Advertisement

Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Effect of sodium dodecyl sulfate on the reactivity of 2-dimethylaminomethylphenol with 4-nitrophenylbis(chloromethyl)phosphinate

  • 21 Accesses

  • 1 Citations

Abstract

The reactivity of 2-dimethylaminomethylphenol (1) toward 4-nitrophenylbis(chloromethyl)phosphinate (2) was studied in micellar solutions and in the lyotropic liquid-crystalline mesophase of the sodium dodecyl sulfate (SDS)-water system. The reaction between1 and2 is inhibited in the presence of SDS, which is explained by the shift of the acid-base equilibrium of1 toward the formation of a nonreactive protonated form.

This is a preview of subscription content, log in to check access.

References

  1. 1.

    C. A. Bunton and L. Robinson,J. Org. Chem., 1969,34, 773.

  2. 2.

    C. A. Bunton, M. M. Mhala, and J. R. Moffatt,J. Phys. Chem., 1989,93, 7851.

  3. 3.

    I. S. Ryzhkina, L. A. Kudryavtseva, V. E. Bel'skii, I. E. Ismaev, V. I. Morozov, A. V. Il'yasov, and B. E. Ivanov,Zh. Obshch. Khim., 1990,60, 820 [J. Gen. Chem. USSR, 1990,60 (Engl. Transl.)].

  4. 4.

    I. S. Ryzhkina, L. A. Kudryavtseva, V. E. Bel'skii, and B. E. Ivanov,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 555 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991,40, 478 (Engl. Transl.)].

  5. 5.

    S. B. Sawin, R. K. Chernova, and S. N. Shtykov,Poverkhnostno-aktivnye veshchestva [Surfactants], Nauka, Moscow, 1991, 29 p. (in Russian).

  6. 6.

    A. B. Teitel'baum, K. A. Derstuganova, N. A. Shishkina, L. A. Kudryavtseva, V. E. Bel'skii, and B. E. Ivanov,Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 803 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980,29, 538 (Engl. Transl.)].

  7. 7.

    V. E. Bel'skii, L. A. Kudryavtseva, O. M. Il'ina, and B. E. Ivanov,Zh. Obshch. Khim., 1979,49, 2470 [J. Gen. Chem. USSR, 1979,49 (Engl. Transl.)].

  8. 8.

    L. A. Val'kova and N. V. Usol'tseva,Kolloid. Zh., 1986,48, 339 [Colloid. J. USSR, 1986,48 (Engl. Transl.)].

  9. 9.

    Advances in Physical Organic Chemistry, Ed. V. Gold,8, Academic Press, London, New York, 1970.

  10. 10.

    I. S. Ryzhkina, R. A. Shagidullina, L. A. Kudryavtseva, I. E. Ismaev, and B. E. Ivanov,Izv. Akad. Nauk, Ser. Khim., 1994, 242 [Russ. Chem. Bull, 1994,43, 219 (Engl. Transl.)].

  11. 11.

    R. A. Shagidullina, I. S. Ryzhkina, A. B. Mirgorodskaya, L. A. Kudryavtseva, V. E. Bel'skii, and B. E. Ivanov,Izv. Akad. Nauk, Ser. Khim., 1994, 1215 [Russ. Chem. Bull., 1994,43, 1149 (Engl. Transl.)].

  12. 12.

    V. A. Savilova and N. M. Oleinik,Mekhanizmy deistviya organicheskikh katalizatorov. Bifunktsional'nyi i vnutri-molekulyarnyi kataliz [Mechanisms of Action of Organic Catalysts: Bifunctional and Intramolecular Catalysis], Naukova Dumka, Kiev, 1990, 153 p. (in Russian).

  13. 13.

    A. I. Rusanov,Mitselloobrazovanie v rastvorakh poverkhnost-noaktivnykh veshchestv [Micelle Formation in Surfactant Solutions], Khimiya, St. Petersburg, 1992, 280 p. (in Russian).

  14. 14.

    B. Lindman and H. Wennerstrom, inTopics in Current Chemistry,87, Springer, Berlin, 1980.

  15. 15.

    E. Tomplinson, S. S. Davis, and G. I. Mukhayer, inSurfactants in Solution, Ed K. L. Mittal,1, Plenum Press, New York, 1979.

Download references

Author information

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1959–1962, October, 1995.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Ryzhkina, I.S., Kudryavtseva, L.A. & Usol'tseva, N.V. Effect of sodium dodecyl sulfate on the reactivity of 2-dimethylaminomethylphenol with 4-nitrophenylbis(chloromethyl)phosphinate. Russ Chem Bull 44, 1879–1882 (1995). https://doi.org/10.1007/BF00707216

Download citation

Key words

  • micelles
  • liquid crystals
  • rate constant
  • sodium dodecyl sulfate
  • 2-dimethyl-aminomethylphenol
  • 4-nitrophenylbis(chloromethyl)phosphinate