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Kinetics of alkaline hydrolysis of phenyl dimethylphosphinothionates in water-dioxane mixtures

  • Physical Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The kinetics of the alkaline hydrolysis of a series of esters Me2P(S)OC6H4X-p at 25°C in water-dioxane mixtures of various compositions was studied spectrophotometrically.

  2. 2.

    It was shown that the principle of linearity of the free-energy change is applicable to the effects of the structure of the aryloxy leaving group and the composition of the medium on the rate constant of hydrolysis and that the effect of these factors in the given reaction series is essentially nonadditive.

  3. 3.

    The monotypic effect of the structure of the leaving group and the composition of the aqueous-organic binary solvent on the alkaline hydrolysis reactions of the studied phosphinothionates and phenyl acetates suggests that alkaline hydrolysis of organophosphorus esters occurs according to an addition-abstraction mechanism with attack of the ester molecule by the HO− anion in the limiting step.

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Literature cited

  1. P. Haake, D. R. McCoy, W. Okamura, S. R. Alpha, Shi Yin Yong, D. A. Tyssee, J. P. McNeal, and R. D. Cook, Tetrahedron Lett., 5243 (1968).

  2. R. D. Cook, C. E. Diebert, W. Schwarz, P. C. Turley, and P. Haake, J. Am. Chem. Soc.,95, 8088 (1973).

    Google Scholar 

  3. B. L. Finkel'shtein, Yu. I. Sukhorukov, and B. I. Istomin, Reactivity of Organic Compounds [in Russian], Vol. 14 (1977), p. 187.

    Google Scholar 

  4. V. E. Bel'skii, L. A. Kudryavtsev, O. M. Il'ina, and B. E. Ivanov, Zh. Obshch. Khim.,49, 2470 (1979).

    Google Scholar 

  5. G. D. Eliseeva, B. I. Istomin, and A. V. Kalabina, Zh. Obshch. Khim.,48, 1901 (1978);50, 1901 (1980).

    Google Scholar 

  6. G. D. Eliseeva, B. I. Istomin, and A. V. Kalabina, Zh. Obshch. Khim.,49, 1906 (1979).

    Google Scholar 

  7. B. I. Istomin, G. D. Eliseeva, and A. V. Kalabina, Zh. Obshch. Khim.,50, 1186 (1980).

    Google Scholar 

  8. B. I. Istomin, B. N. Bazhenov, G. D. Eliseeva, and B. L. Finkel'shtein, Reactivity of Organic Compounds [in Russian], Vol. 16 (1979), p. 197.

    Google Scholar 

  9. B. I. Istomin, B. N. Bazhenov, G. D. Eliseeva, and B. L. Finkel'shtein, Reactivity of Organic Compounds [in Russian], Vol. 16 (1979), p. 187.

    Google Scholar 

  10. V. A. Pal'm and B. I. Istomin, Reactivity of Organic Compounds [in Russian], Vol. 6 (1969), p. 427.

    Google Scholar 

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Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR, USSR

    E. L. Zhdankovich, B. I. Istomin & M. G. Voronkov

Authors
  1. E. L. Zhdankovich
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  2. B. I. Istomin
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  3. M. G. Voronkov
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1264–1267, June, 1981.

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Zhdankovich, E.L., Istomin, B.I. & Voronkov, M.G. Kinetics of alkaline hydrolysis of phenyl dimethylphosphinothionates in water-dioxane mixtures. Russ Chem Bull 30, 998–1001 (1981). https://doi.org/10.1007/BF00950280

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  • DOI: https://doi.org/10.1007/BF00950280

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