{"id":47867,"date":"2023-09-07T14:37:56","date_gmt":"2023-09-07T08:52:56","guid":{"rendered":"https:\/\/thechemistrynotes.com\/?p=47867"},"modified":"2023-09-07T14:37:59","modified_gmt":"2023-09-07T08:52:59","slug":"diazotization-reaction-mechanism-application","status":"publish","type":"post","link":"https:\/\/thechemistrynotes.com\/diazotization-reaction-mechanism-application\/","title":{"rendered":"Diazotization Reaction: Definition, Mechanism, Applications"},"content":{"rendered":"\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"536\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Diazotization-reaction-1024x536.jpg\" alt=\"Diazotization reaction\" class=\"wp-image-47872\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Diazotization-reaction-1024x536.jpg 1024w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Diazotization-reaction-300x157.jpg 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Diazotization-reaction-768x402.jpg 768w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Diazotization-reaction.jpg 1205w\" sizes=\"(max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<p>Diazotization reaction is the reaction that produces diazonium ions from aromatic amines. The process of creating a diazonium salt or diazonium compound is known as diazotization. An aromatic amine combines with a reagent having a nitrosyl cation (NO) or a reagent capable of generating the appropriate aryldiazonium salt in this organic process. Diazotization is the chemical process that converts a primary aromatic amine into its equivalent diazonium salt.<\/p>\n\n\n\n<p>In 1858, the German industrial chemist Peter Griess was the first to report such a reaction. He went on to find many more diazonium salt reactions.<\/p>\n\n\n\n<p>These diazonium salts are often created by reacting an aromatic amine with nitrous acid in the presence of another acid. For example, in the process below, aniline interacts with sodium nitrite and hydrochloric acid to generate nitrous acid. At temperatures ranging from 0 to 5\u00b0C, the nitrous acid interacts with aniline to create diazonium ions. Tetrazotization refers to the diazotization of bifunctional aromatic amines (for example, p-phenylenediamine or benzidine).<\/p>\n\n\n\n<div id=\"ez-toc-container\" class=\"ez-toc-v2_0_64 counter-hierarchy ez-toc-counter ez-toc-custom ez-toc-container-direction\">\n<div class=\"ez-toc-title-container\">\n<p class=\"ez-toc-title \" >Table of Contents<\/p>\n<span class=\"ez-toc-title-toggle\"><a href=\"#\" class=\"ez-toc-pull-right ez-toc-btn ez-toc-btn-xs ez-toc-btn-default ez-toc-toggle\" aria-label=\"Toggle Table of Content\"><span class=\"ez-toc-js-icon-con\"><span class=\"\"><span class=\"eztoc-hide\" style=\"display:none;\">Toggle<\/span><span class=\"ez-toc-icon-toggle-span\"><svg style=\"fill: #0a0a0a;color:#0a0a0a\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" class=\"list-377408\" width=\"20px\" height=\"20px\" viewBox=\"0 0 24 24\" fill=\"none\"><path d=\"M6 6H4v2h2V6zm14 0H8v2h12V6zM4 11h2v2H4v-2zm16 0H8v2h12v-2zM4 16h2v2H4v-2zm16 0H8v2h12v-2z\" fill=\"currentColor\"><\/path><\/svg><svg style=\"fill: #0a0a0a;color:#0a0a0a\" class=\"arrow-unsorted-368013\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" width=\"10px\" height=\"10px\" viewBox=\"0 0 24 24\" version=\"1.2\" baseProfile=\"tiny\"><path d=\"M18.2 9.3l-6.2-6.3-6.2 6.3c-.2.2-.3.4-.3.7s.1.5.3.7c.2.2.4.3.7.3h11c.3 0 .5-.1.7-.3.2-.2.3-.5.3-.7s-.1-.5-.3-.7zM5.8 14.7l6.2 6.3 6.2-6.3c.2-.2.3-.5.3-.7s-.1-.5-.3-.7c-.2-.2-.4-.3-.7-.3h-11c-.3 0-.5.1-.7.3-.2.2-.3.5-.3.7s.1.5.3.7z\"\/><\/svg><\/span><\/span><\/span><\/a><\/span><\/div>\n<nav><ul class='ez-toc-list ez-toc-list-level-1 ' ><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-1\" href=\"https:\/\/thechemistrynotes.com\/diazotization-reaction-mechanism-application\/#what-is-the-diazotization-reaction\" title=\"What is the Diazotization reaction?\">What is the Diazotization reaction?<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-2\" href=\"https:\/\/thechemistrynotes.com\/diazotization-reaction-mechanism-application\/#mechanism-of-diazotization-reaction\" title=\"Mechanism of Diazotization reaction\">Mechanism of Diazotization reaction<\/a><ul class='ez-toc-list-level-3' ><li class='ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-3\" href=\"https:\/\/thechemistrynotes.com\/diazotization-reaction-mechanism-application\/#generation-of-nitrosonium-ion\" title=\"Generation of nitrosonium ion\">Generation of nitrosonium ion<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-4\" href=\"https:\/\/thechemistrynotes.com\/diazotization-reaction-mechanism-application\/#formation-of-benzene-diazonium-ion\" title=\"Formation of benzene diazonium ion\">Formation of benzene diazonium ion<\/a><\/li><\/ul><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-5\" href=\"https:\/\/thechemistrynotes.com\/diazotization-reaction-mechanism-application\/#applications-of-diazotization-reaction\" title=\"Applications of Diazotization Reaction\">Applications of Diazotization Reaction<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-6\" href=\"https:\/\/thechemistrynotes.com\/diazotization-reaction-mechanism-application\/#references\" title=\"References\">References<\/a><\/li><\/ul><\/nav><\/div>\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"what-is-the-diazotization-reaction\"><\/span><strong>What is the Diazotization reaction?<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<p>Aromatic amines react with nitric acid and mineral acids to make diazonium salts, and water is produced as a byproduct. This is referred to as the diazotization reaction.<\/p>\n\n\n<div class=\"wp-block-image\">\n<figure class=\"aligncenter size-full is-resized\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-32.png\" alt=\"\" class=\"wp-image-47870\" style=\"width:448px;height:160px\" width=\"448\" height=\"160\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-32.png 705w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-32-300x107.png 300w\" sizes=\"(max-width: 448px) 100vw, 448px\" \/><\/figure><\/div>\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"mechanism-of-diazotization-reaction\"><\/span><strong>Mechanism of Diazotization reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<p>When primary amine is treated with nitrous acid, the&nbsp;diazonium salt is formed, which is a compound of the type Ar\/R-NN<sup>+<\/sup> X<sup>&#8211;<\/sup>, where X- is an anion such as chloride, bromide, sulfate, and so on. However, because nitrous acid is unstable, it is produced in situ by treating sodium nitrite with a strong acid such as HCl or H<sub>2<\/sub>SO<sub>4<\/sub>. Diazotization is the process of converting primary amine to its diazonium salt.<\/p>\n\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"generation-of-nitrosonium-ion\"><\/span><strong>Generation of nitrosonium ion<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>The production method of diazonium salts involves the addition of NO, followed by a sequence of acid-base events that convert the oxygen into water and establish a triple bond between the two nitrogens. Afterward, the water is released as a leaving group.<\/p>\n\n\n\n<p>The unstable nitrous acid must first be produced by treating sodium nitrite with aqueous HCl. Nitrous acid is formed by protonating a nitrite ion with HCl. The nitrous acid is then protonated to produce an oxonium ion with a suitable leaving group (water). Finally, the removal of the\u00a0leaving group\u00a0results in the formation of nitrosonium ion\u00a0or nitrosyl cation.<\/p>\n\n\n\n<figure class=\"wp-block-image size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"975\" height=\"530\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-30.png\" alt=\"\" class=\"wp-image-47868\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-30.png 975w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-30-300x163.png 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-30-768x417.png 768w\" sizes=\"(max-width: 975px) 100vw, 975px\" \/><\/figure>\n\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"formation-of-benzene-diazonium-ion\"><\/span><strong>Formation of benzene diazonium ion<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>The nitrosonium ion is electrophilic, and amines can attack it to create an N-nitrosonium salt. When water deprotonates this nitrosammonium ion, a stable intermediate (N-nitrosamine) is generated. The oxygen atom of N-nitrosamine is then protonated, and water removes a proton from the nitrogen atom to form a double bond between the nitrogen atoms. The oxygen atom is protonated once more, resulting in a good leaving group (water). The departure\u00a0of water results in the formation of a diazonium ion.<\/p>\n\n\n\n<figure class=\"wp-block-image size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"940\" height=\"425\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-31.png\" alt=\"\" class=\"wp-image-47869\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-31.png 940w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-31-300x136.png 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-31-768x347.png 768w\" sizes=\"(max-width: 940px) 100vw, 940px\" \/><\/figure>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"applications-of-diazotization-reaction\"><\/span><strong>Applications of<\/strong> <strong>Diazotization Reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ul>\n<li>Diazotization reactions are commonly used in the synthesis of azo dyes. Azo dyes are a type of organic compound that is widely utilized in the textile, printing, and coloring industries.<\/li>\n\n\n\n<li>Various colored azo compounds can be synthesized by diazotizing an aromatic amine and coupling it with a suitable coupling agent.<\/li>\n\n\n\n<li>Aryl halides, such as aryl chlorides or aryl bromides, can be created from aromatic amines through the Diazotization reaction.5<\/li>\n\n\n\n<li>In the production of medicinal substances, diazotization processes are used. The resulting diazonium salts can be reacted with a variety of nucleophiles, including <a href=\"https:\/\/thechemistrynotes.com\/phenol-classification-preparation-properties-reactions-uses\/\">phenols<\/a>, amines, and thiols, to form pharmaceutical intermediates or active pharmaceutical ingredients (APIs).<\/li>\n\n\n\n<li>Diazonium compounds are common reagents in the synthesis of organic molecules.<\/li>\n\n\n\n<li>Diazonium salts have the potential to be employed in nanotechnology. They help single-walled nanotubes to be functionalized effectively.<\/li>\n\n\n\n<li>Aromatic fluorides can also be produced through diazotization processes.<\/li>\n<\/ul>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"references\"><\/span><strong>References<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ul>\n<li>Morrison R. T. &amp; Boyd R. N. (1983).&nbsp;<em>Organic chemistry<\/em>&nbsp;(4th ed.). Allyn and Bacon.<\/li>\n\n\n\n<li>Smith M. &amp; March J. (2001).&nbsp;<em>March\u2019s Advanced Organic Chemistry: Reactions Mechanisms and Structure<\/em>&nbsp;(5th ed.). Wiley.<\/li>\n\n\n\n<li>Ghosh, S.K.,&nbsp;<em>Advanced General Organic Chemistry<\/em>, Second Edition, New Central Book Agency Pvt. Ltd., Kolkatta, 2007.<\/li>\n\n\n\n<li>Bahl, B.S., A., Advanced Organic Chemistry, S. Chand and Company Ltd, New Delhi, 1992. production of polyesters, polyurethanes, and alkaline resins.<\/li>\n<\/ul>\n\n\n\n<p><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Diazotization reaction is the reaction that produces diazonium ions from aromatic amines. The process of creating a diazonium salt or diazonium compound is known as diazotization. An aromatic amine combines &#8230; <a title=\"Diazotization Reaction: Definition, Mechanism, Applications\" class=\"read-more\" href=\"https:\/\/thechemistrynotes.com\/diazotization-reaction-mechanism-application\/\" aria-label=\"Read more about Diazotization Reaction: Definition, Mechanism, Applications\">Read more<\/a><\/p>\n","protected":false},"author":4,"featured_media":47872,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[21],"tags":[2870,2868,2869],"_links":{"self":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/47867"}],"collection":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/users\/4"}],"replies":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/comments?post=47867"}],"version-history":[{"count":2,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/47867\/revisions"}],"predecessor-version":[{"id":47873,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/47867\/revisions\/47873"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/media\/47872"}],"wp:attachment":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/media?parent=47867"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/categories?post=47867"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/tags?post=47867"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}