{"id":"https://openalex.org/W2006567571","doi":"https://doi.org/10.1021/ja038973x","title":"Basicity of Nucleophilic Carbenes in Aqueous and Nonaqueous SolventsTheoretical Predictions","display_name":"Basicity of Nucleophilic Carbenes in Aqueous and Nonaqueous SolventsTheoretical Predictions","publication_year":2004,"publication_date":"2004-06-22","ids":{"openalex":"https://openalex.org/W2006567571","doi":"https://doi.org/10.1021/ja038973x","mag":"2006567571","pmid":"https://pubmed.ncbi.nlm.nih.gov/15250724"},"language":"en","primary_location":{"id":"doi:10.1021/ja038973x","doi":"https://doi.org/10.1021/ja038973x","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja038973x","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","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":"Journal of the American Chemical Society","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"https://figshare.com/articles/journal_contribution/Basicity_of_Nucleophilic_Carbenes_in_Aqueous_and_Nonaqueous_Solvents_-_Theoretical_Predictions/22849379","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5056538180","display_name":"A.M. Magill","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I129801699","display_name":"University of Tasmania","ror":"https://ror.org/01nfmeh72","country_code":"AU","type":"education","lineage":["https://openalex.org/I129801699"]},{"id":"https://openalex.org/I79510175","display_name":"Cardiff University","ror":"https://ror.org/03kk7td41","country_code":"GB","type":"education","lineage":["https://openalex.org/I79510175"]}],"countries":["AU","GB"],"is_corresponding":false,"raw_author_name":"Alison M. Magill","raw_affiliation_strings":["Contribution from the School of Chemistry, University of Tasmania, Private Bag 75, Hobart, Tasmania, Australia 7001, and Department of Chemistry, Cardiff University, P.O. Box 912, Cardiff, U.K. CF10 3TB"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the School of Chemistry, University of Tasmania, Private Bag 75, Hobart, Tasmania, Australia 7001, and Department of Chemistry, Cardiff University, P.O. Box 912, Cardiff, U.K. CF10 3TB","institution_ids":["https://openalex.org/I129801699","https://openalex.org/I79510175"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5113218818","display_name":"K.J. Cavell","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I129801699","display_name":"University of Tasmania","ror":"https://ror.org/01nfmeh72","country_code":"AU","type":"education","lineage":["https://openalex.org/I129801699"]},{"id":"https://openalex.org/I79510175","display_name":"Cardiff University","ror":"https://ror.org/03kk7td41","country_code":"GB","type":"education","lineage":["https://openalex.org/I79510175"]}],"countries":["AU","GB"],"is_corresponding":false,"raw_author_name":"Kingsley J. Cavell","raw_affiliation_strings":["Contribution from the School of Chemistry, University of Tasmania, Private Bag 75, Hobart, Tasmania, Australia 7001, and Department of Chemistry, Cardiff University, P.O. Box 912, Cardiff, U.K. CF10 3TB"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the School of Chemistry, University of Tasmania, Private Bag 75, Hobart, Tasmania, Australia 7001, and Department of Chemistry, Cardiff University, P.O. Box 912, Cardiff, U.K. CF10 3TB","institution_ids":["https://openalex.org/I129801699","https://openalex.org/I79510175"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5052630690","display_name":"Brian F. Yates","orcid":"https://orcid.org/0000-0001-9663-3301","observed_orcids":["https://orcid.org/0000-0001-9663-3301"]},"institutions":[{"id":"https://openalex.org/I129801699","display_name":"University of Tasmania","ror":"https://ror.org/01nfmeh72","country_code":"AU","type":"education","lineage":["https://openalex.org/I129801699"]},{"id":"https://openalex.org/I79510175","display_name":"Cardiff University","ror":"https://ror.org/03kk7td41","country_code":"GB","type":"education","lineage":["https://openalex.org/I79510175"]}],"countries":["AU","GB"],"is_corresponding":false,"raw_author_name":"Brian F. Yates","raw_affiliation_strings":["Contribution from the School of Chemistry, University of Tasmania, Private Bag 75, Hobart, Tasmania, Australia 7001, and Department of Chemistry, Cardiff University, P.O. Box 912, Cardiff, U.K. CF10 3TB"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the School of Chemistry, University of Tasmania, Private Bag 75, Hobart, Tasmania, Australia 7001, and Department of Chemistry, Cardiff University, P.O. Box 912, Cardiff, U.K. CF10 3TB","institution_ids":["https://openalex.org/I129801699","https://openalex.org/I79510175"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":16.6032,"has_fulltext":false,"cited_by_count":461,"citation_normalized_percentile":{"value":0.99759047,"is_in_top_1_percent":true,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":97,"max":100},"biblio":{"volume":"126","issue":"28","first_page":"8717","last_page":"8724"},"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":0.5170999765396118,"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":0.5170999765396118,"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/T11790","display_name":"N-Heterocyclic Carbenes in Organic and Inorganic Chemistry","score":0.29440000653266907,"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/T10002","display_name":"Advanced Chemical Physics Studies","score":0.06870000064373016,"subfield":{"id":"https://openalex.org/subfields/3107","display_name":"Atomic and Molecular Physics, and Optics"},"field":{"id":"https://openalex.org/fields/31","display_name":"Physics and Astronomy"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/nucleophilic-carbenes","display_name":"nucleophilic carbenes","score":0.9980000257492065},{"id":"https://openalex.org/keywords/water-as-solvent","display_name":"water as solvent","score":0.7080000042915344},{"id":"https://openalex.org/keywords/nonaqueous-solvents","display_name":"non-aqueous solvents","score":0.8859999775886536},{"id":"https://openalex.org/keywords/dimethyl-sulfoxide","display_name":"dimethyl sulfoxide","score":0.972000002861023},{"id":"https://openalex.org/keywords/acetonitrile","display_name":"acetonitrile","score":0.9990000128746033},{"id":"https://openalex.org/keywords/water","display_name":"water","score":0.7379999756813049},{"id":"https://openalex.org/keywords/solvation-effects","display_name":"solvation effects","score":0.6129999756813049},{"id":"https://openalex.org/keywords/cbs-qb3","display_name":"CBS-QB3","score":0.8230000138282776}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9673148393630981},{"id":"https://openalex.org/C184651966","wikidata":"https://www.wikidata.org/wiki/Q906356","display_name":"Aqueous solution","level":2,"score":0.7733501195907593},{"id":"https://openalex.org/C148093993","wikidata":"https://www.wikidata.org/wiki/Q739398","display_name":"Solvation","level":3,"score":0.7561936974525452},{"id":"https://openalex.org/C2777463227","wikidata":"https://www.wikidata.org/wiki/Q408047","display_name":"Acetonitrile","level":2,"score":0.7530224323272705},{"id":"https://openalex.org/C178907741","wikidata":"https://www.wikidata.org/wiki/Q745930","display_name":"Nucleophile","level":3,"score":0.7275161147117615},{"id":"https://openalex.org/C2777164566","wikidata":"https://www.wikidata.org/wiki/Q419257","display_name":"Carbene","level":3,"score":0.6568453311920166},{"id":"https://openalex.org/C2778452553","wikidata":"https://www.wikidata.org/wiki/Q407927","display_name":"Dimethyl sulfoxide","level":2,"score":0.5252834558486938},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.4673265516757965},{"id":"https://openalex.org/C2910635913","wikidata":"https://www.wikidata.org/wiki/Q170167","display_name":"Trinitrotoluene","level":3,"score":0.4273698925971985},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.28623002767562866},{"id":"https://openalex.org/C147789679","wikidata":"https://www.wikidata.org/wiki/Q11372","display_name":"Physical chemistry","level":1,"score":0.27890655398368835},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2173110842704773},{"id":"https://openalex.org/C154238967","wikidata":"https://www.wikidata.org/wiki/Q12870","display_name":"Explosive material","level":2,"score":0.11911740899085999},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.054278045892715454}],"mesh":[],"locations_count":4,"locations":[{"id":"doi:10.1021/ja038973x","doi":"https://doi.org/10.1021/ja038973x","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja038973x","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","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":"Journal of the American Chemical Society","raw_type":"journal-article"},{"id":"pmid:15250724","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/15250724","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":"Journal of the American Chemical Society","raw_type":"Journal Article"},{"id":"pmh:oai:ecite.utas.edu.au:31988","doi":null,"is_oa":false,"landing_page_url":"http://ecite.utas.edu.au/31988","pdf_url":null,"source":{"id":"https://openalex.org/S4306401569","display_name":"eCite Digital Repository (University of Tasmania)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I129801699","host_organization_name":"University of Tasmania","host_organization_lineage":["https://openalex.org/I129801699"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"","raw_type":"Refereed Article"},{"id":"pmh:oai:figshare.com:article/22849379","doi":null,"is_oa":true,"landing_page_url":"https://figshare.com/articles/journal_contribution/Basicity_of_Nucleophilic_Carbenes_in_Aqueous_and_Nonaqueous_Solvents_-_Theoretical_Predictions/22849379","pdf_url":null,"source":{"id":"https://openalex.org/S4377196282","display_name":"Figshare","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I4210132348","host_organization_name":"Figshare (United Kingdom)","host_organization_lineage":["https://openalex.org/I4210132348"],"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":"","raw_type":"Text"}],"best_oa_location":{"id":"pmh:oai:figshare.com:article/22849379","doi":null,"is_oa":true,"landing_page_url":"https://figshare.com/articles/journal_contribution/Basicity_of_Nucleophilic_Carbenes_in_Aqueous_and_Nonaqueous_Solvents_-_Theoretical_Predictions/22849379","pdf_url":null,"source":{"id":"https://openalex.org/S4377196282","display_name":"Figshare","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I4210132348","host_organization_name":"Figshare (United Kingdom)","host_organization_lineage":["https://openalex.org/I4210132348"],"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":"","raw_type":"Text"},"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":46,"referenced_works":["https://openalex.org/W150677383","https://openalex.org/W1575072324","https://openalex.org/W1967010838","https://openalex.org/W1968884474","https://openalex.org/W1974796826","https://openalex.org/W1978500772","https://openalex.org/W1978537398","https://openalex.org/W1980061049","https://openalex.org/W2000207131","https://openalex.org/W2006470278","https://openalex.org/W2013052242","https://openalex.org/W2018760154","https://openalex.org/W2023834187","https://openalex.org/W2024045561","https://openalex.org/W2027435496","https://openalex.org/W2049044706","https://openalex.org/W2051305998","https://openalex.org/W2057358811","https://openalex.org/W2058848030","https://openalex.org/W2064188787","https://openalex.org/W2065663049","https://openalex.org/W2068956585","https://openalex.org/W2072682123","https://openalex.org/W2075541266","https://openalex.org/W2080793451","https://openalex.org/W2086505034","https://openalex.org/W2091431720","https://openalex.org/W2093001666","https://openalex.org/W2101627524","https://openalex.org/W2114743032","https://openalex.org/W2128951011","https://openalex.org/W2133627924","https://openalex.org/W2155604981","https://openalex.org/W2327110389","https://openalex.org/W2329847367","https://openalex.org/W2950885732","https://openalex.org/W2951059818","https://openalex.org/W2951564414","https://openalex.org/W2951987601","https://openalex.org/W2952293795","https://openalex.org/W3004933954","https://openalex.org/W3005510016","https://openalex.org/W4211172071","https://openalex.org/W4239400817","https://openalex.org/W4240524232","https://openalex.org/W4253609955"],"related_works":["https://openalex.org/W2001242533","https://openalex.org/W1984306804","https://openalex.org/W2150180544","https://openalex.org/W2890963736","https://openalex.org/W2028095501","https://openalex.org/W2808890226","https://openalex.org/W2161937681","https://openalex.org/W1971504526","https://openalex.org/W3001617896","https://openalex.org/W2372066207"],"abstract_inverted_index":{"The":[0],"complete":[1],"basis":[2],"set":[3],"method":[4],"CBS-QB3":[5],"was":[6,106],"used":[7,124],"in":[8,27,39,53,61,84],"conjunction":[9],"with":[10],"the":[11,18,54,109],"CPCM":[12],"solvation":[13],"model":[14],"to":[15,49,65,125],"predict":[16],"both":[17],"absolute":[19,36],"and":[20,33,72,94,103],"relative":[21],"pKa's":[22,88,105],"of":[23,56],"12":[24],"nucleophilic":[25],"carbenes":[26],"dimethyl":[28],"sulfoxide":[29],"(DMSO),":[30],"acetonitrile":[31],"(MeCN),":[32],"water.":[34],"Average":[35],"pKa":[37,78,129],"values":[38,60],"DMSO":[40],"ranged":[41],"from":[42],"14.4":[43],"+/-":[44,51,69,74,91,96],"0.16":[45,70],"for":[46,108],"3-methylthiazol-2-ylidene":[47],"(12)":[48,71,93],"27.9":[50],"0.23":[52],"case":[55],"bis(dimethylamino)carbene":[57],"(11),":[58],"while":[59],"MeCN":[62],"were":[63],"determined":[64],"be":[66,123],"between":[67,89,101],"25.7":[68],"39.1":[73],"0.25":[75],"(11).":[76,98],"Relative":[77],"calculations":[79],"yielded":[80],"similar":[81],"results.":[82],"Calculations":[83],"aqueous":[85],"solution":[86],"gave":[87],"21.2":[90],"0.2":[92],"34.0":[95],"0.3":[97],"Excellent":[99],"agreement":[100],"calculated":[102],"experimental":[104,113],"obtained":[107],"few":[110],"cases":[111],"where":[112],"numbers":[114],"are":[115],"available,":[116],"confirming":[117],"that":[118],"this":[119],"theoretical":[120],"approach":[121],"may":[122],"calculate":[126],"highly":[127],"accurate":[128],"values.":[130]},"counts_by_year":[{"year":2026,"cited_by_count":4},{"year":2025,"cited_by_count":8},{"year":2024,"cited_by_count":8},{"year":2023,"cited_by_count":7},{"year":2022,"cited_by_count":16},{"year":2021,"cited_by_count":13},{"year":2020,"cited_by_count":17},{"year":2019,"cited_by_count":17},{"year":2018,"cited_by_count":26},{"year":2017,"cited_by_count":23},{"year":2016,"cited_by_count":22},{"year":2015,"cited_by_count":24},{"year":2014,"cited_by_count":28},{"year":2013,"cited_by_count":35},{"year":2012,"cited_by_count":21}],"updated_date":"2026-11-07T11:25:07.637180","created_date":"2016-06-24T00:00:00"}