{"id":13268,"date":"2026-09-12T23:00:54","date_gmt":"2026-09-12T17:30:54","guid":{"rendered":"https:\/\/bijmrd.com\/?p=13268"},"modified":"2026-10-15T00:32:35","modified_gmt":"2026-10-14T19:02:35","slug":"sulfur-centered-nucleophilic-aromatic-substitution-mechanistic-pathways-substrate-scope-and-practical-constraints-with-emphasis-on-ethyl-3-mercaptopropionate","status":"publish","type":"post","link":"https:\/\/bijmrd.com\/index.php\/volume4-issue8\/sulfur-centered-nucleophilic-aromatic-substitution-mechanistic-pathways-substrate-scope-and-practical-constraints-with-emphasis-on-ethyl-3-mercaptopropionate\/","title":{"rendered":"Sulfur-Centered Nucleophilic Aromatic Substitution: Mechanistic Pathways, Substrate Scope and Practical Constraints with Emphasis on Ethyl 3-Mercaptopropionate"},"content":{"rendered":"\n

Author: Prasenjit Bera & Dr. Koomkoom Khawas<\/strong><\/p>\n\n\n\n

DOI Link:<\/strong> https:\/\/doi.org\/10.70798\/Bijmrd\/04080022<\/a><\/p>\n\n\n\n

Abstract:<\/strong> Nucleophilic aromatic substitution (SNAr) is an important synthetic approach for constructing carbon\u2013sulfur bonds in electron-deficient aromatic systems. This critical review explores the mechanistic pathways, substrate scope, reactivity, selectivity, and practical limitations of sulfur-mediated SNAr reactions, with particular emphasis on ethyl 3-mercaptopropionate (HS\u2013CH\u2082\u2013CH\u2082\u2013CO\u2082Et). Key factors influencing reaction efficiency, including electron-withdrawing substituents, leaving-group identity, solvent polarity, base strength, and temperature, are critically examined. Classical addition\u2013elimination mechanisms involving Meisenheimer intermediates are compared with concerted SNAr pathways. Literature-based kinetic and computational findings are discussed alongside applications in aromatic functionalization and heterocyclic chemistry. Potential challenges, including thiol oxidation, incomplete deprotonation, ester hydrolysis, and product selectivity, are highlighted. The review identifies existing research gaps and proposes integrated kinetic, spectroscopic, and computational approaches to improve mechanistic understanding and reaction reproducibility. Overall, this analysis provides valuable insights into the development of efficient and selective sulfur-based SNAr methodologies.<\/p>\n\n\n\n

Keywords:<\/strong> Nucleophilic aromatic substitution (SNAr); Ethyl 3-mercaptopropionate; Sulfur nucleophiles; Thiolate ions; Aryl\u2013sulfur bond formation; Meisenheimer intermediate; Reaction kinetics; Density functional theory; Structure\u2013reactivity relationships; Porphyrinoids.<\/p>\n\n\n\n

Page No: 179-201<\/strong><\/p>\n\n\n\n

\n
download journal<\/a><\/div>\n<\/div>\n","protected":false},"excerpt":{"rendered":"

Author: Prasenjit Bera & Dr. Koomkoom Khawas DOI Link: https:\/\/doi.org\/10.70798\/Bijmrd\/04080022 Abstract: Nucleophilic aromatic substitution (SNAr) is an important synthetic approach for constructing carbon\u2013sulfur bonds in electron-deficient aromatic systems. This critical review explores the mechanistic pathways, substrate scope, reactivity, selectivity, and practical limitations of sulfur-mediated SNAr reactions, with particular emphasis on ethyl 3-mercaptopropionate (HS\u2013CH\u2082\u2013CH\u2082\u2013CO\u2082Et). Key factors …<\/p>\n

Sulfur-Centered Nucleophilic Aromatic Substitution: Mechanistic Pathways, Substrate Scope and Practical Constraints with Emphasis on Ethyl 3-Mercaptopropionate<\/span> Read More »<\/a><\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"default","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"set","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"tablet":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"mobile":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""}},"ast-content-background-meta":{"desktop":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"tablet":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"mobile":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""}},"footnotes":"","_joinchat":[]},"categories":[64],"tags":[],"rttpg_featured_image_url":null,"rttpg_author":{"display_name":false,"author_link":"https:\/\/bijmrd.com\/index.php\/author\/asraful-alibiswas\/"},"rttpg_comment":0,"rttpg_category":"Volume4 Issue8<\/a>","rttpg_excerpt":"Author: Prasenjit Bera & Dr. Koomkoom Khawas DOI Link: https:\/\/doi.org\/10.70798\/Bijmrd\/04080022 Abstract: Nucleophilic aromatic substitution (SNAr) is an important synthetic approach for constructing carbon\u2013sulfur bonds in electron-deficient aromatic systems. This critical review explores the mechanistic pathways, substrate scope, reactivity, selectivity, and practical limitations of sulfur-mediated SNAr reactions, with particular emphasis on ethyl 3-mercaptopropionate (HS\u2013CH\u2082\u2013CH\u2082\u2013CO\u2082Et). Key factors…","_links":{"self":[{"href":"https:\/\/bijmrd.com\/index.php\/wp-json\/wp\/v2\/posts\/13268"}],"collection":[{"href":"https:\/\/bijmrd.com\/index.php\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/bijmrd.com\/index.php\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/bijmrd.com\/index.php\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/bijmrd.com\/index.php\/wp-json\/wp\/v2\/comments?post=13268"}],"version-history":[{"count":1,"href":"https:\/\/bijmrd.com\/index.php\/wp-json\/wp\/v2\/posts\/13268\/revisions"}],"predecessor-version":[{"id":13269,"href":"https:\/\/bijmrd.com\/index.php\/wp-json\/wp\/v2\/posts\/13268\/revisions\/13269"}],"wp:attachment":[{"href":"https:\/\/bijmrd.com\/index.php\/wp-json\/wp\/v2\/media?parent=13268"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/bijmrd.com\/index.php\/wp-json\/wp\/v2\/categories?post=13268"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/bijmrd.com\/index.php\/wp-json\/wp\/v2\/tags?post=13268"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}