Russian Journal of General Chemistry

, Volume 83, Issue 7, pp 1376–1382 | Cite as

Synthesis, structure, and properties of a new phosphorus-containing Schiff’s base, a derivative of pyrazole-5-one

  • L. D. Popov
  • S. A. Borodkin
  • I. N. Scherbakov
  • Yu. N. Tkachenko
  • G. G. Aleksandrov
  • S. S. Beloborodov
  • A. A. Zubenko
  • V. A. Kogan
  • O. V. Maevskii
Article

Abstract

A new Schiff’s base and its salt have been prepared from 2-aminophenyl(triphenyl)phosphonium chloride and 5-hydroxy-3-methyl-1-phenyl-4-formylpyrazole. The products structures have been proved by IR, 1H NMR, and UV spectroscopy, mass spectrometry, X-ray diffraction analysis, and quantum-chemical modeling. Possible tautomerism and some properties of the products have been studied.

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References

  1. 1.
    Minbaev, B.U., Shiffovy osnovaniya (Schiff’s Bases), Alma-Ata: Nauka, 1989.Google Scholar
  2. 2.
    Garnovskii, A.D., Nivorozhkin, A.L., and Minkin, V.I., Coord. Chem. Rev., 1993, vol. 126, nos. 1–2, pp. 1–69.CrossRefGoogle Scholar
  3. 3.
    Garnovskii, A.D., Burlov, A.S., Vasilchenko I.G., Garnovskii, D.A., Uraev, A.I., and Sennikova, E.V., Russ. J. Coord. Chem., 2010, vol. 36, no. 2, pp. 81–96.CrossRefGoogle Scholar
  4. 4.
    Garnovskii, A.D., Sadimenko, A.P., Vasilchenko, I.S., Sennikova, E.V., and Minkin, V.I., Adv. Heterocycl. Chem., 2009, vol. 97, pp. 291–392.CrossRefGoogle Scholar
  5. 5.
    Garnovskii, A.D., and Vasilchenko, I.S., Russ. Chem. Rev., 2005, vol. 74, no. 3, pp. 193–215.CrossRefGoogle Scholar
  6. 6.
    Garnovskii, A.D., Russ. J. Coord. Chem., 1993, vol. 19, no. 5, pp. 368–382.Google Scholar
  7. 7.
    Vigato, P.A. and Tamburini, S., Coord. Chem. Rev., 2004, vol. 248, nos. 17–20, pp. 1717–2128.CrossRefGoogle Scholar
  8. 8.
    Parr, J. and Slawin, A.M.Z., Inorg. Chim. Acta., 2000, vol. 303, no. 1, pp. 116–120.CrossRefGoogle Scholar
  9. 9.
    Shi, P.-Y. and Liu, Y.-H., Organometallics, 2002, vol. 21, no. 15, pp. 3203–3207.CrossRefGoogle Scholar
  10. 10.
    Korupoju, S.R., Lai, R.-Y., Liu, Y.-H., Peng, S.-M., and Liu, S.-T., Inorg. Chim. Acta., 2005, vol. 358, no. 11, pp. 3003–3008.CrossRefGoogle Scholar
  11. 11.
    Doherty, S., Knight, J.G., Scanlan, T.H., Elsegood, R.Y., and Clegg, W., J. Organometal. Chem., 2002, vol. 650, nos. 1–2, pp. 231–248.CrossRefGoogle Scholar
  12. 12.
    Dalili, S., Caiazzo, A., and Yudin A.K., J. Organometal. Chem., 2004, vol. 689, no. 22, pp. 3604–3611.CrossRefGoogle Scholar
  13. 13.
    Faller, J.W., Mason, G., and Parr, J., J. Organometal. Chem., 2002, vol. 650, nos. 1–2, pp. 181–187.Google Scholar
  14. 14.
    Cameron, P.A., Gibson, V.C., Redshaw, C., Segal, J.A., White, J.P., and Williams, D.J., J. Chem. Soc., Dalton Trans., 2002, vol. 2, no. 3, pp. 415–422.CrossRefGoogle Scholar
  15. 15.
    Bhattacharyya, P., Loza, M.L., Parr, J., and Slawin, A.M.Z., J. Chem. Soc., Dalton Trans., 1999, no. 17, pp. 2917–2922.Google Scholar
  16. 16.
    Dilworth, J.R., Howe, S.D., Hutson, A.J., Miller, J.R., Silver, J., Thompson, R.M., Harman, M., and Hursthouse, M.B., J. Chem. Soc., Dalton Trans., 1994, no. 24, pp. 3553–3562.Google Scholar
  17. 17.
    Bhattacharyya, P., Parr, J., and Slawin, A.M.Z., J. Chem. Soc., Dalton Trans., 1998, no. 21, pp. 3609–3614.Google Scholar
  18. 18.
    Amarasekara, A.S., Owereh, O.S., Lysenko, K.A., and Timofeeva, T.V., J. Struct. Chem., 2009, vol. 50, no. 6, pp. 1159–1165.CrossRefGoogle Scholar
  19. 19.
    Kvitko A.Ya. and Porai-Koshits, B.A., Russ. J. Org. Chem., 1966, vol. 11, no. 1, p. 3005.Google Scholar
  20. 20.
    Surati, K.R., Thaker, B.T., and Shan, G.R., Synth. React. Inorg. Metal-Org. and Nano-Metal Chem., 2008, vol. 38, no. 3, pp. 272–279.Google Scholar
  21. 21.
    Raj, D.S., Parmar, N.J., and Shah, J.R., Synth. React. Inorg. Metal-Org. and Nano-Metal Chem., 2004, vol. 34, no. 4, pp. 697–711.CrossRefGoogle Scholar
  22. 22.
    Jadeja, R.N., Shah, J.R., Suresh, E., and Paul, P., Polyhedron, 2004, vol. 23, no. 18, pp. 2465–2474.CrossRefGoogle Scholar
  23. 23.
    Thaker, B.T., Surati, K.R., and Modi, C.K., Russ. J. Coord. Chem., 2008, vol. 34, no. 1, pp. 25–33.CrossRefGoogle Scholar
  24. 24.
    Mashkovskii, M.D., Lekarstvennye sredstva (Pharmaceuticals), Moscow: Meditsina, 1998, p. 1.Google Scholar
  25. 25.
    Popov, L.D., Borodkin, S.A., Shcherbakov, I.N., Tkachenko, Yu.N., and Kogan, V.A., Russ. J. Gen. Chem., 2008, vol. 78, no. 4, pp. 567–574CrossRefGoogle Scholar
  26. 26.
    Casas, J.S., Garcia-Tasende, M.S., Sanchez, A., Sordo, J., and Touceda, A., Coord. Chem. Rev., 2007, vol. 251, nos. 11–12, pp. 1561–1589.CrossRefGoogle Scholar
  27. 27.
    Stephens, P.J., Devlin, F.J., Chabalowski, C.F., and Frisch, M.J., J. Phys. Chem., 1994, vol. 98, no. 45, pp. 11623–11627.CrossRefGoogle Scholar
  28. 28.
    Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, pp. 5648–5652.CrossRefGoogle Scholar
  29. 29.
    Lee, C., Yang, W.,and Parr, R.G., Phys. Rev. (B)., 1988, vol. 37, no. 2, pp. 785–789.CrossRefGoogle Scholar
  30. 30.
    Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Vreven Jr., T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., GAUSSIAN 03, Revision D.01, Gaussian, Inc., Wallingford CT, 2004.Google Scholar
  31. 31.
    Porai-Koshits, B.A. and Kvitko, I.Ya., Russ. J. Org. Chem., 1962, vol. 32, no. 12, p. 4050.Google Scholar
  32. 32.
    Cooper, M.K., Downes, J.M., Duckworth, P.A., and Tiekins, E.R.T., Austral. J. Chem., 1992, vol. 45, no. 3, pp. 595–609.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • L. D. Popov
    • 1
  • S. A. Borodkin
    • 1
  • I. N. Scherbakov
    • 1
  • Yu. N. Tkachenko
    • 1
  • G. G. Aleksandrov
    • 2
  • S. S. Beloborodov
    • 1
  • A. A. Zubenko
    • 3
  • V. A. Kogan
    • 1
  • O. V. Maevskii
    • 1
  1. 1.Southern Federal UniversityRostov-on-DonRussia
  2. 2.Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussia
  3. 3.North-Caucasian Regional Research Veterinary InstituteNovocherkasskRussia

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