Chemistry of Heterocyclic Compounds

, Volume 21, Issue 6, pp 680–684 | Cite as

X-ray diffraction and spectral studies of 1-phenyl-3-methyl-4-(2′,4′-Dimethylphenylazo)-pyrazolone-5

  • L. G. Kuz'mina
  • L. P. Grigor'eva
  • Yu. T. Struchkov
  • Z. I. Ezhkova
  • B. E. Zaitsev
  • V. A. Zaitseva
  • P. P. Pron'kin
Article
  • 39 Downloads

Abstract

The molecular and crystal structures of 1-phenyl-3-methyl-4-(2′,4′-dimethyl-phenylazo) pyrazolone-5 were determined. In the crystal the molecule exists as the hydrazone tautomer. The pyrazole ring is planar, and the substituents are practically coplanar with it. The molecule contains an intramolecular NH...O hydrogen bond that closes a practically planar six-membered ring (N...O, 2.77 (I), H...O 2.14 Å, angle at H(N(4)) hydrogen 131 °). The x-ray diffraction data agree with the spectral data and with the CNO calculation.

Keywords

Hydrogen Crystal Structure Hydrogen Bond Organic Chemistry Spectral Data 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    W. Pelz, W. Pushel, H. Schellenberger, and K. Loffer, Angew, Chem., 72, 967 (1960).Google Scholar
  2. 2.
    J. Ilgnero, R. Jacgner [sic], and G. Farrago, Bull. Soc. Chim. Fr., 2990 (1966).Google Scholar
  3. 3.
    J. R. Jones, A. J. Ryan, S. Sternhell, and S. E. Wright, Tetrahedron, 19, 1497 (1960).Google Scholar
  4. 4.
    F. A. Snavely and C. H. Joder, J. Org. Chem., 33, 513 (1968).Google Scholar
  5. 5.
    B. E. Zaitsev, V. A. Zaitseva, A. K. Molodkin, and E. S. Obraztsova, Zh. Neorg. Khim., 24, 127 (1979).Google Scholar
  6. 6.
    B. E. Zaitsev and Yu. N. Sheinker, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, No. 3, 407 (1963).Google Scholar
  7. 7.
    E. Bayer and G. Hafelinger, Chem. Ber., 99, 1689 (1966).Google Scholar
  8. 8.
    H. L. Ammon, P. M. Marroechi, M. C. Regan, and E. Colicelli, Acta Crystallogr. B, 35, 1722 (1979).Google Scholar
  9. 9.
    L. E. Sutton (editor), Tables of Interatomic Distances and Configuration in Molecules and Ions, Special Publ. No. 18, Chemical Society (1965).Google Scholar
  10. 10.
    Douglas L. Smith and Eileen K. Barrett, Acta Crystallogr. B, 27, 2043 (1971).Google Scholar
  11. 11.
    M. Dewar, Molecular Orbital Theory of Organic Chemistry, McGraw-Hill (1969).Google Scholar
  12. 12.
    D. A. Ramsay, J. Am. Chem. Soc., 72, 74 (1952).Google Scholar

Copyright information

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • L. G. Kuz'mina
    • 1
    • 2
  • L. P. Grigor'eva
    • 1
    • 2
  • Yu. T. Struchkov
    • 1
    • 2
  • Z. I. Ezhkova
    • 1
    • 2
  • B. E. Zaitsev
    • 1
    • 2
  • V. A. Zaitseva
    • 1
    • 2
  • P. P. Pron'kin
    • 1
    • 2
  1. 1.Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow
  2. 2.Scientific-Research Institute for Organic Intermediates and DyesMoscow

Personalised recommendations