Advertisement

Russian Chemical Bulletin

, Volume 62, Issue 8, pp 1871–1876 | Cite as

Crystal structures of pyridinemonocarboxylic acid peroxosolvates

  • A. G. Medvedev
  • A. A. Mikhailov
  • P. V. Prikhodchenko
  • T. A. Tripol’skaya
  • O. Lev
  • A. V. Churakov
Full Articles

Abstract

The crystal structures of new peroxosolvates of the following pyridinemonocarboxylic acids were studied: picolinic 2-C5H4NCOOH·H2O2 (1), nicotinic 3-C5H4NCOOH·H2O2 (2), and isonicotinic 4-C5H4NCOOH·2H2O2 (3). In these compounds, the acids exist exclusively as zwitterions, as opposed to non-solvated crystals. In compounds 13, the hydrogen peroxide molecules form two donor hydrogen bonds and, in some cases, one additional acceptor hydrogen bond. Peroxosolvate 2 can be considered as a novel drug formulation of vitamin B3.

Key words

hydrogen peroxide peroxosolvates pyridinemonocarboxylic acids X-ray diffraction crystal packing hydrogen bonding drug formulation 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    M. V. Marshall, L. P. Cancro, S. L. Fischman, J. Periodontol., 1995, 66, 786.CrossRefGoogle Scholar
  2. 2.
    R. Hage, A. Lienke, Angew. Chem., Int. Ed. (Engl.), 2006, 45, 206.CrossRefGoogle Scholar
  3. 3.
    T. Finkel, N. J. Holbrook, Nature, 2000, 408, 239.CrossRefGoogle Scholar
  4. 4.
    M. J. Davies, Biochim. Biophys. Acta, Proteins Proteomics, 2005, 1703, 93.CrossRefGoogle Scholar
  5. 5.
    G. P. Bienert, J. K. Schjoerring, T. P. Jahn, Biochim. Biophys. Acta, Biomembr., 2006, 1758, 994.CrossRefGoogle Scholar
  6. 6.
    L. Chen, A. Y. Lyubimov, L. Brammer, A. Vrielink, N. S. Sampson, Biochemistry, 2008, 47, 5368.CrossRefGoogle Scholar
  7. 7.
    H. Jakob, S. Leininger, T. Lehmann, S. Jacobi, S. Gutewort, in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005, 26, pp. 293.Google Scholar
  8. 8.
    C. J. Fritchie, R. K. McMullan, Acta Crystallogr., 1981, B37, 1086.CrossRefGoogle Scholar
  9. 9.
    A. G. Medvedev, A. A. Mikhaylov, A. V. Churakov, P. V. Prikhodchenko, O. Lev, Acta Crystallogr. C, 2012, C68, i20.CrossRefGoogle Scholar
  10. 10.
    F. H. Allen, Acta Crystallogr., 2002, B58, 380.CrossRefGoogle Scholar
  11. 11.
    A. V. Churakov, P. V. Prikhodchenko, J. A. K. Howard, O. Lev, Chem. Commun., 2009, 4224.Google Scholar
  12. 12.
    P. V. Prikhodchenko, A. G. Medvedev, T. A. Tripol’skaya, A. V. Churakov, Y. Wolanov, J. A. K. Howard, O. Lev, Cryst. Eng. Commun., 2011, 13, 2399.CrossRefGoogle Scholar
  13. 13.
    T. Khan, J. C. Halle, M. P. Simonnin, R. Schaal, J. Phys. Chem., 1977, 81, 587.CrossRefGoogle Scholar
  14. 14.
    L. M. Schwartz, R. I. Gelb, J. Mumford-Zisk, D. A. Laufer, J. Chem. Soc., Perkin Trans. 2, 1987, 452.Google Scholar
  15. 15.
    P. I. Nagy, K. Takács-Novák, J. Am. Chem. Soc., 1997, 119, 4999.CrossRefGoogle Scholar
  16. 16.
    A. Kutoglu, C. Scheringer, Acta Crystallogr. C, 1983, C39, 232.CrossRefGoogle Scholar
  17. 17.
    F. Takusagawa, A. Shimada, Acta Crystallogr. B, 1976, B32, 1925.CrossRefGoogle Scholar
  18. 18.
    H. Hamazaki, H. Hosomi, S. Takeda, H. Kataoka, S. Ohba, Acta Crystallogr. C, 1998, C54, IUC9800049.Google Scholar
  19. 19.
    A. V. Churakov, P. V. Prikhodchenko, J. A. K. Howard, Cryst. Eng. Commun., 2005, 7, 664.CrossRefGoogle Scholar
  20. 20.
    M. V. Vener, A. G. Medvedev, A. V. Churakov, P. V. Prikhodchenko, T. A. Tripol’skaya, O. Lev, J. Phys. Chem. A, 2011, 115, 13657.CrossRefGoogle Scholar
  21. 21.
    J.-M. Savariault, M. S. Lehmann, J. Amer. Chem. Soc., 1980, 102, 1298.CrossRefGoogle Scholar
  22. 22.
    A. V. Churakov, S. S. Karlov, E. Kh. Lermontova, G. S. Zaitseva, J. A. K. Howard, Acta Crystallogr. C., 2007, C63, o761.CrossRefGoogle Scholar
  23. 23.
    J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem. Int., Ed. Engl., 1995, 34, 1555.CrossRefGoogle Scholar
  24. 24.
    A. L. Gillon, N. Feeder, R. J. Davey, R. Storey, Cryst. Growth Des., 2003, 3, 663.CrossRefGoogle Scholar
  25. 25.
    L. Infantes, L. Fábián, W. D. S. Motherwell, Cryst. Eng. Commun., 2007, 9, 65.CrossRefGoogle Scholar
  26. 26.
    Bol’shaya meditsinskaya entsiklopediya [Great Medical Encyclopedia], Sov. entsiklopediya, Moscow, 1982 (in Russian).Google Scholar
  27. 27.
    Y. Wolanov, O. Lev, A. V. Churakov, A. G. Medvedev, V. M. Novotortsev, P. V. Prikhodchenko, Tetrahedron, 2010, 66, 5130.CrossRefGoogle Scholar
  28. 28.
    W. C. Schumb, C. N. Satterfield, R P. Wentworth, Hydrogen Peroxide, Reinhold publishing corp., New York, 1955.Google Scholar
  29. 29.
    G. M. Sheldrick, SADABS, Program for Scaling and Correction of Area Detector Data, University of Göttingen, Germany, 1997.Google Scholar
  30. 30.
    G. M. Sheldrick, Acta. Crystallogr., 2008, A64, 112.CrossRefGoogle Scholar
  31. 31.
    A. V. Churakov, J. A. K. Howard, Acta Crystallogr. E, 2007, E63, o4483.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • A. G. Medvedev
    • 1
  • A. A. Mikhailov
    • 1
  • P. V. Prikhodchenko
    • 1
  • T. A. Tripol’skaya
    • 1
  • O. Lev
    • 2
  • A. V. Churakov
    • 1
  1. 1.N. S. Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.Casali Institute of Applied Chemistry, Chemistry InstituteHebrew University of JerusalemJerusalemIsrael

Personalised recommendations