{"id":"https://openalex.org/W2793873301","doi":"https://doi.org/10.1002/poc.3829","title":"Superbase\u2010catalyzed domino 3H\u2010pyrroles synthesis from ketoximes and acetylene: DFT study vs experiment","display_name":"Superbase\u2010catalyzed domino 3H\u2010pyrroles synthesis from ketoximes and acetylene: DFT study vs experiment","publication_year":2018,"publication_date":"2018-02-27","ids":{"openalex":"https://openalex.org/W2793873301","doi":"https://doi.org/10.1002/poc.3829","mag":"2793873301"},"language":"en","primary_location":{"id":"doi:10.1002/poc.3829","doi":"https://doi.org/10.1002/poc.3829","is_oa":false,"landing_page_url":"https://doi.org/10.1002/poc.3829","pdf_url":null,"source":{"id":"https://openalex.org/S157344032","display_name":"Journal of Physical Organic Chemistry","issn_l":"0894-3230","issn":["0894-3230","1099-1395"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-1","ki-jl-1","norway-1","poland-40","russia-white-list-2"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Physical Organic Chemistry","raw_type":"journal-article"},"volume":null,"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/A5003248089","display_name":"Anton V. Kuzmin","orcid":"https://orcid.org/0000-0002-8114-6479","observed_orcids":["https://orcid.org/0000-0002-8114-6479"]},"institutions":[{"id":"https://openalex.org/I1313323035","display_name":"Russian Academy of Sciences","ror":"https://ror.org/05qrfxd25","country_code":"RU","type":"government","lineage":["https://openalex.org/I1313323035"]},{"id":"https://openalex.org/I4210098151","display_name":"A.E. Favorsky Irkutsk Institute of Chemistry","ror":"https://ror.org/00verxq29","country_code":"RU","type":"facility","lineage":["https://openalex.org/I1313323035","https://openalex.org/I4210098151","https://openalex.org/I4210145551"]},{"id":"https://openalex.org/I4210151983","display_name":"Limnological Institute","ror":"https://ror.org/04tfjah29","country_code":"RU","type":"facility","lineage":["https://openalex.org/I1313323035","https://openalex.org/I4210151983","https://openalex.org/I4210163714"]}],"countries":["RU"],"is_corresponding":false,"raw_author_name":"Anton V. Kuzmin","raw_affiliation_strings":["A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, Irkutsk, Russian Federation","Limnological Institute, Siberian Division of the Russian Academy of Sciences, Irkutsk, Russian Federation"],"raw_orcid":"https://orcid.org/0000-0002-8114-6479","affiliations":[{"raw_affiliation_string":"A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, Irkutsk, Russian Federation","institution_ids":["https://openalex.org/I1313323035","https://openalex.org/I4210098151"]},{"raw_affiliation_string":"Limnological Institute, Siberian Division of the Russian Academy of Sciences, Irkutsk, Russian Federation","institution_ids":["https://openalex.org/I1313323035","https://openalex.org/I4210151983"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5029805191","display_name":"Dmitrii A. Shabalin","orcid":"https://orcid.org/0000-0002-0685-9508","observed_orcids":["https://orcid.org/0000-0002-0685-9508"]},"institutions":[{"id":"https://openalex.org/I1313323035","display_name":"Russian Academy of Sciences","ror":"https://ror.org/05qrfxd25","country_code":"RU","type":"government","lineage":["https://openalex.org/I1313323035"]},{"id":"https://openalex.org/I4210098151","display_name":"A.E. Favorsky Irkutsk Institute of Chemistry","ror":"https://ror.org/00verxq29","country_code":"RU","type":"facility","lineage":["https://openalex.org/I1313323035","https://openalex.org/I4210098151","https://openalex.org/I4210145551"]}],"countries":["RU"],"is_corresponding":true,"raw_author_name":"Dmitrii A. Shabalin","raw_affiliation_strings":["A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, Irkutsk, Russian Federation"],"raw_orcid":"https://orcid.org/0000-0002-0685-9508","affiliations":[{"raw_affiliation_string":"A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, Irkutsk, Russian Federation","institution_ids":["https://openalex.org/I1313323035","https://openalex.org/I4210098151"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":3,"corresponding_author_ids":["https://openalex.org/A5029805191"],"corresponding_institution_ids":["https://openalex.org/I1313323035","https://openalex.org/I4210098151"],"apc_list":{"value":3930,"currency":"USD","value_usd":3930},"apc_paid":null,"fwci":0.2939,"has_fulltext":false,"cited_by_count":10,"citation_normalized_percentile":{"value":0.38546096,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":98},"biblio":{"volume":"31","issue":"6","first_page":null,"last_page":null},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12562","display_name":"Synthesis and Characterization of Pyrroles","score":0.8895999789237976,"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/T12562","display_name":"Synthesis and Characterization of Pyrroles","score":0.8895999789237976,"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/T12191","display_name":"Physical Organic Chemistry and Reaction Kinetics","score":0.08070000261068344,"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":0.006099999882280827,"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"}}],"keywords":[{"id":"https://openalex.org/keywords/cascade-reactions","display_name":"cascade reactions","score":0.7519999742507935},{"id":"https://openalex.org/keywords/ketoximes","display_name":"ketoximes","score":0.8259999752044678},{"id":"https://openalex.org/keywords/acetylene","display_name":"acetylene","score":0.9869999885559082},{"id":"https://openalex.org/keywords/superbases","display_name":"superbases","score":0.8769999742507935},{"id":"https://openalex.org/keywords/reaction-mechanism","display_name":"reaction mechanism","score":0.8569999933242798},{"id":"https://openalex.org/keywords/nucleophilic-addition","display_name":"nucleophilic addition","score":0.6650000214576721},{"id":"https://openalex.org/keywords/hydroxide-ion","display_name":"hydroxide ion","score":0.7200000286102295},{"id":"https://openalex.org/keywords/dft-calculations","display_name":"DFT calculations","score":0.4819999933242798}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9681267738342285},{"id":"https://openalex.org/C2778044633","wikidata":"https://www.wikidata.org/wiki/Q901690","display_name":"Superbase","level":3,"score":0.9636131525039673},{"id":"https://openalex.org/C2777517455","wikidata":"https://www.wikidata.org/wiki/Q133145","display_name":"Acetylene","level":2,"score":0.9156625270843506},{"id":"https://openalex.org/C2776416436","wikidata":"https://www.wikidata.org/wiki/Q3751781","display_name":"Domino","level":3,"score":0.8083287477493286},{"id":"https://openalex.org/C2776910235","wikidata":"https://www.wikidata.org/wiki/Q18574","display_name":"Reactivity (psychology)","level":3,"score":0.6585050225257874},{"id":"https://openalex.org/C178907741","wikidata":"https://www.wikidata.org/wiki/Q745930","display_name":"Nucleophile","level":3,"score":0.581384539604187},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.5548275709152222},{"id":"https://openalex.org/C20774148","wikidata":"https://www.wikidata.org/wiki/Q901669","display_name":"Nucleophilic addition","level":3,"score":0.515658974647522},{"id":"https://openalex.org/C140205800","wikidata":"https://www.wikidata.org/wiki/Q5860","display_name":"Carbon fibers","level":3,"score":0.496415913105011},{"id":"https://openalex.org/C2775896084","wikidata":"https://www.wikidata.org/wiki/Q425597","display_name":"Hydroxide","level":2,"score":0.4604973793029785},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.41861963272094727},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.39678627252578735},{"id":"https://openalex.org/C159985019","wikidata":"https://www.wikidata.org/wiki/Q181790","display_name":"Composite material","level":1,"score":0.0},{"id":"https://openalex.org/C104779481","wikidata":"https://www.wikidata.org/wiki/Q50707","display_name":"Composite number","level":2,"score":0.0},{"id":"https://openalex.org/C71924100","wikidata":"https://www.wikidata.org/wiki/Q11190","display_name":"Medicine","level":0,"score":0.0},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"score":0.0},{"id":"https://openalex.org/C204787440","wikidata":"https://www.wikidata.org/wiki/Q188504","display_name":"Alternative medicine","level":2,"score":0.0},{"id":"https://openalex.org/C142724271","wikidata":"https://www.wikidata.org/wiki/Q7208","display_name":"Pathology","level":1,"score":0.0}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1002/poc.3829","doi":"https://doi.org/10.1002/poc.3829","is_oa":false,"landing_page_url":"https://doi.org/10.1002/poc.3829","pdf_url":null,"source":{"id":"https://openalex.org/S157344032","display_name":"Journal of Physical Organic Chemistry","issn_l":"0894-3230","issn":["0894-3230","1099-1395"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-b","jufo-1","ki-jl-1","norway-1","poland-40","russia-white-list-2"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Physical Organic Chemistry","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":27,"referenced_works":["https://openalex.org/W28713913","https://openalex.org/W1527894967","https://openalex.org/W1902574066","https://openalex.org/W1992173555","https://openalex.org/W2012960809","https://openalex.org/W2013722101","https://openalex.org/W2017332513","https://openalex.org/W2018577705","https://openalex.org/W2037521703","https://openalex.org/W2060840627","https://openalex.org/W2061535637","https://openalex.org/W2079340916","https://openalex.org/W2082724839","https://openalex.org/W2143981217","https://openalex.org/W2148284063","https://openalex.org/W2157065376","https://openalex.org/W2344943240","https://openalex.org/W2398086939","https://openalex.org/W2409182773","https://openalex.org/W2482447882","https://openalex.org/W2494676700","https://openalex.org/W2509694353","https://openalex.org/W2745434683","https://openalex.org/W2950741211","https://openalex.org/W2952003978","https://openalex.org/W3085077543","https://openalex.org/W4388166534"],"related_works":["https://openalex.org/W2949943846","https://openalex.org/W1902574066","https://openalex.org/W2951448896","https://openalex.org/W2012180495","https://openalex.org/W4414108610","https://openalex.org/W2951160802","https://openalex.org/W1980640778","https://openalex.org/W3016226075","https://openalex.org/W2084340392","https://openalex.org/W2317761434"],"abstract_inverted_index":{"Abstract":[0],"Elimination":[1],"of":[2,10,14,28,36,42,58],"vinyl":[3],"alcohol":[4],"from":[5,18,39],"5\u2010vinyloxypyrrolines":[6],"in":[7,30],"the":[8],"presence":[9],"superbases":[11],"(final":[12],"step":[13],"domino":[15],"3H\u2010pyrroles":[16],"synthesis":[17],"ketoximes":[19],"and":[20],"acetylene)":[21],"is":[22,62],"studied":[23],"computationally":[24],"at":[25],"different":[26],"levels":[27],"theory":[29],"DMSO":[31],"solution":[32],"(PCM).":[33],"The":[34],"sequences":[35],"transformations":[37],"starting":[38],"nucleophilic":[40],"addition":[41],"hydroxide":[43],"ion":[44],"to":[45],"carbon\u2010carbon":[46],"or":[47],"carbon\u2010nitrogen":[48],"double":[49],"bonds":[50],"are":[51],"proposed":[52],"as":[53],"possible":[54],"mechanisms.":[55,66],"Unusual":[56],"reactivity":[57],"2,5\u2010dimethylphenyl":[59],"substituted":[60],"5\u2010vinyloxypyrroline":[61],"explained":[63],"within":[64],"these":[65]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2023,"cited_by_count":6},{"year":2020,"cited_by_count":2},{"year":2019,"cited_by_count":1}],"updated_date":"2026-10-30T12:39:25.321706","created_date":"2018-03-29T00:00:00"}