Skip to main content
Log in

Interaction of nicotine with π and σ electron acceptors

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

Interaction of nicotine with tetracyanoethylene and iodine was investigated spectrophotometrically and found to form strong CT complexes (n−π and n-σ*, respectively). The donor site involved in CT interaction is the pyrrolidine nitrogen. The nicotine-I2 complex exists as the ionic structure (nicotine) I+-I 3 . Formation constants of the CT complexes in various solvents were determined from 10 to 25°C and are discussed in terms of the nature of the electron acceptor and solvent polarity. Solid CT complexes were synthesized and were characterized by microchemical analysis and infrared spectra techniques.

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. A. M. Taha, A. K. S. Ahmad, C. S. Gomaa, and H. El-Fatatry,J. Pharm. Sci. 63, 1853 (1974).

    CAS  Google Scholar 

  2. C. Gomaa and A. Taha,J. Pharm. Sci. 64, 1398 (1975).

    CAS  Google Scholar 

  3. A. M. Taha and C. S. Gomaa,J. Pharm. Sci. 65, 986 (1976).

    CAS  Google Scholar 

  4. M. A. Elsayed, M. A. Abdel-Salam, N. A. Abdel-Salam, and Y. A. Mohamed,Planta Medica 34, 430 (1978).

    Article  CAS  Google Scholar 

  5. H. Abdine, M. A. Elsayed and Y. M. Elsayed,Analyst 103, 354 (1978).

    Article  CAS  Google Scholar 

  6. M. A. Elsayed,Pharmazie 34, 115 (1979).

    CAS  Google Scholar 

  7. A. Taha and G. Rücker,Arch. Pharm. (Weinheim) 310, 485 (1977).

    CAS  Google Scholar 

  8. M. A. Elsayed and S. P. Agarwal,Talanta 29, 535 (1982).

    Article  CAS  Google Scholar 

  9. R. H. Abu-Eithah, Z. E. Mobarak, and M. M. Abdou,Gazz. Chim. Ital. 118, 275 (1988).

    Google Scholar 

  10. W. J. Middleton, E. L. Little, D. D. Coffman, and V. A. Engelhardt,J. Am. Chem. Soc. 80, 2795 (1958).

    Article  CAS  Google Scholar 

  11. H. J. Shine and R. D. Goodin,J. Org. Chem. 35, 949 (1970).

    Article  CAS  Google Scholar 

  12. P. Bruni, G. Tasi, L. Gardellini, E. Giorgini, and P. Stipa,Spectrochim. Acta 45A, 519 (1989).

    CAS  Google Scholar 

  13. J. Bolard,J. Chim. Phys. 66, 221 (1969).

    CAS  Google Scholar 

  14. K. Wallenfels,Angew. Chem. 76, 326 (1964).

    Google Scholar 

  15. P. G. Farrell and R. K. Wojtowski,J. Chem. Soc. C, 1394 (1970).

    Google Scholar 

  16. W. Kiefer and H. J. Bernstein,Chem. Phys. Lett. 16, 5 (1972).

    Article  CAS  Google Scholar 

  17. L. Andrews, E. S. Prochaska, and A. Loewenschuss,Inorg. Chem. 19, 463 (1980).

    Article  CAS  Google Scholar 

  18. K. Kaya, N. Mikami, Y. Udagawa, and M. Ito,Chem. Phys. Lett. 16, 151 (1972).

    Article  CAS  Google Scholar 

  19. E. M. Nour, L. H. Chen, and J. Laane,J. Raman Spectrosc. 17, 467 (1986).

    Article  CAS  Google Scholar 

  20. M. Mizuno, J. Tanaka, and I. Harada,J. Phys. Chem. 85, 1789 (1981).

    Article  CAS  Google Scholar 

  21. M. A. Sliffkin,Spectrochim. Acta 20, 1543 (1964);21, 1391 (1965).

    Article  Google Scholar 

  22. H. A. Benesi and J. H. Hildebrand,J. Am. Chem. Soc. 71, 2703 (1949).

    Article  CAS  Google Scholar 

  23. R. L. Scott,Recl. Trav. Chim. Pays-Bas 75, 787 (1956).

    CAS  Google Scholar 

  24. E. G. C. Clark,Isolation and Identification of Drugs (Pharmaceutical Press, London I, 1978) p. 807.

    Google Scholar 

  25. R. S. Mulliken,J. Phys. Chem. 56, 801 (1952);Recl. Trav. Chim. Pays-Bas,75, 845 (1956);J. Chem. Phys. 61, 20 (1964).

    Article  CAS  Google Scholar 

  26. R. S. Mulliken and W. P. Person,Ann. Rev. Phys. Chem. 13, 107 (1962);J. Am. Chem. Soc. 91, 3409 (1969).

    Article  CAS  Google Scholar 

  27. R. Abu-Eittah and M. M. Hamed,Can. J. Chem. 57, 2337 (1979).

    Article  CAS  Google Scholar 

  28. G. G. Aloisi and S. Pignataro,J. Chem. Soc. Faraday Trans. 69, 534 (1973).

    Article  CAS  Google Scholar 

  29. R. M. Silverstein, C. C. Bassler, and T. C. Morrill,Spectrometric Idenfitication of Organic Compounds, 4th edn. (Wiley, New York, 1981) p. 135.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hamed, M.M.A. Interaction of nicotine with π and σ electron acceptors. J Solution Chem 22, 1151–1158 (1993). https://doi.org/10.1007/BF00651696

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00651696

Key words

Navigation