Skip to main content
SpringerLink
Log in

Comparative Study of the Structure of Rhodanine, Isorhodanine, Thiazolidine-2,4-dione, and Thiorhodanine

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Ab initio (HF and MP2 level) and semiempirical (AM1, PM3, MNDO) calculations on the relative stabilities and structures of the potential tautomeric forms of rhodanine, isorhodanine, thiazolidine-2,4-dione, and thiorhodanine are reported. Ab initio calculations predict that the thiooxo, oxothio, dioxo, and dithio tautomers are the most stable. These results correspond to the known experimental data. Infrared spectra of the investigated compounds were recorded for the region 4000-150 cm-1, and the characteristic bands were compared with ab initio calculated frequencies at the HF/3-21G(*)* level.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. G. A. Blokh, Ch. L. Melamed, A. I. Grichshuk, and L. P. Jaroshenko, Izv. Vysshikh Uchebn. Zavedenii. Tekhnol. Legkoi Prom., 4, 68 (1966); Chem. Abstr., 66, 11598 (1967).

    Google Scholar 

  2. S. Hirabayashi and Y. Nagaoka, Jpn. Kokai Tokkyo Koho JP 03 144 634; Chem. Abstr., 117, 160723 (1992).

    Google Scholar 

  3. H. Mifune and T. Tani, Jpn. Kokai Tokkyo Koho JP 04 195 036; Chem. Abstr., 118, 29894 (1993).

    Google Scholar 

  4. N. Khang, L. V. Minh, N. N. Vinh, T. M. Binh, P. G. Kohi, B. N. Dong, N. K. Lien, and B. K. Lien, Rev. Pharm., 110 (1986); Chem. Abstr., 109, 73374 (1988).

    Google Scholar 

  5. D. A. Clark, S. W. Goldstein, and B. Hulin, US Pat. 5 036 079; Chem. Abstr., 116, 83663 (1992).

    Google Scholar 

  6. W. A. Cetenko, D. T. Connor, J. Ch. Sirkar, R. J. Sorenson, and P. Ch. Unangst, Eur. Pat. Appl. EP 449 216; Chem. Abstr., 116, 128921 (1992).

    Google Scholar 

  7. R. M. Hindley, D. Haigh, and G. P. Cottam, PCT Int. Appl. WO 92 07 839; Chem. Abstr., 117, 212490 (1992).

    Google Scholar 

  8. R. F. Kletzien, S. D. Clarke, and R. G. Ulrich, Mol. Pharmacol., 41, 393 (1992); Chem. Abstr., 118, 610 (1993).

    Google Scholar 

  9. E. S. Raper, Coord. Chem. Rev., 61, 115 (1985).

    Google Scholar 

  10. P. Karagiannidis, S. K. Hadjikakou, P. Aslanidis, and A. Hountas, Inorg. Chim. Acta, 178, 27 (1990).

    Google Scholar 

  11. R. F. Guryeva and S. B. Savvin, Zhurn. Anal. Khim., 47, 1157 (1992).

    Google Scholar 

  12. J. Elguero, C. Marzin, A. R. Katritzky, and P. Linda, in The Tautomerism of Heterocycles, Acad. Press, New York, 1976, 453, 457, 462.

    Google Scholar 

  13. D. van der Helm, A. E. Lessor, and L. L. Merritt, Acta Crystallogr., 15, 1227 (1962).

    Google Scholar 

  14. G. R. Form, E. S. Raper, and T. C. Downie, Acta Crystallogr., B 31, 2181 (1975).

    Google Scholar 

  15. R. Hilal, H. Ead, and A. Osman, Appl. Spectrosc., 32, 557 (1978).

    Google Scholar 

  16. M. V. Andreocci, C. Cauletti, and L. Sestili, Spectrochim. Acta, A 40, 1087 (1984).

    Google Scholar 

  17. N. Valls, V. M. Segarra, E. Alcalde, A. Marin, and J. Elguero, J. Prakt. Chem., 327, 251 (1985).

    Google Scholar 

  18. V. Enchev, I. Petkov, and S. Chorbadjiev, Struct. Chem., 5, 225 (1994).

    Google Scholar 

  19. A. P. Grishchuk, Khim. Geterotsikl. Soedin., 372 (1966).

  20. R. S. Lebedev and I. V. Yakimenko, Izv. Vysshikh Uchebn. Zavedenii. Fizika, 15, 109 (1972).

    Google Scholar 

  21. M. Nencki, J. Prakt. Chem., 16, 2 (1877).

    Google Scholar 

  22. J. Volhard, J. Prakt. Chem. [2] 9, 9 (1874).

    Google Scholar 

  23. A. P. Grishchuk, I. D. Komaritsa, and S. N. Baranov, Khim. Geterotsikl. Soedin., 706 (1966).

  24. M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, and J. A. Montgomery, Jr., J. Comput. Chem. 14, 1347 (1993).

    Google Scholar 

  25. T. H. Dunning, Jr. and P. J. Hay, in Modern Theoretical Chemistry, Plenum Press, New York, 1977, 3.

    Google Scholar 

  26. J. S. Binkley, J. A. Pople, and W. J. Hehre, J. Am. Chem. Soc., 102, 939 (1980).

    Google Scholar 

  27. W. J. Pietro, M. M. Frankl, W. J. Hehre, D. J. DeFrees, J. A. Pople, and J. S. Binkley, J. Am. Chem. Soc., 104, 5039 (1982).

    Google Scholar 

  28. R. Ditchfield, W. J. Hehre, and J. A. Pople, J. Chem. Phys., 54, 724 (1971)

    Google Scholar 

  29. W. J. Hehre and W. A. Latham, J. Chem. Phys., 56, 5255 (1972).

    Google Scholar 

  30. W. J. Hehre, Acc. Chem. Res., 9, 399 (1976).

    Google Scholar 

  31. M. M. Frankl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. De Frees, and J. A. Pople, J. Chem. Phys., 77, 3654 (1982).

    Google Scholar 

  32. P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 28, 213 (1973).

    Google Scholar 

  33. C. Moller and M. S. Plesset, Phys. Rev., 46, 618 (1934).

    Google Scholar 

  34. M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc., 99, 4899 (1977).

    Google Scholar 

  35. M. J. S. Dewar and C. H. Reynolds, J. Comput. Chem., 7, 14 (1986).

    Google Scholar 

  36. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985).

    Google Scholar 

  37. M. J. S. Dewar and Y.-C. Yuan, Inorg. Chem., 29, 3881 (1990).

    Google Scholar 

  38. J. J. P. Stewart, J. Comput. Chem., 10, 209 (1989).

    Google Scholar 

  39. J. J. P. Stewart, MOPAC 6.0: QCPE program 455.

  40. J. Baker, J. Comput. Chem., 7, 385 (1986).

    Google Scholar 

  41. K. Jensen and A. Friediger, Kgl. Danske Videnskab. Selskab. Math-fys. Medd., 20, 1 (1943); Chem. Abstr., 39, 2068 (1945).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Bulgarian Academy of Sciences, 1113, Sofia, Bulgaria

    V. Enchev & B. Jordanov

  2. Faculty of Chemistry, Sofia University, 1126, Sofia, Bulgaria

    S. Chorbadjiev

Authors
  1. V. Enchev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Chorbadjiev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. Jordanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Enchev, V., Chorbadjiev, S. & Jordanov, B. Comparative Study of the Structure of Rhodanine, Isorhodanine, Thiazolidine-2,4-dione, and Thiorhodanine. Chemistry of Heterocyclic Compounds 38, 1110–1120 (2002). https://doi.org/10.1023/A:1021217617954

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1021217617954

Search

Navigation