Table of Contents Author Guidelines Submit a Manuscript
Journal of Spectroscopy
Volume 2013, Article ID 197475, 12 pages
http://dx.doi.org/10.1155/2013/197475
Research Article

Synthesis and Conformational Assignment of N-(E)-Stilbenyloxymethylenecarbonyl-Substituted Hydrazones of Acetone and o-(m- and p-) Chloro- (nitro-) benzaldehydes by Means of and NMR Spectroscopy

Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

Received 29 June 2012; Revised 17 October 2012; Accepted 31 October 2012

Academic Editor: Ozlem Oter

Copyright © 2013 Przemysław Patorski et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. P. Vicini, F. Zani, P. Cozzini, and I. Doytchinova, “Hydrazones of 1,2-benzisothiazole hydrazides: synthesis, antimicrobial activity and QSAR investigations,” European Journal of Medicinal Chemistry, vol. 37, no. 7, pp. 553–564, 2002. View at Publisher · View at Google Scholar · View at Scopus
  2. G. Turan-Zitouni, Y. Blache, and K. Güven, “Synthesis and antimicrobial activity of some imidazo-[1,2-a]pyridine-2-carboxylic acid arylidenehydrazide derivatives,” Bollettino Chimico Farmaceutico, vol. 140, no. 6, pp. 397–400, 2001. View at Google Scholar
  3. S. Takaji, H. Hibasami, I. Imoto et al., “Growth inhibition of Helicobacter pylori by a polyamine synthesis inhibitor, methylglyoxal bis(cyclopentylamidinohydrazone),” Letters in Applied Microbiology, vol. 25, no. 3, pp. 177–180, 1997. View at Google Scholar · View at Scopus
  4. B. N. Dobrova, A. S. Dimoglo, and Y. M. Chumakov, “Study of the relationship between chemical structure and antimicrobial activity in a series of hydrazine-based coordination compounds,” Drug Research, vol. 50, no. 8, pp. 747–751, 2000. View at Google Scholar
  5. V. M. Naik and N. B. Mallur, “Synthesis and characterization of niobium(V) complexes with terdentate ONO donor hydrazones,” Indian Journal of Chemistry A, vol. 41, no. 4, pp. 780–784, 2002. View at Google Scholar · View at Scopus
  6. P. Domiano, C. Pelizzi, G. Predieri, C. Vignalli, and G. Palla, “Aroylhydrazones as chelating agents: d10-metal complexes of pyridine-2-carbaldehyde salicyloylhydrazone and x-ray structure of the zinc derivative,” Polyhedron, vol. 3, no. 3, pp. 281–286, 1984. View at Google Scholar · View at Scopus
  7. M. Gallego, M. Garcia-Vargas, and M. Valcarcel, “Pyridine-2-carbaldehyde 2-hydroxybenzoylhydrazone as a selective reagent for the extraction and spectrophotometric determination of iron(II),” The Analyst, vol. 104, no. 1239, pp. 613–619, 1979. View at Google Scholar
  8. A. Casoli, A. Mangia, and G. Predieri, “Determination of uranium by reversed-phase high-performance liquid chromatography,” Analytical Chemistry, vol. 57, no. 2, pp. 561–563, 1985. View at Google Scholar
  9. P. R. Mandlik, S. R. Aswale, and A. S. Aswar, “Chromium(III), manganese(III), iron(III), oxovanadium(II), zirconium(IV) and dioxouranium(II) complexes of hydrazone of isonicotinic acid hydrazide,” Journal of the Indian Chemical Society, vol. 79, no. 8, pp. 689–692, 2002. View at Google Scholar · View at Scopus
  10. C. Glidewell, J. N. Low, J. M. S. Skakle, and J. L. Wardell, “Hydrogen-bonded dimers in 2-nitrobenzaldehyde hydrazone and a three-dimensional hydrogen-bonded framework in 3-nitrobenzaldehyde hydrazone,” Acta Crystallographica Section C, vol. 60, no. 9, pp. o686–o689, 2004. View at Publisher · View at Google Scholar · View at Scopus
  11. C. Glidewell, J. N. Low, J. M. S. Skakle, and J. L. Wardell, “Hydrogen bonding in nitroaniline analogues: 4-nitrobenzaldehyde hydrazone forms hydrogen-bonded sheets of R44(26) rings,” Acta Crystallographica C, vol. 60, no. 1, pp. o33–o34, 2004. View at Publisher · View at Google Scholar · View at Scopus
  12. A. V. Shastin, V. N. Korotchenko, V. G. Nenajdenko, and E. S. Balenkova, “A novel synthetic approach to dichlorostyrenes,” Tetrahedron, vol. 56, no. 35, pp. 6557–6563, 2000. View at Google Scholar · View at Scopus
  13. V. Z. Shirinian, L. I. Belen'kii, and M. M. Krayushkin, “A convenient method for the preparation of N-unsubstituted hydrazones of aromatic ketones and aldehydes,” Russian Chemical Bulletin, vol. 48, no. 11, pp. 2171–2172, 1999. View at Google Scholar · View at Scopus
  14. H. Schmidt, “Indigo—100 jahre industrielle synthese,” Chemie in Unserer Zeit, vol. 31, no. 3, pp. 121–128, 1997. View at Google Scholar · View at Scopus
  15. P. Šebej, T. Šolomek, L. Hroudná, P. Brancová, and P. Klán, “Photochemistry of 2-nitrobenzylidene acetals,” Journal of Organic Chemistry, vol. 74, no. 22, pp. 8647–8658, 2009. View at Publisher · View at Google Scholar · View at Scopus
  16. G. Bielek and H. Kindl, Österreichische Chemiker-Zeitung, vol. 63, pp. 273–281, 1962.
  17. T. P. Schultz, T. F. Hubbard, L. Jin, T. H. Fisher, and D. D. Nicholas, “Role of stilbenes in the natural durability of wood: fungicidal structure-activity relationships,” Phytochemistry, vol. 29, no. 5, pp. 1501–1507, 1990. View at Google Scholar · View at Scopus
  18. T. P. Schultz, W. D. Boldin, T. H. Fisher, D. D. Nicholas, K. D. Mcmurtrey, and K. Pobanz, “Structure-fungicidal properties of some 3- and 4-hydroxylated stilbenes and bibenzyl analogues,” Phytochemistry, vol. 31, no. 11, pp. 3801–3806, 1992. View at Google Scholar · View at Scopus
  19. S. Renaud and M. De Lorgeril, “Wine, alcohol, platelets, and the French paradox for coronary heart disease,” The Lancet, vol. 339, no. 8808, pp. 1523–1526, 1992. View at Publisher · View at Google Scholar · View at Scopus
  20. J.-R. Dai, Y. F. Hallock, J. H. Cardellina II, and M. R. Boyd, “HIV-inhibitory and cytotoxic oligostilbenes from the leaves of Hopea malibato,” Journal of Natural Products, vol. 61, no. 3, pp. 351–353, 1998. View at Publisher · View at Google Scholar
  21. E. Wyrzykiewicz and D. Prukała, “New isomeric N-substituted hydrazones of 2-, 3-and 4-pyridinecarboxaldehydes,” Journal of Heterocyclic Chemistry, vol. 35, no. 2, pp. 381–387, 1998. View at Google Scholar · View at Scopus
  22. E. Wyrzykiewicz and A. Blaszczyk, “New isomeric N-substituted hydrazones of 2-, 3- and 4-pyridinecarboxaldehydes and methyl-3-pyridylketone,” Journal of Heterocyclic Chemistry, vol. 37, no. 4, pp. 975–981, 2000. View at Google Scholar · View at Scopus
  23. E. Wyrzykiewicz, A. Blaszczyk, and I. Turowska-Tyrk, “N-(E)-2-stilbenyloxymethylenecarbonyl substituted hydrazones of ortho, meta and para hydroxybenzaldehydes,” Bulletin of the Polish Academy of Sciences, vol. 48, no. 3, pp. 213–229, 2000. View at Google Scholar
  24. E. Wyrzykiewicz and D. Prukała, “New isomeric N-substituted hydrazones of ortho, meta and para hydroxybenzaldehydes,” Polish Journal of Chemistry, vol. 72, no. 4, pp. 694–702, 1998. View at Google Scholar · View at Scopus
  25. E. Wyrzykiewicz and D. Prukała, “EIMS study of new isomeric N-substituted hydrazones of 2-(3- and 4-)- pyridinecarboxaldehydes,” Journal of Heterocyclic Chemistry, vol. 36, no. 3, pp. 739–745, 1999. View at Google Scholar · View at Scopus
  26. E. Wyrzykiewicz and D. Prukala, “Electron impact-induced mass spectral study of new isomeric N-substituted hydrazones of ortho-, meta- and para-hydroxybenzaldehydes,” European Journal of Mass Spectrometry, vol. 5, no. 3, pp. 183–190, 1999. View at Google Scholar
  27. G. Palla, G. Predieri, P. Domiano, C. Vignali, and W. Turner, “Conformational behaviour and E/Z isomerization of N-acyl and N-aroylhydrazones,” Tetrahedron, vol. 42, no. 13, pp. 3649–3654, 1986. View at Google Scholar · View at Scopus
  28. E. A. Braude, “Studies in light absorption. Part VIII. Dibenzyl and stilbene derivatives. Interaction between unconjugated chromophores,” Journal of the Chemical Society, pp. 1902–1909, 1949. View at Google Scholar
  29. M. Calvin and H. Ward Alter, “Substituted stilbenes. I. absorption spectra,” The Journal of Chemical Physics, vol. 19, no. 6, pp. 765–767, 1951. View at Google Scholar
  30. D. F. Detar and L. A. Carpino, “The preparation of and the spectral characteristics of some 2-substituted cis- and trans-stilbenes,” Journal of the American Chemical Society, vol. 78, no. 2, pp. 475–479, 1956. View at Google Scholar
  31. M. Oki and H. Kunimoto, “The characteristic infrared absorption bands of cis-stilbene and its p,p'-disubstituted derivatives,” Spectrochimica Acta, vol. 19, no. 9, pp. 1463–1471, 1963. View at Google Scholar
  32. H. Shanan-Atidi and K. H. Bar-Eli, “A convenient method for obtaining free energies of activation by the coalescence temperature of an unequal doublet,” Journal of Physical Chemistry, vol. 74, no. 4, pp. 961–963, 1970. View at Google Scholar · View at Scopus
  33. G. Palla, C. Pelizzi, G. Predieri, and C. Vignali, Gazzetta Chimica Italiana, vol. 112, p. 339, 1982.
  34. E. Wyrzykiewicz, J. Kępka, and W. Prukała, Polish Journal of Chemistry, vol. 62, pp. 251–255, 1988.
  35. E. Wyrzykiewicz, Annales Societatis Chimicae Polonorum, vol. 42, pp. 347–351, 1968.