Reactivity of Inorganic α-Nucleophiles in Acyl Transfer in Aqueous and Micellar Media: IV. Peroxyhydrolysis of Acyl Derivatives in Organized Microheterogeneous Systems1

IF 0.8 4区化学 Q4 CHEMISTRY, ORGANIC

Russian Journal of Organic Chemistry Pub Date : 2024-04-29 DOI:10.1134/s1070428024020106

M. K. Turovskaya, I. A. Belousova, N. G. Razumova, T. S. Gaidash, T. M. Prokop’eva, A. A. Kotenko, V. A. Mikhailov

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Abstract

The micellar effects in the perhydrolysis and base-catalyzed hydrolysis of 4-nitrophenyl esters of phosphoric, phosphonic, and toluenesulfonic acids in organized microheterogeneous systems based on dicationic [Gemini surfactant AlkIm⁺–(CH₂)₃–Im⁺Alk∙2Br^–, where Alk = C₁₂H₂₅ or C₁₄H₂₉ (GS)] and monocationic (AlkIm⁺CH₃∙Br^–, where Alk=C₁₂H₂₅ or C₁₄H₂₉) surfactants have been analyzed. The reagent concentrations have been found to be the main factor responsible for micellar catalysis. The hydroperoxide α-effect defined as the ratio of the second-order rate constants of perhydrolysis and base-catalyzed hydrolysis is preserved and, depending on the nature of the surfactant and the substrate, may reach ~ 100.

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无机 α 亲核物在水介质和微胶囊介质中酰基转移中的反应性：IV.有组织微异质体系中酰基衍生物的过氧化水解1

摘要在基于双阳离子[双子表面活性剂 AlkIm+-(CH2)3-Im+Alk∙2Br-, 其中 Alk = C12H25 或 C14H29 (GS)] 和单阳离子[AlkIm+CH3∙Br-, 其中 Alk = C12H25 或 C14H29 (GS)] 的有组织微异构体系中，磷酸、膦酸和甲苯磺酸的 4-硝基苯基酯的过水解和碱催化水解的胶束效应、其中 Alk=C12H25 或 C14H29 (GS)] 和单配位（AlkIm+CH3∙Br-，其中 Alk=C12H25 或 C14H29）表面活性剂的有组织微均质系统进行了分析。结果发现，试剂浓度是导致胶束催化作用的主要因素。过氧化氢 α 效应（定义为过水解和碱催化水解的二阶速率常数之比）得以保留，并且根据表面活性剂和底物的性质，可达到约 100。

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来源期刊

Russian Journal of Organic Chemistry 化学-有机化学

CiteScore

1.40

自引率

25.00%

发文量

139

审稿时长

3-6 weeks

期刊介绍： Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.

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