{"id":"https://openalex.org/W1964668126","doi":"https://doi.org/10.1002/(sici)1099-1395(199608)9:8<515::aid-poc816>3.0.co;2-5","title":"Reaction pathways for ambident aryloxide O- and C-nucleophiles in SNAr displacement versus Meisenheimer complex formation with picryl halides. Stereoelectronic effects on regioselectivity","display_name":"Reaction pathways for ambident aryloxide O- and C-nucleophiles in SNAr displacement versus Meisenheimer complex formation with picryl halides. Stereoelectronic effects on regioselectivity","publication_year":1996,"publication_date":"1996-08-01","ids":{"openalex":"https://openalex.org/W1964668126","doi":"https://doi.org/10.1002/(sici)1099-1395(199608)9:8<515::aid-poc816>3.0.co;2-5","mag":"1964668126"},"language":"en","primary_location":{"id":"doi:10.1002/(sici)1099-1395(199608)9:8<515::aid-poc816>3.0.co;2-5","doi":"https://doi.org/10.1002/(sici)1099-1395(199608)9:8<515::aid-poc816>3.0.co;2-5","is_oa":false,"landing_page_url":"https://doi.org/10.1002/(sici)1099-1395(199608)9:8<515::aid-poc816>3.0.co;2-5","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","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/A5038862912","display_name":"Richard A. Manderville","orcid":"https://orcid.org/0000-0003-4035-8093","observed_orcids":["https://orcid.org/0000-0003-4035-8093"]},"institutions":[{"id":"https://openalex.org/I47251452","display_name":"Wake Forest University","ror":"https://ror.org/0207ad724","country_code":"US","type":"education","lineage":["https://openalex.org/I47251452"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Richard A. Manderville","raw_affiliation_strings":["Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA","institution_ids":["https://openalex.org/I47251452"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5080580572","display_name":"Julian M. Dust","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Julian M. Dust","raw_affiliation_strings":["Department of Chemistry, Sir Wilfred Grenfell College, Corner Brook, Newfoundland, A2H 6P9, Canada"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Sir Wilfred Grenfell College, Corner Brook, Newfoundland, A2H 6P9, Canada","institution_ids":[]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5007594566","display_name":"Erwin Buncel","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I204722609","display_name":"Queen's University","ror":"https://ror.org/02y72wh86","country_code":"CA","type":"education","lineage":["https://openalex.org/I204722609"]}],"countries":["CA"],"is_corresponding":false,"raw_author_name":"Erwin Buncel","raw_affiliation_strings":["Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6, Canada","Dept. of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6, Canada","institution_ids":["https://openalex.org/I204722609"]},{"raw_affiliation_string":"Dept. of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada","institution_ids":["https://openalex.org/I204722609"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5038862912"],"corresponding_institution_ids":["https://openalex.org/I47251452"],"apc_list":{"value":3930,"currency":"USD","value_usd":3930},"apc_paid":null,"fwci":0.8626,"has_fulltext":false,"cited_by_count":14,"citation_normalized_percentile":{"value":0.6425644,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":95},"biblio":{"volume":"9","issue":"8","first_page":"515","last_page":"528"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12191","display_name":"Chemical Reaction Mechanisms","score":0.9897000193595886,"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":0.9897000193595886,"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":0.001500000013038516,"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/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.0012000000569969416,"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/meisenheimer-complexes","display_name":"Meisenheimer complexes","score":0.8299999833106995},{"id":"https://openalex.org/keywords/ambident-nucleophiles","display_name":"ambident nucleophiles","score":0.8859999775886536},{"id":"https://openalex.org/keywords/nucleophilic-aromatic-substitution","display_name":"nucleophilic aromatic substitution","score":0.8970000147819519},{"id":"https://openalex.org/keywords/regioselectivity","display_name":"regioselectivity","score":0.9490000009536743},{"id":"https://openalex.org/keywords/stereoelectronic-effects","display_name":"stereoelectronic effects","score":0.9319999814033508},{"id":"https://openalex.org/keywords/phenoxide","display_name":"phenoxide","score":0.5590000152587891},{"id":"https://openalex.org/keywords/nucleofugality","display_name":"nucleofugality","score":0.828000009059906},{"id":"https://openalex.org/keywords/steric-hindrance","display_name":"steric hindrance","score":0.777999997138977},{"id":"https://openalex.org/keywords/reaction-pathways","display_name":"reaction pathways","score":0.37599998712539673}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9858781099319458},{"id":"https://openalex.org/C59759590","wikidata":"https://www.wikidata.org/wiki/Q2275927","display_name":"Regioselectivity","level":3,"score":0.9211025238037109},{"id":"https://openalex.org/C178907741","wikidata":"https://www.wikidata.org/wiki/Q745930","display_name":"Nucleophile","level":3,"score":0.8272138833999634},{"id":"https://openalex.org/C171560689","wikidata":"https://www.wikidata.org/wiki/Q193086","display_name":"Halide","level":2,"score":0.7075244784355164},{"id":"https://openalex.org/C107551265","wikidata":"https://www.wikidata.org/wiki/Q1458245","display_name":"Displacement (psychology)","level":2,"score":0.5066340565681458},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.4342033267021179},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3974607586860657},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.19637715816497803},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.07224854826927185},{"id":"https://openalex.org/C542102704","wikidata":"https://www.wikidata.org/wiki/Q183257","display_name":"Psychotherapist","level":1,"score":0.0},{"id":"https://openalex.org/C15744967","wikidata":"https://www.wikidata.org/wiki/Q9418","display_name":"Psychology","level":0,"score":0.0}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1002/(sici)1099-1395(199608)9:8<515::aid-poc816>3.0.co;2-5","doi":"https://doi.org/10.1002/(sici)1099-1395(199608)9:8<515::aid-poc816>3.0.co;2-5","is_oa":false,"landing_page_url":"https://doi.org/10.1002/(sici)1099-1395(199608)9:8<515::aid-poc816>3.0.co;2-5","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"},{"id":"doi:10.1002/(sici)1099-1395(199608)9:8<515::aid-poc816>3.3.co;2-x","doi":"https://doi.org/10.1002/(sici)1099-1395(199608)9:8<515::aid-poc816>3.3.co;2-x","is_oa":false,"landing_page_url":"https://doi.org/10.1002/(sici)1099-1395(199608)9:8<515::aid-poc816>3.3.co;2-x","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":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":54,"referenced_works":["https://openalex.org/W254955988","https://openalex.org/W590254631","https://openalex.org/W607406955","https://openalex.org/W1005733302","https://openalex.org/W1011544408","https://openalex.org/W1504444587","https://openalex.org/W1553651521","https://openalex.org/W1965261022","https://openalex.org/W1976221647","https://openalex.org/W1979933198","https://openalex.org/W1995689598","https://openalex.org/W1996779761","https://openalex.org/W1999413117","https://openalex.org/W2001390666","https://openalex.org/W2001741728","https://openalex.org/W2009814010","https://openalex.org/W2011509030","https://openalex.org/W2016872059","https://openalex.org/W2019871532","https://openalex.org/W2025120209","https://openalex.org/W2025473365","https://openalex.org/W2029104611","https://openalex.org/W2030841140","https://openalex.org/W2031703691","https://openalex.org/W2031800233","https://openalex.org/W2034177798","https://openalex.org/W2045043464","https://openalex.org/W2046369762","https://openalex.org/W2050592599","https://openalex.org/W2051379185","https://openalex.org/W2054029531","https://openalex.org/W2054354427","https://openalex.org/W2069607377","https://openalex.org/W2072062437","https://openalex.org/W2084982278","https://openalex.org/W2086681230","https://openalex.org/W2087730251","https://openalex.org/W2092324910","https://openalex.org/W2092445792","https://openalex.org/W2107789026","https://openalex.org/W2108448270","https://openalex.org/W2111834585","https://openalex.org/W2313909178","https://openalex.org/W2327546552","https://openalex.org/W2330135322","https://openalex.org/W2943034305","https://openalex.org/W2949375447","https://openalex.org/W2950615386","https://openalex.org/W2950754651","https://openalex.org/W2951500919","https://openalex.org/W3004937382","https://openalex.org/W3005510352","https://openalex.org/W4232961182","https://openalex.org/W4253458668"],"related_works":["https://openalex.org/W2150584498","https://openalex.org/W4255439805","https://openalex.org/W2029104611","https://openalex.org/W2295803413","https://openalex.org/W1965261022","https://openalex.org/W2039264453","https://openalex.org/W1986216706","https://openalex.org/W1997837076","https://openalex.org/W3005510352","https://openalex.org/W2013971629"],"abstract_inverted_index":{"To":[0],"probe":[1],"regioselectivity":[2],"in":[3,34,41,108,141],"Meisenheimer":[4,98,152],"complexation,":[5],"the":[6,54,75,79,83,118,123,149,167,171,177,195,198,207,210],"reaction":[7],"of":[8,21,49,72,78,117,169,173,179,197,216],"two":[9],"picryl":[10,51,86,90,95,138,165],"halides":[11,52],"(PiX":[12],"where":[13,114],"X":[14,73,159],"=":[15,155,160],"F,":[16],"Cl)":[17],"with":[18,53,143,192],"a":[19],"series":[20],"aryloxide":[22,119],"nucleophiles":[23],"(phenoxide,":[24],"2,4,6-trimethylphenoxide":[25,64],"and":[26,40,63,93,158,213],"2,6-di-t-butylphenoxide)":[27],"were":[28],"monitored":[29],"by":[30,122,206,220],"1H":[31],"NMR":[32],"spectroscopy":[33],"dimethyl":[35],"sulphoxide":[36],"at":[37,43,101,134,145,209],"ambient":[38],"temperature":[39,45],"acetonitrile-dimethoxyethane(MeCN-DME)":[42],"low":[44],"(\u221240\u00b0C).":[46],"The":[47],"reactions":[48],"both":[50,164],"ambident":[55],"(oxygen":[56],"versus":[57],"carbon)":[58],"nucleophile,":[59],"phenoxide":[60],"ion":[61],"(PhO\u2212),":[62],"(mesitoxide,":[65],"MesO\u2212)":[66],"leads":[67],"to":[68,81,132,136,147,176,194,204],"clean":[69],"SNAr":[70],"displacement":[71],"via":[74],"oxygen":[76,115],"site":[77],"nucleophile":[80],"form":[82],"respective":[84,150],"aryl":[85],"ethers,":[87],"i.e.":[88],"phenyl":[89],"ether":[91,96],"(3a)":[92],"mesityl":[94],"(3b).":[97],"complex":[99],"formation":[100],"C-1":[102,135,174,217],"or":[103,183],"C-3":[104,146,180],"was":[105,130,185],"not":[106],"detected":[107],"these":[109],"systems.":[110],"With":[111],"2,-6-di-t-butylphenoxide":[112],"(2,6-DTBPhO\u2212),":[113],"attachment":[116,129],"is":[120],"precluded":[121],"bulky":[124],"ortho":[125],"t-butyl":[126],"groups,":[127],"para-carbon":[128],"found":[131],"occur":[133],"give":[137,148],"2,6-di-t-butylphenol":[139],"(3d)":[140],"competition":[142],"C-attack":[144],"carbon-bonded":[151],"complexes":[153],"[X":[154],"Cl":[156],"(4)":[157],"F":[161],"(5)].":[162],"For":[163],"halides,":[166],"ratio":[168],"3d,":[170],"product":[172,178],"attack,":[175,181],"4":[182],"5,":[184],"roughly":[186],"7:1.":[187],"These":[188],"findings":[189],"are":[190],"considered":[191],"regard":[193],"nucleofugality":[196],"halide,":[199],"X,":[200],"steric":[201],"hindrance":[202],"(F-strain)":[203],"attack":[205],"aryloxides":[208],"various":[211],"positions":[212],"stereoelectronic":[214],"stabilization":[215],"adducts":[218],"afforded":[219],"n":[221],"\u2192":[222],"\u03c3*":[223],"donation.":[224]},"counts_by_year":[{"year":2024,"cited_by_count":2},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2015,"cited_by_count":1},{"year":2014,"cited_by_count":1},{"year":2012,"cited_by_count":1}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}
