{"doi":"10.1002/poc.1325","title":"Do general nucleophilicity scales exist?","abstract":"<jats:title>Abstract</jats:title><jats:p>Comprehensive nucleophilicity scales including <jats:italic>π</jats:italic>‐, <jats:italic>n</jats:italic>‐ and <jats:italic>σ</jats:italic>‐nucleophiles have been constructed using benzhydrylium ions and structurally related quinone methides as reference electrophiles. It is shown how the correlation (Eqn (1)) log <jats:italic>k</jats:italic><jats:sub>20°C</jats:sub> = <jats:italic>s</jats:italic>(<jats:italic>E</jats:italic> <jats:italic>+</jats:italic> <jats:italic>N</jats:italic>), where <jats:italic>s</jats:italic> and <jats:italic>N</jats:italic> are nucleophile‐specific parameters and <jats:italic>E</jats:italic> is an electrophile‐specific parameter, has recently been employed to characterize further classes of nucleophiles (phosphines, amines, isonitriles, trifluoromethanesulfonyl‐substituted carbanions) and electrophiles (2‐benzylideneindan‐1,3‐diones and benzylidenebarbituric acids). Practical applications of the reactivity parameters <jats:italic>E</jats:italic>, <jats:italic>N</jats:italic> and <jats:italic>s</jats:italic> for developing Friedel–Crafts alkylations in neutral alcoholic or aqueous solution and for characterizing nucleophilic organocatalysts will be discussed. Eventually, a new correlation equation will be presented, which includes Eqn (1), the Ritchie equation (nucleophilic additions to stabilized carbocations), and the Swain–Scott equation (nucleophilic substitutions of methyl halides) as special cases. Copyright © 2008 John Wiley &amp; Sons, Ltd.</jats:p>","journal":"Journal of Physical Organic Chemistry","year":2008,"id":441481,"datarank":9.674810065748325,"base_score":5.823045895483019,"endowment":5.823045895483019,"self_citation_contribution":0.8734568843224529,"citation_network_contribution":8.801353181425872,"self_endowment_contribution":0.8734568843224529,"citer_contribution":8.801353181425872,"corpus_percentile":null,"corpus_rank":null,"citation_count":337,"citer_count":200,"citers_with_citation_signal":200,"citers_with_endowment":200,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":203005,"name":"Armin R. Ofial","orcid":"0000-0002-9600-2793","position":1,"is_corresponding":false},{"id":217599,"name":"Herbert Mayr","orcid":"0000-0003-0768-5199","position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Do general nucleophilicity scales exist?","abstract":"<jats:title>Abstract</jats:title><jats:p>Comprehensive nucleophilicity scales including <jats:italic>π</jats:italic>‐, <jats:italic>n</jats:italic>‐ and <jats:italic>σ</jats:italic>‐nucleophiles have been constructed using benzhydrylium ions and structurally related quinone methides as reference electrophiles. It is shown how the correlation (Eqn (1)) log <jats:italic>k</jats:italic><jats:sub>20°C</jats:sub> = <jats:italic>s</jats:italic>(<jats:italic>E</jats:italic> <jats:italic>+</jats:italic> <jats:italic>N</jats:italic>), where <jats:italic>s</jats:italic> and <jats:italic>N</jats:italic> are nucleophile‐specific parameters and <jats:italic>E</jats:italic> is an electrophile‐specific parameter, has recently been employed to characterize further classes of nucleophiles (phosphines, amines, isonitriles, trifluoromethanesulfonyl‐substituted carbanions) and electrophiles (2‐benzylideneindan‐1,3‐diones and benzylidenebarbituric acids). Practical applications of the reactivity parameters <jats:italic>E</jats:italic>, <jats:italic>N</jats:italic> and <jats:italic>s</jats:italic> for developing Friedel–Crafts alkylations in neutral alcoholic or aqueous solution and for characterizing nucleophilic organocatalysts will be discussed. Eventually, a new correlation equation will be presented, which includes Eqn (1), the Ritchie equation (nucleophilic additions to stabilized carbocations), and the Swain–Scott equation (nucleophilic substitutions of methyl halides) as special cases. Copyright © 2008 John Wiley &amp; Sons, Ltd.</jats:p>","is_dataset_classified":null,"base_score":5.823045895483019,"endowment":5.823045895483019,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"18998783","pmcid":null,"openalex_id":"https://openalex.org/W2033145782","authors":[],"funders":[{"funder_name":"Deutsche Forschungsgemeinschaft","grant_id":"Ma 673/21-2","title":null},{"funder_name":"Deutsche Forschungsgemeinschaft","grant_id":"SFB 749","title":null},{"funder_name":"Deutsche Forschungsgemeinschaft","grant_id":"unidentified","title":"unidentified"}],"total_grants":3,"fwci":13.7545,"citation_percentile":0.99393997,"influential_citations":0,"citation_trend":[{"year":2012,"count":29},{"year":2013,"count":20},{"year":2014,"count":23},{"year":2015,"count":18},{"year":2016,"count":16},{"year":2017,"count":19},{"year":2018,"count":14},{"year":2019,"count":13},{"year":2020,"count":16},{"year":2021,"count":16},{"year":2022,"count":23},{"year":2023,"count":15},{"year":2024,"count":16},{"year":2025,"count":15},{"year":2026,"count":8}],"oa_status":"closed","license":"Wiley Online Library User Agreement","oa_locations":[{"url":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fpoc.1325","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/poc.1325","host_type":"publisher"},{"url":"https://doi.org/10.1002/poc.1325","host_type":"journal"},{"url":"https://dx.doi.org/10.1002/poc.1325","host_type":""}],"fields_of_study":["Chemical Reaction Mechanisms","Synthesis of Indole Derivatives","Organic Chemistry Cycloaddition Reactions","01 natural sciences","0104 chemical sciences"],"mesh_terms":[],"keywords":["Nucleophile","Chemistry","Electrophile","Carbocation","Carbanion","Computational chemistry","Alkylation","Reactivity (psychology)","Aqueous solution","Medicinal chemistry","Halide","Organic chemistry","Catalysis"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Clean water and sanitation"}],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-07-19T02:00:50.119011Z","pmid":null,"pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}