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Reactivity of Inorganic α-Nucleophiles in Acyl Group Transfer Processes in Water and Surfactant Micelles: II.1 Alkaline Hydrolysis of Ethyl 4-Nitrophenyl Ethylphosphonate in Systems Based on Dimeric Cationic Surfactants

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Abstract

Alkaline hydrolysis of ethyl 4-nitrophenyl ethylphosphonate in organized nanosized systems based on dimeric surfactants and co-micelles [with cetyl(trimethyl)ammonium bromide as co-surfactant]. Transfer of the reaction from water to the micellar pseudophase accelerates the alkaline hydrolysis by a factor of 10 to 170. The maximum acceleration has been observed for tetraalkylammonium surfactant 16–3–16. The main factors responsible for micellar effects of surfactants are both substrate concentration and change of the reactivity of hydroxide ion in going from bulk water to surfactant micelles.

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, Donetsk, 83114, Ukraine

    T. M. Zubareva, I. A. Belousova, T. M. Prokop’eva, T. S. Gaidash, N. G. Razumova, B. V. Panchenko & V. A. Mikhailov

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  1. T. M. Zubareva
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  2. I. A. Belousova
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  3. T. M. Prokop’eva
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Correspondence to N. G. Razumova.

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Russian Text © The Author(s), 2020, published in Zhurnal Organicheskoi Khimii, 2020, Vol. 56, No. 1, pp. 70–77.

For communication I, see [1].

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Zubareva, T.M., Belousova, I.A., Prokop’eva, T.M. et al. Reactivity of Inorganic α-Nucleophiles in Acyl Group Transfer Processes in Water and Surfactant Micelles: II.1 Alkaline Hydrolysis of Ethyl 4-Nitrophenyl Ethylphosphonate in Systems Based on Dimeric Cationic Surfactants. Russ J Org Chem 56, 53–58 (2020). https://doi.org/10.1134/S1070428020010091

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