{"id":"https://openalex.org/W4297348011","doi":"https://doi.org/10.3390/computation10100172","title":"Solvent Effects in the Regioselective N-Functionalization of Tautomerizable Heterocycles Catalyzed by Methyl Trifluoromethanesulfonate: A Density Functional Theory Study with Implicit Solvent Model","display_name":"Solvent Effects in the Regioselective N-Functionalization of Tautomerizable Heterocycles Catalyzed by Methyl Trifluoromethanesulfonate: A Density Functional Theory Study with Implicit Solvent Model","publication_year":2022,"publication_date":"2022-09-26","ids":{"openalex":"https://openalex.org/W4297348011","doi":"https://doi.org/10.3390/computation10100172"},"language":"en","primary_location":{"id":"doi:10.3390/computation10100172","is_oa":true,"landing_page_url":"https://doi.org/10.3390/computation10100172","pdf_url":"https://www.mdpi.com/2079-3197/10/10/172/pdf?version=1665986525","source":{"id":"https://openalex.org/S2738402919","display_name":"Computation","issn_l":"2079-3197","issn":["2079-3197"],"is_oa":true,"is_in_doaj":true,"is_core":true,"host_organization":"https://openalex.org/P4310310987","host_organization_name":"Multidisciplinary Digital Publishing Institute","host_organization_lineage":["https://openalex.org/P4310310987"],"host_organization_lineage_names":["Multidisciplinary Digital Publishing Institute"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Computation","raw_type":"journal-article"},"type":"article","indexed_in":["crossref","doaj"],"open_access":{"is_oa":true,"oa_status":"gold","oa_url":"https://www.mdpi.com/2079-3197/10/10/172/pdf?version=1665986525","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5044193191","display_name":"Nelson H. Morgon","orcid":"https://orcid.org/0000-0002-8349-8179"},"institutions":[{"id":"https://openalex.org/I181391015","display_name":"Universidade Estadual de Campinas (UNICAMP)","ror":"https://ror.org/04wffgt70","country_code":"BR","type":"education","lineage":["https://openalex.org/I181391015"]}],"countries":["BR"],"is_corresponding":false,"raw_author_name":"Nelson H. Morgon","raw_affiliation_strings":["Department of Physical Chemistry, Institute of Chemistry, Campinas State University, Campinas 13083-970, S\u00e3o Paulo, Brazil"],"affiliations":[{"raw_affiliation_string":"Department of Physical Chemistry, Institute of Chemistry, Campinas State University, Campinas 13083-970, S\u00e3o Paulo, Brazil","institution_ids":["https://openalex.org/I181391015"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5073882752","display_name":"Srijit Biswas","orcid":"https://orcid.org/0000-0003-2363-7381"},"institutions":[{"id":"https://openalex.org/I106542073","display_name":"University of Calcutta","ror":"https://ror.org/01e7v7w47","country_code":"IN","type":"education","lineage":["https://openalex.org/I106542073"]}],"countries":["IN"],"is_corresponding":false,"raw_author_name":"Srijit Biswas","raw_affiliation_strings":["Department of Chemistry, University of Calcuta, 92, A.P.C. Road, Kolkata 700 009, West Bengal, India"],"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Calcuta, 92, A.P.C. Road, Kolkata 700 009, West Bengal, India","institution_ids":["https://openalex.org/I106542073"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5046059134","display_name":"Surajit Duari","orcid":"https://orcid.org/0000-0002-3345-0353"},"institutions":[{"id":"https://openalex.org/I106542073","display_name":"University of Calcutta","ror":"https://ror.org/01e7v7w47","country_code":"IN","type":"education","lineage":["https://openalex.org/I106542073"]}],"countries":["IN"],"is_corresponding":false,"raw_author_name":"Surajit Duari","raw_affiliation_strings":["Department of Chemistry, University of Calcuta, 92, A.P.C. Road, Kolkata 700 009, West Bengal, India"],"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Calcuta, 92, A.P.C. Road, Kolkata 700 009, West Bengal, India","institution_ids":["https://openalex.org/I106542073"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5074135352","display_name":"Aguinaldo Robinson de Souza","orcid":"https://orcid.org/0000-0003-2373-267X"},"institutions":[{"id":"https://openalex.org/I879563668","display_name":"Universidade Estadual Paulista (Unesp)","ror":"https://ror.org/00987cb86","country_code":"BR","type":"education","lineage":["https://openalex.org/I879563668"]}],"countries":["BR"],"is_corresponding":true,"raw_author_name":"Aguinaldo R. de Souza","raw_affiliation_strings":["Department of Chemistry, School of Science, S\u00e3o Paulo State University, Bauru 17033-360, S\u00e3o Paulo, Brazil"],"affiliations":[{"raw_affiliation_string":"Department of Chemistry, School of Science, S\u00e3o Paulo State University, Bauru 17033-360, S\u00e3o Paulo, Brazil","institution_ids":["https://openalex.org/I879563668"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":4,"corresponding_author_ids":["https://openalex.org/A5074135352"],"corresponding_institution_ids":["https://openalex.org/I879563668"],"apc_list":{"value":1400,"currency":"CHF","value_usd":1515},"apc_paid":{"value":1400,"currency":"CHF","value_usd":1515},"fwci":0.1087,"has_fulltext":false,"cited_by_count":2,"citation_normalized_percentile":{"value":0.40214401,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":99},"biblio":{"volume":"10","issue":"10","first_page":"172","last_page":"172"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12191","display_name":"Chemical Reaction Mechanisms","score":0.9998000264167786,"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":"Chemical Reaction Mechanisms","score":0.9998000264167786,"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":0.9995999932289124,"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/T13208","display_name":"Synthesis of heterocyclic compounds","score":0.9990000128746033,"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/chemistry","display_name":"Chemistry","score":0.7477233409881592},{"id":"https://openalex.org/keywords/density-functional-theory","display_name":"Density functional theory","score":0.5721880197525024},{"id":"https://openalex.org/keywords/computational-chemistry","display_name":"Computational chemistry","score":0.5349975824356079},{"id":"https://openalex.org/keywords/solvent-effects","display_name":"Solvent effects","score":0.4838949143886566},{"id":"https://openalex.org/keywords/solvent","display_name":"Solvent","score":0.4562254548072815},{"id":"https://openalex.org/keywords/acetonitrile","display_name":"Acetonitrile","score":0.4500282108783722},{"id":"https://openalex.org/keywords/yield","display_name":"Yield (engineering)","score":0.4448786973953247},{"id":"https://openalex.org/keywords/physical-chemistry","display_name":"Physical chemistry","score":0.4355493485927582},{"id":"https://openalex.org/keywords/sn2-reaction","display_name":"SN2 reaction","score":0.41965237259864807},{"id":"https://openalex.org/keywords/thermodynamics","display_name":"Thermodynamics","score":0.3597396910190582},{"id":"https://openalex.org/keywords/organic-chemistry","display_name":"Organic chemistry","score":0.2616272568702698}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7477233409881592},{"id":"https://openalex.org/C152365726","wikidata":"https://www.wikidata.org/wiki/Q1048589","display_name":"Density functional theory","level":2,"score":0.5721880197525024},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.5349975824356079},{"id":"https://openalex.org/C132439834","wikidata":"https://www.wikidata.org/wiki/Q7559035","display_name":"Solvent effects","level":3,"score":0.4838949143886566},{"id":"https://openalex.org/C2780471494","wikidata":"https://www.wikidata.org/wiki/Q146505","display_name":"Solvent","level":2,"score":0.4562254548072815},{"id":"https://openalex.org/C2777463227","wikidata":"https://www.wikidata.org/wiki/Q408047","display_name":"Acetonitrile","level":2,"score":0.4500282108783722},{"id":"https://openalex.org/C134121241","wikidata":"https://www.wikidata.org/wiki/Q899301","display_name":"Yield (engineering)","level":2,"score":0.4448786973953247},{"id":"https://openalex.org/C147789679","wikidata":"https://www.wikidata.org/wiki/Q11372","display_name":"Physical chemistry","level":1,"score":0.4355493485927582},{"id":"https://openalex.org/C96765332","wikidata":"https://www.wikidata.org/wiki/Q838084","display_name":"SN2 reaction","level":2,"score":0.41965237259864807},{"id":"https://openalex.org/C97355855","wikidata":"https://www.wikidata.org/wiki/Q11473","display_name":"Thermodynamics","level":1,"score":0.3597396910190582},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2616272568702698},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0}],"mesh":[],"locations_count":5,"locations":[{"id":"doi:10.3390/computation10100172","is_oa":true,"landing_page_url":"https://doi.org/10.3390/computation10100172","pdf_url":"https://www.mdpi.com/2079-3197/10/10/172/pdf?version=1665986525","source":{"id":"https://openalex.org/S2738402919","display_name":"Computation","issn_l":"2079-3197","issn":["2079-3197"],"is_oa":true,"is_in_doaj":true,"is_core":true,"host_organization":"https://openalex.org/P4310310987","host_organization_name":"Multidisciplinary Digital Publishing Institute","host_organization_lineage":["https://openalex.org/P4310310987"],"host_organization_lineage_names":["Multidisciplinary Digital Publishing Institute"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Computation","raw_type":"journal-article"},{"id":"pmh:oai:doaj.org/article:83e12ea213fd4b8b827345c06d6c0a93","is_oa":true,"landing_page_url":"https://doaj.org/article/83e12ea213fd4b8b827345c06d6c0a93","pdf_url":null,"source":{"id":"https://openalex.org/S112646816","display_name":"SHILAP Revista de lepidopterolog\u00eda","issn_l":"0300-5267","issn":["0300-5267","2340-4078"],"is_oa":true,"is_in_doaj":true,"is_core":false,"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"Computation, Vol 10, Iss 10, p 172 (2022)","raw_type":"article"},{"id":"pmh:oai:https://www.repositorio.unicamp.br/:1257280","is_oa":true,"landing_page_url":"https://hdl.handle.net/20.500.12733/6901","pdf_url":null,"source":{"id":"https://openalex.org/S4306402641","display_name":"LA Referencia (Red Federada de Repositorios Institucionales de Publicaciones Cient\u00edficas)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"host_organization":"https://openalex.org/I4383465926","host_organization_name":"LA Referencia","host_organization_lineage":["https://openalex.org/I4383465926"],"host_organization_lineage_names":[],"type":"repository"},"license":"other-oa","license_id":"https://openalex.org/licenses/other-oa","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"reponame:Reposit\u00f3rio da Produ\u00e7\u00e3o Cient\u00edfica e Intelectual da Unicamp","raw_type":"info:eu-repo/semantics/publishedVersion"},{"id":"pmh:oai:mdpi.com:/2079-3197/10/10/172/","is_oa":true,"landing_page_url":"https://dx.doi.org/10.3390/computation10100172","pdf_url":null,"source":{"id":"https://openalex.org/S4306400947","display_name":"MDPI (MDPI AG)","issn_l":null,"issn":null,"is_oa":true,"is_in_doaj":false,"is_core":false,"host_organization":"https://openalex.org/I4210097602","host_organization_name":"Multidisciplinary Digital Publishing Institute (Switzerland)","host_organization_lineage":["https://openalex.org/I4210097602"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"Computation; Volume 10; Issue 10; Pages: 172","raw_type":"Text"},{"id":"pmh:oai:repositorio.unesp.br:11449/246157","is_oa":true,"landing_page_url":"http://doi.org/10.3390/computation10100172","pdf_url":null,"source":{"id":"https://openalex.org/S4306402641","display_name":"LA Referencia (Red Federada de Repositorios Institucionales de Publicaciones Cient\u00edficas)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"host_organization":"https://openalex.org/I4383465926","host_organization_name":"LA Referencia","host_organization_lineage":["https://openalex.org/I4383465926"],"host_organization_lineage_names":[],"type":"repository"},"license":"other-oa","license_id":"https://openalex.org/licenses/other-oa","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"instacron:UNESP","raw_type":"info:eu-repo/semantics/article"}],"best_oa_location":{"id":"doi:10.3390/computation10100172","is_oa":true,"landing_page_url":"https://doi.org/10.3390/computation10100172","pdf_url":"https://www.mdpi.com/2079-3197/10/10/172/pdf?version=1665986525","source":{"id":"https://openalex.org/S2738402919","display_name":"Computation","issn_l":"2079-3197","issn":["2079-3197"],"is_oa":true,"is_in_doaj":true,"is_core":true,"host_organization":"https://openalex.org/P4310310987","host_organization_name":"Multidisciplinary Digital Publishing Institute","host_organization_lineage":["https://openalex.org/P4310310987"],"host_organization_lineage_names":["Multidisciplinary Digital Publishing Institute"],"type":"journal"},"license":"cc-by","license_id":"https://openalex.org/licenses/cc-by","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Computation","raw_type":"journal-article"},"sustainable_development_goals":[{"display_name":"Affordable and clean energy","score":0.8199999928474426,"id":"https://metadata.un.org/sdg/7"}],"awards":[],"funders":[],"has_content":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W4297348011.pdf","grobid_xml":"https://content.openalex.org/works/W4297348011.grobid-xml"},"referenced_works_count":19,"referenced_works":["https://openalex.org/W1992173555","https://openalex.org/W2008708918","https://openalex.org/W2011215428","https://openalex.org/W2063815699","https://openalex.org/W2079473982","https://openalex.org/W2085837863","https://openalex.org/W2143981217","https://openalex.org/W2159687093","https://openalex.org/W2315008638","https://openalex.org/W2528714149","https://openalex.org/W3004465863","https://openalex.org/W3013434462","https://openalex.org/W3112269985","https://openalex.org/W4206652486","https://openalex.org/W4213008413","https://openalex.org/W4214632039","https://openalex.org/W4231649355","https://openalex.org/W4282944441","https://openalex.org/W4293079631"],"related_works":["https://openalex.org/W1985832542","https://openalex.org/W2032892660","https://openalex.org/W2091559720","https://openalex.org/W2808434441","https://openalex.org/W2369886796","https://openalex.org/W3013434462","https://openalex.org/W1966788970","https://openalex.org/W2126474843","https://openalex.org/W2324603767","https://openalex.org/W2806854034"],"abstract_inverted_index":{"Methyl":[0],"trifluoromethanesulfonate":[1],"was":[2,54,67,86,117,159],"found":[3,68],"to":[4,23,32,69,105,125,145],"catalyze":[5],"the":[6,9,13,49,52,59,65,84,107,127,131,139,162,174],"reaction":[7,60,85,149],"of":[8,12,16,45,51,58,64,83,157,173],"nucleophilic":[10],"substitution":[11],"hydroxyl":[14],"group":[15,26],"alcohols":[17],"by":[18,21],"N-heterocycles":[19],"followed":[20],"X-":[22],"N-":[24],"alkyl":[25],"migration":[27],"(X":[28],"=":[29],"O,":[30],"S)":[31],"obtain":[33],"N-functionalized":[34],"benzoxazolone,":[35],"benzothiazolethione,":[36],"indoline,":[37],"benzoimidazolethione":[38],"and":[39,73,78,98,119,188],"pyridinone":[40],"derivatives.":[41],"A":[42],"high":[43],"degree":[44],"solvent":[46,189],"dependency":[47],"on":[48,130,166],"yield":[50,63],"products":[53],"observed":[55],"during":[56],"optimization":[57],"parameters.":[61],"The":[62,81,95,155,169],"product":[66],"be":[70],"0%,":[71],"48%":[72],"70%":[74],"in":[75],"acetonitrile,":[76],"1,2-dichloroethane":[77],"chloroform,":[79],"respectively.":[80],"mechanism":[82],"established":[87],"through":[88],"experiments":[89],"as":[90,92],"well":[91],"DFT":[93],"calculations.":[94],"functional":[96],"B3LYP":[97],"6-311++G(d)":[99],"basis":[100],"function":[101],"sets":[102],"were":[103,123,142,153,176],"used":[104],"optimize":[106],"molecular":[108],"geometries.":[109],"D3":[110],"Grimme":[111],"empiric":[112],"dispersion":[113],"with":[114,178],"Becke\u2013Johnson":[115],"dumping":[116],"employed,":[118],"harmonic":[120],"vibrational":[121,179,182],"frequencies":[122],"calculated":[124],"characterize":[126],"stationary":[128,140],"points":[129,141],"potential":[132],"energy":[133,171,183],"surface.":[134],"To":[135],"ensure":[136],"that":[137],"all":[138],"smoothly":[143],"connected":[144],"each":[146],"other,":[147],"intrinsic":[148],"coordinate":[150],"(IRC)":[151],"analyses":[152],"performed.":[154],"influence":[156],"solvents":[158],"considered":[160],"using":[161],"solvation":[163],"model":[164],"based":[165],"density":[167],"(SMD).":[168],"free":[170],"profiles":[172],"mechanisms":[175],"obtained":[177],"unscaled":[180],"zero-point":[181],"(ZPE),":[184],"thermal,":[185],"enthalpy,":[186],"entropic":[187],"corrections.":[190]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2022,"cited_by_count":1}],"updated_date":"2025-11-06T03:46:38.306776","created_date":"2025-10-10T00:00:00"}