing publisher</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li><li><a href="/wiki/Category:All_articles_with_unsourced_statements" title="Category:All articles with unsourced statements">All articles with unsourced statements</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_January_2024" title="Category:Articles with unsourced statements from January 2024">Articles with unsourced statements from January 2024</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 24 October 2024, at 17:47<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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