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Supernucleophilic systems based on functionalized surfactants in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids: II. Influence of the length of hydrophobic alkyl substituents on micellar effects of functionalized monomeric and dimeric imidazolium surfactants

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Abstract

New dimeric functionalized surfactants, 3,3′-[2-(hydroxyimino)propan-1,3-diyl]bis(1-alkyl-1H-imidazol-3-ium) dichlorides (Alk = C12H25, C14H29, C16H33), underlie the supernucleophilic microorganized systems capable of abnormally fast cleavage of acyl-containing substrates. Micellar effects both of monomeric and dimeric imidazolium surfactants in the cleavage processes of 4-nitrophenyl esters of diethylphosphonic, diethylphosphoric, and 4-toluenesulfonic acids are governed mostly by the hydrophobicity of the reaction components (acceleration ∼102–103 times). The unquestionable advantage of dimeric surfactants is their especially low critical micelle concentrations (≤10−5 mol L−1), providing a possibility to attain the same micellar effects at the surfactant concentration lower by an order of magnitude (and yet even lower) than in the case of monomeric analogs.

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, ul. R. Luksemburg 70, Donetsk, 83114, Ukraine

    I. V. Kapitanov, I. A. Belousova, A. E. Shumeiko, M. L. Kostrikin, T. M. Prokop’eva & A. F. Popov

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  1. I. V. Kapitanov
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  2. I. A. Belousova
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  3. A. E. Shumeiko
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  4. M. L. Kostrikin
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  5. T. M. Prokop’eva
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  6. A. F. Popov
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Correspondence to I. V. Kapitanov.

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Original Russian Text © I.V. Kapitanov, I.A. Belousova, A.E. Shumeiko, M.L. Kostrikin, T.M. Prokop’eva, A.F. Popov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 5, pp. 706–715.

For communication I, see [1].

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Kapitanov, I.V., Belousova, I.A., Shumeiko, A.E. et al. Supernucleophilic systems based on functionalized surfactants in the decomposition of 4-nitrophenyl esters derived from phosphorus and sulfur acids: II. Influence of the length of hydrophobic alkyl substituents on micellar effects of functionalized monomeric and dimeric imidazolium surfactants. Russ J Org Chem 50, 694–704 (2014). https://doi.org/10.1134/S1070428014050133

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  • DOI: https://doi.org/10.1134/S1070428014050133

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