{"id":"https://openalex.org/W2031689350","doi":"https://doi.org/10.1021/jo990509g","title":"Transition Structure Geometries for Transfers of Neutral and Anionic Nitrogen to Lithiated Carbanions","display_name":"Transition Structure Geometries for Transfers of Neutral and Anionic Nitrogen to Lithiated Carbanions","publication_year":1999,"publication_date":"1999-06-24","ids":{"openalex":"https://openalex.org/W2031689350","doi":"https://doi.org/10.1021/jo990509g","mag":"2031689350","pmid":"https://pubmed.ncbi.nlm.nih.gov/34237839"},"language":"en","primary_location":{"id":"doi:10.1021/jo990509g","doi":"https://doi.org/10.1021/jo990509g","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo990509g","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"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/A5072926516","display_name":"Peter Andrew Beak","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I157725225","display_name":"University of Illinois Urbana-Champaign","ror":"https://ror.org/047426m28","country_code":"US","type":"education","lineage":["https://openalex.org/I157725225"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Peter Beak","raw_affiliation_strings":["Department of Chemistry, University of Illinois, Urbana, Illinois 61801"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Illinois, Urbana, Illinois 61801","institution_ids":["https://openalex.org/I157725225"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5034508205","display_name":"Kathryn Rose Conser","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I157725225","display_name":"University of Illinois Urbana-Champaign","ror":"https://ror.org/047426m28","country_code":"US","type":"education","lineage":["https://openalex.org/I157725225"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Kathryn Conser Basu","raw_affiliation_strings":["Department of Chemistry, University of Illinois, Urbana, Illinois 61801"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Illinois, Urbana, Illinois 61801","institution_ids":["https://openalex.org/I157725225"]}]},{"author_position":"last","author":{"id":null,"display_name":"James J. Li","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I157725225","display_name":"University of Illinois Urbana-Champaign","ror":"https://ror.org/047426m28","country_code":"US","type":"education","lineage":["https://openalex.org/I157725225"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"James J. Li","raw_affiliation_strings":["Department of Chemistry, University of Illinois, Urbana, Illinois 61801"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Illinois, Urbana, Illinois 61801","institution_ids":["https://openalex.org/I157725225"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I157725225"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":0.6138,"has_fulltext":false,"cited_by_count":10,"citation_normalized_percentile":{"value":0.62414819,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":94},"biblio":{"volume":"64","issue":"14","first_page":"5218","last_page":"5223"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12228","display_name":"Coordination Chemistry and Organometallics","score":0.7939000129699707,"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/T12228","display_name":"Coordination Chemistry and Organometallics","score":0.7939000129699707,"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":"Chemical Reaction Mechanisms","score":0.19179999828338623,"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/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.006599999964237213,"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/nitrogen-transfer","display_name":"nitrogen transfer","score":0.6039999723434448},{"id":"https://openalex.org/keywords/nucleophilic-substitution","display_name":"nucleophilic substitution","score":0.7649999856948853},{"id":"https://openalex.org/keywords/transition-state-structure","display_name":"transition state structure","score":0.6700000166893005},{"id":"https://openalex.org/keywords/organolithium-reagents","display_name":"organolithium reagents","score":0.8259999752044678},{"id":"https://openalex.org/keywords/isotopic-scrambling","display_name":"isotopic scrambling","score":0.8339999914169312},{"id":"https://openalex.org/keywords/amination","display_name":"amination","score":0.4869999885559082},{"id":"https://openalex.org/keywords/substituent-effects","display_name":"substituent effects","score":0.5609999895095825}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9434494376182556},{"id":"https://openalex.org/C82894169","wikidata":"https://www.wikidata.org/wiki/Q898552","display_name":"Carbanion","level":2,"score":0.8947641849517822},{"id":"https://openalex.org/C40875361","wikidata":"https://www.wikidata.org/wiki/Q2356542","display_name":"Reagent","level":2,"score":0.7563890218734741},{"id":"https://openalex.org/C111592845","wikidata":"https://www.wikidata.org/wiki/Q2867924","display_name":"Trigonal bipyramidal molecular geometry","level":3,"score":0.6557800769805908},{"id":"https://openalex.org/C178907741","wikidata":"https://www.wikidata.org/wiki/Q745930","display_name":"Nucleophile","level":3,"score":0.6387479305267334},{"id":"https://openalex.org/C2778651986","wikidata":"https://www.wikidata.org/wiki/Q2515180","display_name":"Butyllithium","level":2,"score":0.627149224281311},{"id":"https://openalex.org/C537208039","wikidata":"https://www.wikidata.org/wiki/Q627","display_name":"Nitrogen","level":2,"score":0.6141079068183899},{"id":"https://openalex.org/C75079739","wikidata":"https://www.wikidata.org/wiki/Q1571801","display_name":"Intramolecular force","level":2,"score":0.5937233567237854},{"id":"https://openalex.org/C135731615","wikidata":"https://www.wikidata.org/wiki/Q658656","display_name":"Nucleophilic substitution","level":2,"score":0.5685833096504211},{"id":"https://openalex.org/C111185830","wikidata":"https://www.wikidata.org/wiki/Q503396","display_name":"Substitution reaction","level":2,"score":0.49012264609336853},{"id":"https://openalex.org/C140205800","wikidata":"https://www.wikidata.org/wiki/Q5860","display_name":"Carbon fibers","level":3,"score":0.42702916264533997},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.39736804366111755},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.35011059045791626},{"id":"https://openalex.org/C188027245","wikidata":"https://www.wikidata.org/wiki/Q750446","display_name":"Polymer chemistry","level":1,"score":0.3358507752418518},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.19358831644058228},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.14761504530906677},{"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/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}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1021/jo990509g","doi":"https://doi.org/10.1021/jo990509g","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jo990509g","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of Organic Chemistry","raw_type":"journal-article"},{"id":"pmid:34237839","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/34237839","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"The Journal of 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":16,"referenced_works":["https://openalex.org/W1965115830","https://openalex.org/W1975710523","https://openalex.org/W1982606817","https://openalex.org/W1983340773","https://openalex.org/W1992658247","https://openalex.org/W2002256833","https://openalex.org/W2035854929","https://openalex.org/W2075014224","https://openalex.org/W2076540524","https://openalex.org/W2077396966","https://openalex.org/W2117959544","https://openalex.org/W2323658292","https://openalex.org/W2329988767","https://openalex.org/W2950158176","https://openalex.org/W2952917240","https://openalex.org/W4250052852"],"related_works":["https://openalex.org/W2078491512","https://openalex.org/W1975710523","https://openalex.org/W2775705640","https://openalex.org/W2060371594","https://openalex.org/W2950549259","https://openalex.org/W2136092988","https://openalex.org/W2078195746","https://openalex.org/W2758023404","https://openalex.org/W1981354384","https://openalex.org/W1965571341"],"abstract_inverted_index":{"The":[0,16],"geometries":[1],"of":[2,18,22,43,46,71,83,111,123,139],"nucleophilic":[3,137],"substitutions":[4],"at":[5,108,143],"neutral":[6,144],"and":[7,77,88,97,115,145],"anionic":[8,73,146],"nitrogen":[9,39,52,74,122],"by":[10,141],"organolithium":[11,113],"species":[12],"have":[13],"been":[14],"investigated.":[15],"demonstration":[17],"an":[19,27,61],"intramolecular":[20],"conversion":[21],"9":[23],"to":[24,56,120],"10":[25],"provides":[26],"endocyclic":[28,66],"restriction":[29,67],"test":[30],"which":[31],"supports":[32],"a":[33],"trigonal":[34,132],"bipyramidal":[35,133],"transition":[36,134],"structure":[37],"for":[38,69,136],"transfer.":[40],"A":[41],"lack":[42],"isotopic":[44],"scrambling":[45],"12a":[47],"-":[48],"18":[49],"O":[50],"during":[51],"transfer":[53],"is":[54],"taken":[55],"rule":[57],"out":[58],"reaction":[59],"via":[60],"oriented":[62],"ion":[63],"pair.":[64],"Attempted":[65],"tests":[68],"transfers":[70],"formally":[72],"with":[75,92,105,116,131],"32":[76],"33":[78],"were":[79],"not":[80],"successful.":[81],"Reactions":[82],"n":[84],"-butyl,":[85],"s":[86],"-butyl":[87],"tert":[89],"-butyllithium":[90],"reagents":[91],"16,":[93],"23,":[94],"30,":[95],"31,":[96],"36":[98],"\u2212":[99],"38":[100],"generally":[101],"afford":[102],"higher":[103],"yields":[104],"increasing":[106],"substitution":[107,118],"the":[109,112,121,124],"carbon":[110,142],"reagent":[114],"decreasing":[117],"adjacent":[119],"aminating":[125],"reagent.":[126],"These":[127],"results":[128],"are":[129],"consistent":[130],"states":[135],"displacements":[138],"oxygen":[140],"nitrogen.":[147]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2018,"cited_by_count":1},{"year":2015,"cited_by_count":1}],"updated_date":"2026-10-30T12:39:25.321706","created_date":"2016-06-24T00:00:00"}
