{"doi":"10.1002/ejoc.200900299","title":"Synthesis and Characterization of Novel Quinone Methides: Reference Electrophiles for the Construction of Nucleophilicity Scales","abstract":"<jats:title>Abstract</jats:title><jats:p>Novel synthetic routes to the aryl‐substituted quinonemethides <jats:bold>3a</jats:bold>–<jats:bold>f</jats:bold> have been developed, and a previously reported Mannich approach has been used for the syntheses of the acceptor substituted quinone methides <jats:bold>2e</jats:bold>–<jats:bold>g</jats:bold>. The second‐order rate constants for the reactions of <jats:bold>3c</jats:bold>–<jats:bold>f</jats:bold> and <jats:bold>2e</jats:bold>–<jats:bold>g</jats:bold> with the carbanions <jats:bold>9a</jats:bold>–<jats:bold>h</jats:bold> were determined photometrically in DMSO. With Equation (1), log <jats:italic>k</jats:italic><jats:sub>2</jats:sub> = <jats:italic>s</jats:italic> (<jats:italic>N</jats:italic> + <jats:italic>E</jats:italic>), and the known nucleophilicity parameters <jats:italic>N</jats:italic> and <jats:italic>s</jats:italic> for the carbanions <jats:bold>9a</jats:bold>–<jats:bold>h</jats:bold>, it was possible to calculate the electrophilicity parameters <jats:italic>E</jats:italic> for these quinone methides. With <jats:italic>E</jats:italic> parameters between –12 and –17, these readily accessible quinone methides are recommended as reference electrophiles for the construction of nucleophilicity scales.(© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2009)</jats:p>","journal":"European Journal of Organic Chemistry","year":2009,"id":47157,"datarank":4.005050685420129,"base_score":4.795790545596741,"endowment":4.795790545596741,"self_citation_contribution":0.7193685818395114,"citation_network_contribution":3.2856821035806183,"self_endowment_contribution":0.7193685818395114,"citer_contribution":3.2856821035806183,"corpus_percentile":null,"corpus_rank":null,"citation_count":120,"citer_count":76,"citers_with_citation_signal":72,"citers_with_endowment":72,"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":217688,"name":"Nathalie Hampel","orcid":null,"position":1,"is_corresponding":false},{"id":217689,"name":"Thomas Singer","orcid":null,"position":2,"is_corresponding":false},{"id":203005,"name":"Armin R. 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The second‐order rate constants for the reactions of <jats:bold>3c</jats:bold>–<jats:bold>f</jats:bold> and <jats:bold>2e</jats:bold>–<jats:bold>g</jats:bold> with the carbanions <jats:bold>9a</jats:bold>–<jats:bold>h</jats:bold> were determined photometrically in DMSO. With Equation (1), log <jats:italic>k</jats:italic><jats:sub>2</jats:sub> = <jats:italic>s</jats:italic> (<jats:italic>N</jats:italic> + <jats:italic>E</jats:italic>), and the known nucleophilicity parameters <jats:italic>N</jats:italic> and <jats:italic>s</jats:italic> for the carbanions <jats:bold>9a</jats:bold>–<jats:bold>h</jats:bold>, it was possible to calculate the electrophilicity parameters <jats:italic>E</jats:italic> for these quinone methides. With <jats:italic>E</jats:italic> parameters between –12 and –17, these readily accessible quinone methides are recommended as reference electrophiles for the construction of nucleophilicity scales.(© Wiley‐VCH Verlag GmbH &amp; Co. 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