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Acid-Base Properties and Prototropic Tautomerism of Isomeric 1,2,4-Triazin-3- and -5-ones

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Abstract

The acidity and basicity constants of isomeric phenyl(aryl)-1,2,4-triazin-3- and -5-ones in aqueous solution were determined by spectrophotometry: pK a = 7.3–6.2; pK BH+= 0.1 to –2.2. 1,2,4-Triazin-3-ones are weaker bases than the corresponding 1,2,4-triazin-5-ones. According to the AM1 calculations, the most thermodynamically favorable tautomer in the gas phase is the oxo form: namely, 2H-tautomers of the neutral bases and 2,4-H,H +-tautomers of the conjugate acids.

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REFERENCES

  1. Gilchrist, T.L., Heterocyclic Chemistry, Harlow, Essex, England: Longman Scientific & Technical, 1992, 2nd ed.

    Google Scholar 

  2. Kleemann, A., Engel, J., Kutscher, B., and Reichert, D., Pharmaceutical Substances, New York: Georg Thieme, 1999.

    Google Scholar 

  3. Pozharskii, A.F. and Soldatenko, A.T., Molekuly-perstni (Finger-Ring Molecules), Moscow: Khimiya, 1993.

    Google Scholar 

  4. Katritzky, A.R., Karelson, M., and Malhotra, N., Heterocycles, 1991, vol. 32, p. 127.

    Google Scholar 

  5. Elguero, J., Marzin, C., Katritzky, A.R., and Linda, P., The Tautomerism of Heterocycles, New York: Academic, 1976.

    Google Scholar 

  6. Daunis, J., Djouai-Hifdi, L., and Pigiere, C., Org. Mass. Spectrom., 1981, vol. 16, p. 347.

    Google Scholar 

  7. Lee, J.K., Park, M.D., Lee, D.Y., and Kim, W.S., Tachan Hwahakhoe Chin., 1988, vol. 32, p. 385; Chem. Abstr., 1989, vol. 110, no. 95 171 h.

    Google Scholar 

  8. Dieckmann, H., Kreuzing, R., and Bahadir, M., J. Anal. Chem., 1994, vol. 348, p. 749.

    Google Scholar 

  9. Bird, C.W., Heterocycles, 1994, vol. 37, p. 249.

    Google Scholar 

  10. Nalepa, K., Halama, A., Nevecna, T., and Bekarek, V., Collect. Czech. Chem. Commun., 1995, vol. 60, p. 251.

    Google Scholar 

  11. Pitha, J., Fiedler, P., and Gut, J., Collect. Czech. Chem. Commun., 1966, vol. 31, p. 1864.

    Google Scholar 

  12. Gut, J., Jonas, J., and Pitha, J., Collect. Czech. Chem. Commun., 1964, vol. 29, p. 1394.

    Google Scholar 

  13. Katritzky, A.R., Karelson, M., and Harris, P.A., Heterocycles, 1991, vol. 32, p. 329.

    Google Scholar 

  14. Albro, P.W., Parker, C.A., Abusteit, E.O., Mester, T.C., Hass, J.R., Sheldon, Y., and Corbin, F.T., J. Agric. Food. Chem., 1984, vol. 32, p. 212.

    Google Scholar 

  15. Maslowska, J. and Jaroszynska, J., Pol. J. Chem., 1987, vol. 61, p. 827.

    Google Scholar 

  16. Alekseeva, I.V., Shalamai, A.S., Sidorenko, E.G., and Chernetskii, V.P., Ukr. Khim. Zh., 1979, vol. 45, p. 48.

    Google Scholar 

  17. Chapman and Hall Combined Dictionary of Organic Compounds, New York: Wiley, 1983, vol. 5.

  18. Bacaloglu, R., Bacaloglu, I., and Simon, Z., Rev. Roum. Chem., 1992, vol. 37, p. 819.

    Google Scholar 

  19. Brinck, T., Murray, J.S., Politzer, P., and Carter, R.E., J. Org. Chem., 1991, vol. 56, p. 2934.

    Google Scholar 

  20. Rao, P. and Benner, S.A., J. Org. Chem., 2001, vol. 66, p. 5012.

    Google Scholar 

  21. Ostrovskii, V.A., Erusalimskii, G.B., and Shcherbinin, M.B., Zh. Org. Khim., 1993, vol. 29, p. 1297.

    Google Scholar 

  22. Andrianov, V.G., Shokhen, M.A., and Eremeev, A.V., Khim. Geterotsikl. Soedin., 1989, p. 508.

  23. Shaffer, A.A. and Wierschke, S.G., J. Comput. Chem., 1993, vol. 14, p. 75.

    Google Scholar 

  24. Turchaninov, V.K. and Eroshchenko, S.V., J. Mol. Struct. (Theochem), 1992, vol. 85, p. 371.

    Google Scholar 

  25. Trifonov, R.E., Cand. Sci. (Chem.) Dissertation, St. Petersburg, 1998.

  26. Trifonov, R.E., Ivanova, S.E., Ostrovskii, V.A., and Koldobskii, G.I., Zh. Org. Khim., 1994, vol. 30, p. 1556.

    Google Scholar 

  27. Ostrovskii, V.A. and Koldobskii, G.I., Slabye organicheskie osnovaniya (Weak Organic Bases), Leningrad: Leningr. Gos. Univ., 1990.

    Google Scholar 

  28. Bershtein, I.Ya. and Kaminskii, Yu.L., Spektrofotometricheskii analiz v organicheskoi khimii (Spectrophotometric Analysis in Organic Chemistry), Leningrad: Khimiya, 1986.

    Google Scholar 

  29. Trifonov, R.E., Rtishchev, N.I., and Ostrovskii, V.A., Spectrochim. Acta, Part A, 1996, vol. 52, p. 1875.

    Google Scholar 

  30. Cox, R.A. and Yates, K., Can. J. Chem., 1983, vol. 61, p. 2225.

    Google Scholar 

  31. Perrin, D.D., Aust. J. Chem., 1963, vol. 16, p. 572.

    Google Scholar 

  32. Vinot, N. and M'Packo, J., C. R. Acad. Sci., Ser. C, 1970, vol. 270, p. 1042.

    Google Scholar 

  33. M'Packo, J.-P. and Vinot, N., Bull. Soc. Chim. Fr., 1972, vol. 12, p. 4637.

    Google Scholar 

  34. Lalezari, I. and Golgolab, H., J. Heterocycl. Chem., 1970, vol. 7, p. 689.

    Google Scholar 

  35. Neunhoeffer, H., Reichel, D., Cullman, B., and Rehn, I., Justus Liebigs Ann. Chem., 1990, vol. 776, p. 631.

    Google Scholar 

  36. Kozhevnikov, D.N., Nikitina, T.N., Rusinov, V.L., and Chupakhin, O.N., Mendeleev Commun., 2000, no. 3, p. 117.

  37. Neunhoeffer, H. and Boehnisch, V., Justus Liebigs Ann. Chem., 1976, no. 1, p. 153.

  38. Stewart, J.J.P., MOPAC 6.0, QCPE Program 455, Bloomington, IN, 1990.

  39. Poplavskaya, Yu.V., Trifonov, R.E., Shcherbinin, M.B., and Koldobskii, G.I., Russ. J. Org. Chem., 2000, vol. 6, p. 1788.

    Google Scholar 

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    I. V. Khabibulina, R. E. Trifonov, A. P. Volovodenko, M. S. Eremenkova, O. N. Chupakhin, V. L. Rusinov, G. V. Zyryanov & V. A. Ostrovskii

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  1. I. V. Khabibulina
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  2. R. E. Trifonov
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  3. A. P. Volovodenko
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  4. M. S. Eremenkova
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  5. O. N. Chupakhin
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  6. V. L. Rusinov
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  7. G. V. Zyryanov
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  8. V. A. Ostrovskii
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Khabibulina, I.V., Trifonov, R.E., Volovodenko, A.P. et al. Acid-Base Properties and Prototropic Tautomerism of Isomeric 1,2,4-Triazin-3- and -5-ones. Russian Journal of Organic Chemistry 40, 426–430 (2004). https://doi.org/10.1023/B:RUJO.0000034984.18435.ea

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  • DOI: https://doi.org/10.1023/B:RUJO.0000034984.18435.ea

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