{"id":{"repo_id":"unt","oai_identifier":"info:ark/67531/metadc4415"},"canonical_url":"https://search.dev.ndltd.org/etd/unt/info:ark/67531/metadc4415","repository":{"repo_id":"unt","name":"University of North Texas","base_url":"https://digital.library.unt.edu/oai/"},"display":{"title":"Synthesis and characterization of 2-chloro-3-benzylthiopyrrolo[1,2-a]- benzimidazol-1-one and 2,3-di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one.","abstract":"The reaction between o-phenylenediamine and 2,3-dichloromaleic anhydride has been probed and found to give 2,3-dichloropyrrolo[1,2-a]- benzimidazol-1-one as the major product. Chlorine substitution in 2,3-dichloropyrrolo[1,2-a]benzimidazol-1-one by added benzylthiol occurs in the presence of pyridine to provide the corresponding monosulfide and disulfide derivatives. The first benzylthiol ligand undergoes reaction at the C-3 position of the five-membered pyrrolo-1-one ring, with the addition of the second benzylthiol ligand occurring at the remaining chlorine-substituted carbon. The mono- and disulfide derivatives have been isolated and characterized in solution by NMR, IR, and UV-vis spectroscopies, and the solid-state structure of 2,3-di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one has been established by X-ray crystallography.","abstract_html":"The reaction between o-phenylenediamine and 2,3-dichloromaleic anhydride has been probed and found to give 2,3-dichloropyrrolo[1,2-a]- benzimidazol-1-one as the major product. Chlorine substitution in 2,3-dichloropyrrolo[1,2-a]benzimidazol-1-one by added benzylthiol occurs in the presence of pyridine to provide the corresponding monosulfide and disulfide derivatives. The first benzylthiol ligand undergoes reaction at the C-3 position of the five-membered pyrrolo-1-one ring, with the addition of the second benzylthiol ligand occurring at the remaining chlorine-substituted carbon. The mono- and disulfide derivatives have been isolated and characterized in solution by NMR, IR, and UV-vis spectroscopies, and the solid-state structure of 2,3-di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one has been established by X-ray crystallography.","abstract_has_math":false,"creators":["Huang, Shih-Huang"],"institution":"University of North Texas","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":["Richmond, Michael","Mason, Diana"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2003,"date_issued":"2003-12","date_published":"2003-12","updated_at":"2026-07-24T05:35:09Z","subjects":["Chlorine compounds.","Crystallography.","2,3-Di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one","chlorine","crystallography","chlorine substitution","pyridine"],"languages":["English"],"rights":["Public","Copyright","Huang, Shih-Huang","Copyright is held by the author, unless otherwise noted. All rights reserved."],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["oclc: 54479642","https://digital.library.unt.edu/ark:/67531/metadc4415/","ark: ark:/67531/metadc4415"],"render_values":[{"text":"oclc: 54479642","href":null,"code":true},{"text":"https://digital.library.unt.edu/ark:/67531/metadc4415/","href":"https://digital.library.unt.edu/ark:/67531/metadc4415/","code":true},{"text":"ark: ark:/67531/metadc4415","href":null,"code":true}]}]},"links":{"outbound_url":"https://doi.org/10.12794/metadc4415","outbound_label":"DOI","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Richmond, Michael","Mason, Diana"]},{"key":"dc:creator","label":"Author","values":["Huang, Shih-Huang"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2003-12"]},{"key":"dc:publisher","label":"Institution","values":["University of North Texas"]},{"key":"dc:type","label":"Dc Type","values":["Thesis or Dissertation"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chlorine compounds.","Crystallography.","2,3-Di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one","chlorine","crystallography","chlorine substitution","pyridine"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["English"]},{"key":"dc:rights","label":"Dc Rights","values":["Public","Copyright","Huang, Shih-Huang","Copyright is held by the author, unless otherwise noted. All rights reserved."]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["oclc: 54479642","doi: 10.12794/metadc4415","https://digital.library.unt.edu/ark:/67531/metadc4415/","ark: ark:/67531/metadc4415"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["The reaction between o-phenylenediamine and 2,3-dichloromaleic anhydride has been probed and found to give 2,3-dichloropyrrolo[1,2-a]- benzimidazol-1-one as the major product. Chlorine substitution in 2,3-dichloropyrrolo[1,2-a]benzimidazol-1-one by added benzylthiol occurs in the presence of pyridine to provide the corresponding monosulfide and disulfide derivatives. The first benzylthiol ligand undergoes reaction at the C-3 position of the five-membered pyrrolo-1-one ring, with the addition of the second benzylthiol ligand occurring at the remaining chlorine-substituted carbon. The mono- and disulfide derivatives have been isolated and characterized in solution by NMR, IR, and UV-vis spectroscopies, and the solid-state structure of 2,3-di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one has been established by X-ray crystallography."]},{"key":"dc:format","label":"Dc Format","values":["Text"]},{"key":"dc:title","label":"Title","values":["Synthesis and characterization of 2-chloro-3-benzylthiopyrrolo[1,2-a]- benzimidazol-1-one and 2,3-di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one."]}]}],"canonical_facts":{"dc:contributor":["Richmond, Michael","Mason, Diana"],"dc:creator":["Huang, Shih-Huang"],"dc:date":["2003-12"],"dc:description":["The reaction between o-phenylenediamine and 2,3-dichloromaleic anhydride has been probed and found to give 2,3-dichloropyrrolo[1,2-a]- benzimidazol-1-one as the major product. Chlorine substitution in 2,3-dichloropyrrolo[1,2-a]benzimidazol-1-one by added benzylthiol occurs in the presence of pyridine to provide the corresponding monosulfide and disulfide derivatives. The first benzylthiol ligand undergoes reaction at the C-3 position of the five-membered pyrrolo-1-one ring, with the addition of the second benzylthiol ligand occurring at the remaining chlorine-substituted carbon. The mono- and disulfide derivatives have been isolated and characterized in solution by NMR, IR, and UV-vis spectroscopies, and the solid-state structure of 2,3-di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one has been established by X-ray crystallography."],"dc:format":["Text"],"dc:identifier":["oclc: 54479642","doi: 10.12794/metadc4415","https://digital.library.unt.edu/ark:/67531/metadc4415/","ark: ark:/67531/metadc4415"],"dc:language":["English"],"dc:publisher":["University of North Texas"],"dc:rights":["Public","Copyright","Huang, Shih-Huang","Copyright is held by the author, unless otherwise noted. All rights reserved."],"dc:subject":["Chlorine compounds.","Crystallography.","2,3-Di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one","chlorine","crystallography","chlorine substitution","pyridine"],"dc:title":["Synthesis and characterization of 2-chloro-3-benzylthiopyrrolo[1,2-a]- benzimidazol-1-one and 2,3-di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one."],"dc:type":["Thesis or Dissertation"]},"updated_at":"2026-07-24T05:35:09Z"}