Nucleophilic ion pairs. 8. Facile nucleophilic cleavage of dinitrophenyl sulfate in the presence of micellar zwitterionic hydroxamates.
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概要
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The sulfate transfer reaction from dinitrophenyl sulfate to hydroxamate nucleophiles was studied in the presence of several types of aqueous micelles at 30 °C, pH 8–9. The zwitterionic hydroxamate was a nucleophile much better than the anionic hydroxamate in the CTAB micelle. The kinetic behavior of the zwitterionic hydroxamate nucleophile was not straightforward and the reactivity of the nucleophile increased with the increase in the relative concentration of the nucleophile and surfactant. These results in the CTAB micelle was analyzed in terms of the two phase model and the rate enhancement relative to the nonmicellar reaction was attributed to substrate binding in the micellar phase and the micellar activation of the hydroxamate nucleophile. The cleavage of dinitrophenyl sulfate by the micellar zwitterionic nucleophile was faster than that by the nonmicellar hydroxamate and the water cleavage by factors of <I>ca.</I> 10<SUP>4</SUP> and more than 10<SUP>7</SUP>, respectively: the fastest cleavage ever observed at the ambient condition.
- 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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Sakamoto Tetsuo
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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