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

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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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Funding

This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, 283048, Donetsk, Russia

    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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  1. M. K. Turovskaya
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  2. I. A. Belousova
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  3. N. G. Razumova
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  4. T. S. Gaidash
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  5. T. M. Prokop’eva
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  7. V. A. Mikhailov
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Correspondence to A. A. Kotenko.

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Turovskaya, M.K., Belousova, I.A., Razumova, N.G. et al. Reactivity of Inorganic α-Nucleophiles in Acyl Transfer in Aqueous and Micellar Media: IV. Peroxyhydrolysis of Acyl Derivatives in Organized Microheterogeneous Systems1. Russ J Org Chem 60, 252–258 (2024). https://doi.org/10.1134/S1070428024020106

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