{"id":"https://openalex.org/W2000215285","doi":"https://doi.org/10.1080/08927022.2010.497926","title":"Kinetic and thermodynamic study of the substituent effect on the amino-Claisen rearrangement ofpara-substitutedN-allyl-N-arylamine: a Hammett study via DFT","display_name":"Kinetic and thermodynamic study of the substituent effect on the amino-Claisen rearrangement ofpara-substitutedN-allyl-N-arylamine: a Hammett study via DFT","publication_year":2010,"publication_date":"2010-10-01","ids":{"openalex":"https://openalex.org/W2000215285","doi":"https://doi.org/10.1080/08927022.2010.497926","mag":"2000215285"},"language":"en","primary_location":{"id":"doi:10.1080/08927022.2010.497926","doi":"https://doi.org/10.1080/08927022.2010.497926","is_oa":false,"landing_page_url":"https://doi.org/10.1080/08927022.2010.497926","pdf_url":null,"source":{"id":"https://openalex.org/S45504773","display_name":"Molecular Simulation","issn_l":"0892-7022","issn":["0892-7022","1026-7638","1029-0435"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","norway-1","poland-70","russia-white-list-1"],"host_organization":"https://openalex.org/P4310320547","host_organization_name":"Taylor & Francis","host_organization_lineage":["https://openalex.org/P4310320547","https://openalex.org/P4310320449"],"host_organization_lineage_names":["Taylor & Francis","Informa"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Molecular Simulation","raw_type":"journal-article"},"parent_works":[],"lineage":["https://openalex.org/W2000215285"],"child_works_count":0,"type":"article","is_traditional":true,"indexed_in":["crossref"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5088379495","display_name":"Saeedreza Emamian","orcid":"https://orcid.org/0000-0001-8223-1264","observed_orcids":["https://orcid.org/0000-0001-8223-1264"]},"institutions":[{"id":"https://openalex.org/I110525433","display_name":"Islamic Azad University, Tehran","ror":"https://ror.org/01kzn7k21","country_code":"IR","type":"education","lineage":["https://openalex.org/I110525433"]},{"id":"https://openalex.org/I155419210","display_name":"Islamic Azad University, Science and Research Branch","ror":"https://ror.org/03187yj51","country_code":"IR","type":"education","lineage":["https://openalex.org/I110525433","https://openalex.org/I155419210"]}],"countries":["IR"],"is_corresponding":false,"raw_author_name":"S.R. Emamian","raw_affiliation_strings":["Department of Chemistry, Research and Science Branch, Islamic Azad University, Tehran, Iran"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Research and Science Branch, Islamic Azad University, Tehran, Iran","institution_ids":["https://openalex.org/I110525433","https://openalex.org/I155419210"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5037189042","display_name":"Mehran Aghaie","orcid":"https://orcid.org/0000-0001-7393-6043","observed_orcids":["https://orcid.org/0000-0001-7393-6043"]},"institutions":[{"id":"https://openalex.org/I110525433","display_name":"Islamic Azad University, Tehran","ror":"https://ror.org/01kzn7k21","country_code":"IR","type":"education","lineage":["https://openalex.org/I110525433"]},{"id":"https://openalex.org/I183067279","display_name":"Islamic Azad University North Tehran Branch","ror":"https://ror.org/00sb1nr29","country_code":"IR","type":"education","lineage":["https://openalex.org/I110525433","https://openalex.org/I183067279"]}],"countries":["IR"],"is_corresponding":true,"raw_author_name":"M. Aghaie","raw_affiliation_strings":["Faculty of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Faculty of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran","institution_ids":["https://openalex.org/I110525433","https://openalex.org/I183067279"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5006896109","display_name":"Mohammad Reza Zardoost","orcid":"https://orcid.org/0000-0001-5623-1818","observed_orcids":["https://orcid.org/0000-0001-5623-1818"]},"institutions":[{"id":"https://openalex.org/I110525433","display_name":"Islamic Azad University, Tehran","ror":"https://ror.org/01kzn7k21","country_code":"IR","type":"education","lineage":["https://openalex.org/I110525433"]},{"id":"https://openalex.org/I155419210","display_name":"Islamic Azad University, Science and Research Branch","ror":"https://ror.org/03187yj51","country_code":"IR","type":"education","lineage":["https://openalex.org/I110525433","https://openalex.org/I155419210"]}],"countries":["IR"],"is_corresponding":false,"raw_author_name":"M.R. Zardoost","raw_affiliation_strings":["Department of Chemistry, Research and Science Branch, Islamic Azad University, Tehran, Iran"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Research and Science Branch, Islamic Azad University, Tehran, Iran","institution_ids":["https://openalex.org/I110525433","https://openalex.org/I155419210"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5024368037","display_name":"Ehsan Zahedi","orcid":"https://orcid.org/0000-0003-2386-3776","observed_orcids":["https://orcid.org/0000-0003-2386-3776"]},"institutions":[{"id":"https://openalex.org/I4210093808","display_name":"Islamic Azad University, Shahrood","ror":"https://ror.org/00j1sp553","country_code":"IR","type":"education","lineage":["https://openalex.org/I110525433","https://openalex.org/I4210093808"]}],"countries":["IR"],"is_corresponding":false,"raw_author_name":"E. Zahedi","raw_affiliation_strings":["Department of Chemistry, Shahrood Branch, Islamic Azad University, Shahrood, Iran"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Shahrood Branch, Islamic Azad University, Shahrood, Iran","institution_ids":["https://openalex.org/I4210093808"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5102810821","display_name":"Karim Zare","orcid":"https://orcid.org/0000-0002-6234-3303","observed_orcids":["https://orcid.org/0000-0002-6234-3303"]},"institutions":[{"id":"https://openalex.org/I110525433","display_name":"Islamic Azad University, Tehran","ror":"https://ror.org/01kzn7k21","country_code":"IR","type":"education","lineage":["https://openalex.org/I110525433"]},{"id":"https://openalex.org/I155419210","display_name":"Islamic Azad University, Science and Research Branch","ror":"https://ror.org/03187yj51","country_code":"IR","type":"education","lineage":["https://openalex.org/I110525433","https://openalex.org/I155419210"]}],"countries":["IR"],"is_corresponding":false,"raw_author_name":"K. Zare","raw_affiliation_strings":["Department of Chemistry, Research and Science Branch, Islamic Azad University, Tehran, Iran"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Research and Science Branch, Islamic Azad University, Tehran, Iran","institution_ids":["https://openalex.org/I110525433","https://openalex.org/I155419210"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":4,"corresponding_author_ids":["https://openalex.org/A5037189042"],"corresponding_institution_ids":["https://openalex.org/I110525433","https://openalex.org/I183067279"],"apc_list":null,"apc_paid":null,"fwci":0.5915,"has_fulltext":false,"cited_by_count":5,"citation_normalized_percentile":{"value":0.61868841,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":93},"biblio":{"volume":"36","issue":"12","first_page":"978","last_page":"985"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12191","display_name":"Physical Organic Chemistry and Reaction Kinetics","score":0.9916999936103821,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T12191","display_name":"Physical Organic Chemistry and Reaction Kinetics","score":0.9916999936103821,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12893","display_name":"Organic Chemistry Cycloaddition Reactions","score":0.005799999926239252,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T13253","display_name":"Photolysis and Reactive Intermediates","score":0.0003000000142492354,"subfield":{"id":"https://openalex.org/subfields/1606","display_name":"Physical and Theoretical Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/amino-claisen-rearrangement","display_name":"amino-Claisen rearrangement","score":0.9990000128746033},{"id":"https://openalex.org/keywords/para-substituent-effects","display_name":"para-substituent effects","score":0.8999999761581421},{"id":"https://openalex.org/keywords/hammett-equation","display_name":"Hammett correlation","score":0.8069999814033508},{"id":"https://openalex.org/keywords/activation-energy","display_name":"activation energy","score":0.6940000057220459},{"id":"https://openalex.org/keywords/transition-state","display_name":"transition state","score":0.7009999752044678},{"id":"https://openalex.org/keywords/entropy-of-activation","display_name":"activation entropy","score":0.7129999995231628},{"id":"https://openalex.org/keywords/concerted-mechanism","display_name":"concerted mechanism","score":0.8930000066757202},{"id":"https://openalex.org/keywords/electron-donating-substituents","display_name":"electron-donating substituents","score":0.7020000219345093},{"id":"https://openalex.org/keywords/electron-withdrawing-substituents","display_name":"electron-withdrawing substituents","score":0.9490000009536743},{"id":"https://openalex.org/keywords/reaction-kinetics","display_name":"reaction kinetics","score":0.6539999842643738},{"id":"https://openalex.org/keywords/reaction-thermodynamics","display_name":"reaction thermodynamics","score":0.9620000123977661}],"concepts":[{"id":"https://openalex.org/C2778689049","wikidata":"https://www.wikidata.org/wiki/Q898422","display_name":"Substituent","level":2,"score":0.8511107563972473},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7938779592514038},{"id":"https://openalex.org/C2780567667","wikidata":"https://www.wikidata.org/wiki/Q900936","display_name":"Claisen rearrangement","level":2,"score":0.7730579376220703},{"id":"https://openalex.org/C54516573","wikidata":"https://www.wikidata.org/wiki/Q2294","display_name":"Proton","level":2,"score":0.5988616943359375},{"id":"https://openalex.org/C8503813","wikidata":"https://www.wikidata.org/wiki/Q901637","display_name":"Hammett equation","level":4,"score":0.5698152184486389},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.4781721234321594},{"id":"https://openalex.org/C35396096","wikidata":"https://www.wikidata.org/wiki/Q3238654","display_name":"Polar effect","level":2,"score":0.42749521136283875},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.4175889790058136},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.3225668668746948},{"id":"https://openalex.org/C93391505","wikidata":"https://www.wikidata.org/wiki/Q658700","display_name":"Reaction rate constant","level":3,"score":0.2649121582508087},{"id":"https://openalex.org/C148898269","wikidata":"https://www.wikidata.org/wiki/Q1108792","display_name":"Kinetics","level":2,"score":0.17607328295707703},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.07657602429389954},{"id":"https://openalex.org/C62520636","wikidata":"https://www.wikidata.org/wiki/Q944","display_name":"Quantum mechanics","level":1,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1080/08927022.2010.497926","doi":"https://doi.org/10.1080/08927022.2010.497926","is_oa":false,"landing_page_url":"https://doi.org/10.1080/08927022.2010.497926","pdf_url":null,"source":{"id":"https://openalex.org/S45504773","display_name":"Molecular Simulation","issn_l":"0892-7022","issn":["0892-7022","1026-7638","1029-0435"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","norway-1","poland-70","russia-white-list-1"],"host_organization":"https://openalex.org/P4310320547","host_organization_name":"Taylor & Francis","host_organization_lineage":["https://openalex.org/P4310320547","https://openalex.org/P4310320449"],"host_organization_lineage_names":["Taylor & Francis","Informa"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Molecular Simulation","raw_type":"journal-article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":24,"referenced_works":["https://openalex.org/W224340457","https://openalex.org/W568941435","https://openalex.org/W631327049","https://openalex.org/W1965918240","https://openalex.org/W1981670174","https://openalex.org/W1990707682","https://openalex.org/W1997914011","https://openalex.org/W2005729036","https://openalex.org/W2018598628","https://openalex.org/W2023271753","https://openalex.org/W2023307116","https://openalex.org/W2023355484","https://openalex.org/W2042059938","https://openalex.org/W2068697671","https://openalex.org/W2086957099","https://openalex.org/W2087957930","https://openalex.org/W2123209173","https://openalex.org/W2139916893","https://openalex.org/W2142067003","https://openalex.org/W2345797510","https://openalex.org/W2949487419","https://openalex.org/W2950306813","https://openalex.org/W4248407473","https://openalex.org/W4285719527"],"related_works":["https://openalex.org/W2722878882","https://openalex.org/W2058026086","https://openalex.org/W2030673025","https://openalex.org/W2064244146","https://openalex.org/W2082155154","https://openalex.org/W1981816664","https://openalex.org/W2006199688","https://openalex.org/W2018598628","https://openalex.org/W1993115550","https://openalex.org/W2081200405"],"abstract_inverted_index":{"In":[0],"order":[1],"to":[2,18,55],"find":[3],"the":[4,7,11,19,23,26,34,38,47,67,83,92,98,106,113,117,121,147,174,179,191,200],"susceptibility":[5],"of":[6,16,66,94,132,181,202],"amino-Claisen":[8,122,148,182],"rearrangement":[9,68,99,123],"and":[10,28,49,57,100,102,124,135,142,157],"next":[12],"proton":[13,50,84,107,125,192],"shift":[14,51,85,108,126,193],"reaction":[15,194],"N-allyl-N-arylamine":[17],"substituent":[20,79],"effects":[21],"in":[22,146],"para":[24],"position,":[25],"kinetic":[27],"thermodynamic":[29],"parameters":[30],"were":[31],"calculated":[32,43],"at":[33],"B3LYP":[35],"level":[36],"using":[37],"6-31G**":[39],"basis":[40],"set.":[41],"The":[42,63,128,151],"activation":[44,114],"energies":[45],"for":[46,82,97,105,112,120,140,190],"rearrangements":[48],"reactions":[52],"are":[53,72,138],"close":[54],"44.4":[56],"49.5":[58],"kcal":[59],"mol\u2212":[60],"1,":[61],"respectively.":[62,150],"transition":[64],"states":[65],"with":[69,77,163],"electron-donor":[70],"substituents":[71],"more":[73],"stable":[74],"than":[75,161],"those":[76],"electron-withdrawing":[78,197],"groups,":[80],"but":[81],"reaction,":[86],"this":[87],"situation":[88],"is":[89,159],"reversed":[90],"(with":[91],"exception":[93],"fluorine":[95,101],"atom":[96],"chlorine":[103],"atoms":[104],"reaction).":[109],"Negative":[110],"values":[111,131],"entropy":[115],"confirm":[116],"concerted":[118],"mechanism":[119],"reaction.":[127,203],"Hammett":[129,169,186],"\u03c1":[130,170,187],"\u2212":[133,136],"2.4172":[134],"1.7791":[137],"obtained":[139],"\u03c3p":[141,158],"\u03c3\u2212":[143,164],"(enhanced":[144,165],"sigma)":[145],"rearrangement,":[149],"correlation":[152],"between":[153],"log(k":[154],"X/k":[155],"H)":[156],"weaker":[160],"that":[162,173,196],"sigma).":[166],"A":[167,184],"negative":[168],"value":[171,188],"indicates":[172,195],"electron-donating":[175],"groups":[176,198],"slightly":[177],"increase":[178,199],"rate":[180,201],"rearrangement.":[183],"positive":[185],"(2.4921)":[189]},"counts_by_year":[{"year":2018,"cited_by_count":1},{"year":2013,"cited_by_count":1},{"year":2012,"cited_by_count":1}],"updated_date":"2026-10-30T12:39:25.321706","created_date":"2016-06-24T00:00:00"}