Skip to main content
Log in

Structure-reactivity cross correlations in nucleophilic substitution: Isoparametricity and transition-state structure

  • Published:
Theoretical and Experimental Chemistry Aims and scope

Abstract

Data are surveyed on cross correlations for nucleophilic substitution at benzoyl, benzyl, and benzhydryl carbon atoms. The cross correlation coefficients and isoparametric points are used to interpret the reaction mechanisms.

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. Yu. N. Molin and I. V. Melikhov,Zh. Vsesoyus. Khim. Obshch. im. D. I. Mendeleeva,35, No. 2, 223–228 (1990).

    Google Scholar 

  2. V. A. Legasov and A. L. Buchachenko,Usp. Khim.,55, No. 12, 1949–1978 (1986).

    CAS  Google Scholar 

  3. A. I. Lesnikovich and S. V. Levchik,Correlations in Modern Chemistry [in Russian], Universitetskoe, Minsk (1989).

    Google Scholar 

  4. V. A. Pal'm,Principles of Quantitative Organic Reaction Theory [in Russian], Khimiya, Leningrad (1967).

    Google Scholar 

  5. V. A. Pal'm,Principles of Quantitative Organic Reaction Theory [in Russian], Khimiya, Leningrad (1977).

    Google Scholar 

  6. Yu. A. Zhdanov and V. I. Minkin,Correlation Analysis in Organic Chemistry [in Russian], Izd. Rostov Univ., Rostov-on-Don (1966).

    Google Scholar 

  7. J. E. Leffler and E. Grunwald,Rates and Equilibria of Organic Reactions, Wiley, New York and London (1963).

    Google Scholar 

  8. C. Hansch, A. Leo, and R. W. Taft,Chem. Rev.,91, No. 2, 165–195 (1991).

    Article  CAS  Google Scholar 

  9. I. V. Trushkov, N. D. Chuvylkin, A. S. Koz'min, and N. S. Zefirov,Izv. Akad. Nauk, Ser. Khim., No. 5, 804–826 (1995).

    Google Scholar 

  10. J.-E. Dubois, M.-F. Ruasse, and A. Argile,J. Am. Chem. Soc.,106, No. 17, 4840–4845 (1984).

    Article  CAS  Google Scholar 

  11. W. P. Jencks,Chem. Rev.,85, No. 6, 511–527 (1985).

    Article  CAS  Google Scholar 

  12. I. Lee,Chem. Soc. Rev.,19, 317–333 (1990).

    Article  CAS  Google Scholar 

  13. I. Lee,Adv. Phys. Org. Chem.,27, 57–117 (1992).

    CAS  Google Scholar 

  14. I. V. Shpan'ko,Mendeleev Commun., 119–120 (1991).

  15. Ya. Kh. Riikoya, Kh. R. Timotkheus, and V. A. Pal'm,Reakts. Sposobnost' Org. Soedin.,14, No. 4, 522–540 (1977).

    Google Scholar 

  16. V. Palm, V. Timotheus, H. Pooga, et al.,Org. React.,30, No. 1, 69–72 (1996).

    CAS  Google Scholar 

  17. V. Palm and S. Kaasik,Org. React.,30, No. 1, 73–83 (1996).

    CAS  Google Scholar 

  18. B. V. Gidaspov, P. A. Ivanov, S. A. Pivovarov, and V. F. Selivanov,Reakts. Sposobnost' Org. Soedin.,8, No. 1, 49–61 (1971).

    CAS  Google Scholar 

  19. S. A. Pivovarov, V. F. Selivanov, and B. V. Gidaspov,Reakts. Sposobnost' Org. Soedin.,12, No. 2, 307–328 (1975).

    Google Scholar 

  20. S. A. Pivovarov, V. F. Selivanov, B. I. Istomin, and B. V. Gidaspov,Reakts. Sposobnost' Org. Soedin.,12, No. 2, 367–382 (1975).

    Google Scholar 

  21. V. A. Pal'm and B. I. Istomin,Reakts. Sposobnost' Org. Soedin.,6, No. 2, 427–437 (1969).

    Google Scholar 

  22. I. V. Shpanko, S. I. Kim, H. J. Koh, and I. Lee,Bull. Korean Chem. Soc.,16, No. 6, 533–538 (1995).

    CAS  Google Scholar 

  23. B. I. Istomin, S. A. Pivovarov, V. F. Selivanov, et al.,Reakts. Sposobnost' Org. Soedin.,12, No. 2, 289–300 (1975).

    Google Scholar 

  24. C. Johnson,Hammet's Equation [Russian translation], Mir, Moscow (1977).

    Google Scholar 

  25. D. J. McLennan,Tetrahedron,34, No. 15, 2331–2341 (1978).

    Article  CAS  Google Scholar 

  26. I. V. Shpan'ko, G. D. Titskii, L. M. Litvinenko, and M. A. Eremeev,Reakts. Sposobnost' Org. Soedin.,10, No. 1, 187–202 (1973).

    Google Scholar 

  27. I. V. Shpan'ko, A. N. Goncharov, E. V. Chetverova, and E. E. Likhomanenko,Zh. Org. Khim.,22, No. 7, 1432–1438 (1986).

    Google Scholar 

  28. I. V. Shpan'ko, A. N. Goncharov, and L. M. Litvinenko,Zh. Org. Khim.,13, No. 4, 761–766 (1977).

    Google Scholar 

  29. G. D. Titskii, I. V. Shpan'ko, L. M. Litvinenko, and V. M. Shuliko,Reakts. Sposobnost' Org. Soedin.,8, No. 1, 39–47 (1971).

    CAS  Google Scholar 

  30. A. N. Goncharov, I. V. Shpan'ko, E. V. Chetverova, and E. E. Likhomanenko,Ukr. Khim. Zh.,52, No. 10, 1077–1082 (1986).

    CAS  Google Scholar 

  31. A. N. Goncharov, I. V. Shpan'ko, and A. P. Korostylev,Zh. Org. Khim.,17, No. 5, 972–978 (1981).

    Google Scholar 

  32. I. V. Shpanko,Org. React.,31, No. 1, 177–180 (1997).

    CAS  Google Scholar 

  33. I. V. Shpan'ko, L. M. Litvinenko, A. P. Korostylev, et al.,Dokl. Akad. Nauk SSSR,234, No. 6, 1358–1361 (1977).

    Google Scholar 

  34. I. M. Serebryakov, I. V. Shpanko, and N. M. Oleinik,Org. React.,28, No. 1, 6–11 (1993).

    CAS  Google Scholar 

  35. A. Pross,Adv. Phys. Org. Chem.,14, 69–132 (1977).

    Article  CAS  Google Scholar 

  36. C. D. Johnson,Chem. Rev.,75, No. 6, 755–765 (1975).

    Article  CAS  Google Scholar 

  37. M. Štrasak,Chem. Listy,76, No. 9, 911–943 (1982).

    Google Scholar 

  38. I. V. Shpan'ko and I. M. Serebryakov,Ukr. Khim. Zh.,60, No. 11, 793–796 (1994).

    Google Scholar 

  39. I. M. Serebryakov, N. M. Oleinik, and I. V. Shpanko,Org. React.,28, No. 1, 12–17 (1993).

    CAS  Google Scholar 

  40. I. V. Shpanko, I. M. Serebryakov, N. M. Oleinik, and B. V. Panchenko,Org. React.,30, No. 1, 3–6 (1996).

    CAS  Google Scholar 

  41. I. V. Shpanko and I. M. Serebryakov,Org. React.,30, No. 1, 7–11 (1996).

    CAS  Google Scholar 

  42. R. Schmid and V. N. Sapunov,Informal Kinetics [Russian translation], Mir, Moscow (1985).

    Google Scholar 

Download references

Authors

Additional information

Donetsk State University, 24 Universitetskaya ul., Donetsk 340055, Ukraine. Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 35, No. 2, pp. 67–78, March–April, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shpan'ko, I.V. Structure-reactivity cross correlations in nucleophilic substitution: Isoparametricity and transition-state structure. Theor Exp Chem 35, 63–74 (1999). https://doi.org/10.1007/BF02511491

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02511491

Keywords

Navigation