Nucleophilic ion pairs. 6. Catalytic hydrolysis of p-nitrophenyl acetate by zwitterionic hydroxamate nucleophiles in representative micellar systems.
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概要
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Several surfactant-like zwitterionic hydroxamates were synthesized and their reactions with <I>p</I>-nitrophenyl acetate were studied in water in comparison with those of simple, anionic hydroxamates. The zwitterionic hydroxamates showed enhanced reactivities in cationic, zwitterionic and nonionic micelles: 20–100 times relative to the nomicellar rate at pH 8.9, 30 °C. The rate enhancement was attributed to lowered p<I>K</I><SUB>a</SUB> values and to activation of the hydroxamate anion in the hydrophobic domain. The rate was suppressed in an anionic micelle because of the enhanced p<I>K</I><SUB>a</SUB> value. Deacylation of the acetyl hydroxamate intermediate was hydroxide-catalyzed. The enhanced reactivity of the zwitterionic hydroxamate in organic media was less sensitive to the water concentration than that of the hydroxamate ion pair. These results can be explained in terms of "<I>hydrophobic ion pair.</I>"
- 公益社団法人 日本化学会の論文
著者
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Kunitake Toyoki
Department Of Chemical Engineering & Technology Faculty Of Engineering Kyushu University
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Ando Reiko
Department of Organic Syntheis, Faculty of Engineering, Kyushu University
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Okahata Yoshio
Department of Applied Chemistry, Kyushu University 36
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Tanamachi Shoichi
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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