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Supernucleophilic systems based on functionalized surfactants in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids. III. Reactivity of mixed micellar systems based on tetraalkylammonium and imidazolium surfactants

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Abstract

Reactivity of mixed micellar systems based on the functionalized imidazolium and tetraalkylammonium surfactanats in the reaction of cleavage of 4-nitrophenyl ethyl ethylphosphonate was studied. Replacing of an imidazolium fragment in the detergent structure with a tetraalkylammonium one reveals decreasing the substrate solubilization efficiency. In the case of dimeric surfactants, the nucleophilicity of the oximate fragment is considerably (ca. 2 times) decreased thus additionally decreasing the rate of cleavage of the organophosphorus substarte. Therefore the nature of the cationic center in the head group may affect the extent of the observed micellar effects of functionalized surfactants.

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Kharkov shosse 50, Kiev, 02160, Ukraine

    T. M. Prokop’eva, I. V. Kapitanov, I. A. Belousova, A. E. Shumeiko, M. L. Kostrikin, M. K. Turovskaya, N. G. Razumova & A. F. Popov

  2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine

    I. V. Kapitanov & A. E. Shumeiko

Authors
  1. T. M. Prokop’eva
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  2. I. V. Kapitanov
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  3. I. A. Belousova
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  4. A. E. Shumeiko
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  5. M. L. Kostrikin
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  6. M. K. Turovskaya
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  7. N. G. Razumova
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  8. A. F. Popov
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Correspondence to I. V. Kapitanov.

Additional information

Original Russian Text © T.M. Prokop’eva, I.V. Kapitanov, I.A. Belousova, A.E. Shumeiko, M.L. Kostrikin, M.K. Turovskaya, N.G. Razumova, A.F. Popov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 8, pp. 1105–1112.

For communication II, see [1].

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Prokop’eva, T.M., Kapitanov, I.V., Belousova, I.A. et al. Supernucleophilic systems based on functionalized surfactants in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids. III. Reactivity of mixed micellar systems based on tetraalkylammonium and imidazolium surfactants. Russ J Org Chem 51, 1083–1090 (2015). https://doi.org/10.1134/S1070428015080047

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  • DOI: https://doi.org/10.1134/S1070428015080047

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