Skip to main content
Log in

Influence of the structure of monoalkyl substituted ketenes upon the rate of their spontaneous hydrolysis in water

  • Published:
Reaction Kinetics and Catalysis Letters Aims and scope Submit manuscript

Abstract

The kinetics of spontaneous hydrolysis of monoalkylsubstituted ketenes has been studied. The influence of inductive and steric effects of substituents upon the rate has been quantitatively estimated in terms of ρσ-analysis. Increasing length and branching of alkyl substiuents decrease the rate of ketene hydrolysis.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. H.R. Seikaly, T.T. Tidwell: Tetrahedron,42, 2587 (1986).

    Google Scholar 

  2. T.T. Tidwell: Acc. Chem. Res.,23, 273 (1990).

    Google Scholar 

  3. N.L. Poon, D.P.N. Satchell: J. Chem. Soc. Perkin Trans. 2, 1485 (1986).

    Google Scholar 

  4. M.T. Nguyen, A.F. Hegarty: J. Am. Chem. Soc.,106, 1552 (1984).

    Google Scholar 

  5. Yu.G. Skrypnik, S.N. Lyashchuk: React. Kinet. Catal. Lett.,43, 283 (1991).

    Google Scholar 

  6. Yu.G. Skrypnik, V.P. Besrodnyi, S.N. Lyashchuk: Dokl. Akad. Nauk SSSR,321, 1028 (1991).

    Google Scholar 

  7. S.N. Lyashchuk, Yu.G. Skrypnik, V.P. Besrodnyi: React. Kinet. Catal. Lett.,46, 319 (1992).

    Google Scholar 

  8. L. Horner, E. Spietschka: Ann.,573, 17 (1951).

    Google Scholar 

  9. M.A. West: Techniques of Chemistry, Vol. 6, Pt. 2, Chap. 8, Wiley-Interscience, New York, 1986.

    Google Scholar 

  10. Tables of rates and equilibrium constants of heterolytic organic reactions. Ed. by V.A. Palm, VINITI, Moscow, Vol. 5, Pt. 2, p. 283, 1979 (in Russian).

    Google Scholar 

  11. M. Charton: J. Am. Chem. Soc.,97, 1552 (1975).

    Google Scholar 

  12. R.W. Taft: J. Am. Chem. Soc.,74, 3120 (1952).

    Google Scholar 

  13. E. Bothe, A.M. Dessouki, D. Schulte-Frohlinde: J. Phys. Chem.,84, 3270 (1980).

    Google Scholar 

  14. A.D. Allen, A.J. Kresge, N.P. Schepp, T.T. Tidwell: Canad. J. Chem.,65, 1719 (1987).

    Google Scholar 

  15. A.D. Allen, T.T. Tidwell: J. Am. Chem. Soc.,192, 2774 (1987).

    Google Scholar 

  16. E. Bothe, H. Meier, D. Schulte-Frohlinde, C. von Sonntag: Angew. Chem. Int. Ed. Engl.,15, 380 (1976).

    Google Scholar 

  17. B.M. Allen, A.F. Hegarty, P.O. Neill, M.T. Nguyen: J. Chem. Soc. Perkin Trans. 2, 927 (1992).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lyashchuk, S.N., Skrypnik, Y.G. Influence of the structure of monoalkyl substituted ketenes upon the rate of their spontaneous hydrolysis in water. React Kinet Catal Lett 52, 399–404 (1994). https://doi.org/10.1007/BF02067814

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02067814

Keywords

Navigation