Advertisement

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

Relationship between the reactivity of aliphatic nitro-compounds in protolytic reactions and reactions op nucleophilic addition to the carbonyl group

Conclusions

  1. 1.

    The presence of a correlation between the basicity with respect to hydrogen of carbanions of nitrocompounds and their basicity with respect to carbon in the reaction series of acetaldehyde and formaldehyde was demonstrated.

  2. 2.

    The basicity of carbanions with respect to carbon in the series of acetaldehyde is two orders of magnitude less than the basicity of the same carbanions in the series of formaldehyde. This phenomenon was explained from the standpoint of differences in the steric stress in the molecules of the nitroalcohols formed by condensation of the nitro-compounds with acetaldehyde and formaldehyde.

  3. 3.

    The nucleophilicity of anions of nitro-compounds with respect to carbon varies correspondingly to the nucleophilicity of these anions with respect to hydrogen.

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

Literature cited

  1. 1.

    K. K. Ingold, Reaction Mechanism and the Structure of Organic Compounds [Russian translation], Chapter12, IL (1959), p. 542.

  2. 2.

    G. Becker, Introduction to the Electronic Theory of Organic Reactions [Russian translation], Mir (1965).

  3. 3.

    J. Hine and R. D. Weimar, Jr., J. Amer. Chem. Soc.,87, 3387 (1965).

  4. 4.

    R. G. Pearson and I. Songstad, J. Amer. Chem. Soc.,89, 1827 (1967).

  5. 5.

    T. N. Hall, Tetrahedron,19, 115 (1963).

  6. 6.

    T. N. Hall, J. Organ. Chem.,29, 3587 (1964).

  7. 7.

    T. N. Hall, J. Organ. Chem.,30, 3157 (1965).

  8. 8.

    Yu. N. Belokon' and V. M. Belikov, Izv. Akad. Nauk SSSR, Ser. Khim., 528 (1967).

  9. 9.

    V. M. Belikov, Yu. N. Belokon', N. G. Faleev, and Ts. B. Korchemnaya, Izv. Akad. Nauk SSSR, Ser. Khim., 1477 (1968).

  10. 10.

    V. M. Belikov, Yu. N. Belokon', N. S. Martinkova, and N. G. Faleev, Izv. Akad. Nauk SSSR, Ser. Khim., 2130 (1969).

  11. 11.

    D. Turnbull and S. H. Maron, J. Amer. Chem. Soc.,65, 212 (1943).

  12. 12.

    V. I. Slovetskin, S. A. Shevelev, A. A. Fainzil'berg, and S. S. Novikov, Zh. Vses. Khim. Ob-va im. Mendeleeva,6, 707 (1961).

  13. 13.

    V. M. Belikov, Yu. N. Belokon', Ts. B. Korchemnaya, and N. G. Faleev, Izv. Akad. Nauk SSSR, Ser. Khim., 327 (1968).

  14. 14.

    L. C. Gruen and P. T. Mc Tigue, J. Chem. Soc., 5217 (1963).

  15. 15.

    E. A. Moelwyn-Hughes and D. N. Glew, Proc. Roy. Soc. (A),212, 210 (1952).

Download references

Author information

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2136–2141, October, 1969.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Belikov, V.M., Belokon', Y.N., Martinkova, N.S. et al. Relationship between the reactivity of aliphatic nitro-compounds in protolytic reactions and reactions op nucleophilic addition to the carbonyl group. Russ Chem Bull 18, 1992–1996 (1969). https://doi.org/10.1007/BF00906608

Download citation

Keywords

  • Hydrogen
  • Acetaldehyde
  • Formaldehyde
  • Carbonyl
  • Carbonyl Group