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Catalytic properties of polymer-colloid complexes based on polyethyleneimines and mono- and diquaternized 1,4-diazabicyclo[2.2.2]octane derivatives in the hydrolysis of phosphorus acids esters

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Abstract

It is established by spectrophotometry that polyethyleneimines, mono- (MQD) and diquaternized (DQD) hexadecyl derivatives of 1,4-diazabicyclo[2.2.2]octane, and mixed polymercolloid systems based thereon catalyze the hydrolysis of p-nitrophenyl alkyl chloromethylphosphonates. The catalysis efficiency depends on the structures of substrate, 1,4-diazabicyclo-[2.2.2]octane derivatives, and polyethyleneimine, pH of the medium, and the temperature. In the case of MQD, the catalytic effect changes from 20 to 80-fold with an increase in the length of phosphonate alkyl radical from R = OEt to R = OC6H13; the DQDs exhibit lower catalytic activity compared to the MQD. The most efficient catalysis (up to 90-fold acceleration) is observed for a mixed polyethylene—dicationic surfactant system where the surfactant contains the hydroxyethyl fragment in the head group, which is due to a favorable effect of the micellar microenvironment of reagents.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    T. N. Pashirova, E. P. Zhil´tsova, S. S. Lukashenko, L. Ya. Zakharova & A. I. Konovalov

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  1. T. N. Pashirova
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  2. E. P. Zhil´tsova
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  3. S. S. Lukashenko
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Correspondence to T. N. Pashirova.

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Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2879—2884, December, 2015.

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Pashirova, T.N., Zhil´tsova, E.P., Lukashenko, S.S. et al. Catalytic properties of polymer-colloid complexes based on polyethyleneimines and mono- and diquaternized 1,4-diazabicyclo[2.2.2]octane derivatives in the hydrolysis of phosphorus acids esters. Russ Chem Bull 64, 2879–2884 (2015). https://doi.org/10.1007/s11172-015-1242-6

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