Solvent polarity and organic reactivity in mixed solvents: Evidence using a reactive molecular probe to assess the role of preferential solvation in aqueous alcohols

TW Bentley, DN Ebdon, EJ Kim…

文献索引：Bentley, T. William; Ebdon, David N.; Kim, Eun-Ju; In, Sun Koo Journal of Organic Chemistry, 2005 , vol. 70, # 5 p. 1647 - 1653

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被引用次数: 26

摘要

Product selectivities [S=([ester product]/[acid product])×([water]/[alcohol solvent])] are reported for solvolyses of p-methoxybenzoyl chloride (2) in aqueous methanol, ethanol, 2, 2, 2-trifluoroethanol, n-propyl alcohol, isopropyl alcohol, and tert-butyl alcohol at 25, 35, and 45° C. S values are small and depend significantly on the alcohol cosolvent, varying from 1.3 in methanol to 0.1 in tert-butyl alcohol, but S depends only slightly on the solvent ...