Preferences help
enabled [disable] Abstract
Number of results
2003 | 1 | 4 | 356-365
Article title

IR-spectral study of photoinduced tautomerization in 1,3-diphenyl-pyrazol-5-one

Title variants
Languages of publication
The UV-photoinduced prototropic isomerization of 1,3-diphenyl pyrazol-5-one (DPhP) embedded in polyvinyl chloride (PVC) film is studied by means of difference in IR spectral analysis. The initially existing CH-form in non-irradiated compound is transformed to NH-form, and a hydrochloride salt is stabilized because of the photodegradation of the PVC. An additional comparative IR spectral study of DPhP in different solutions as well as of its hydrochloride salts in solid state is also carried out.
Physical description
1 - 12 - 2003
1 - 12 - 2003
  • [1] J. Elguero, C. Marzin, A.R. Katritzky and P. Linda: The tautomerism of Heterocycles, Academic Press, New York, 1976.
  • [2] J. Elguero, A.R. Katritzky and P. Linda: The tautomerism of Heterocycles, Academic Press, New York, 1999.
  • [3] A.R. Katritzky, and A.C. Bolton: Tautomerism of Heterocycles, Suppl. 1, Academic Press, New York, 1976.
  • [4] A.R. Katritzky and F.W. Maine: “The Tautomerism of the heteroaromatic Compounds with Five membered rings”, Tetrahedron, Vol. 20, (1964), pp. 299–314.[Crossref]
  • [5] J. Elguero, R. Jacquier and G. Tarrago: “Recherches la serie des azoles. XXX-Structure des pyrazolones en solution: determination de l'equilibrre et comportement spectral des pyrazolones tautomeres”, Bulletin Soc. Chim. France, (1967), pp. 3780–3794.
  • [6] A. Maquestiau, Y. Van Heverbeke and R. Jacquerye: “Tautomerie dans le serie des pyrazolones. Influence du milien sur l'equilibre prototropique des pyrazoline-5-ones N1 substituents”, Bull. Soc. Chim. Belg, Vol. 82, (1973), pp. 215–231.[Crossref]
  • [7] J. Elguero: Comprehensive Heterocyclic Chemistry. A.R. Katritzky, C.W. Ress (Eds.), Pergamon Press, Oxford, (1984), Vol. 5, p. 167; b) R.N. Butler: Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Ress and E.F.V. Scriven (Eds.), Pergamon Press, Oxford, (1996), Vol 3, p. 1.
  • [8] D. Zeigan, E. Kleinpeter, H. Wilde and G. Mann: “13C NMR-Untersuchung der tautomerie und des substiturntenffrktes 4-substitutierter Pyrazolin-5-one”, Journal f. Praktische Chemie, Vol. 323, (1981), pp. 188–198.[Crossref]
  • [9] T. Nishiwaki and K. Kondo: “Studies on Heterocyclic Chemistry Part XII. Tautomerizm of α-(5-oxo-Δ3-isoxazolin-4-yl)benzylphosphonates”, Journal of Chemical Society, Perkin Transitions I, (1972), pp. 90–92.[Crossref]
  • [10] D.S. Iyengar, K.K. Prasad and R.V. Venkataratnam: “1-Heteroarylpyrazoles. Stabilization of the 5-hydroxy tautomeric form by an a-nitrogen atom and effect on spectral properties”, Tetrahedron Letters, Vol. 37, (1972), pp. 3937–3940.[Crossref]
  • [11] G.A. Newman and P.J.S. Pauwels: “Pyrazolin-5-one tautomerism. II. Effect of 3-substituents”, Tetrahedron, Vol. 26, (1970), pp. 1571–1578[Crossref]
  • [12] C. Dardonvill, J. Elguero, I. Rozas and C. Fernandez-Castano: “Tautomerism of 1-(2′,4′-dinitrophenyl)-3-methyl-2-pyrazolin-5-one: theoretical calculations, solid and solution NMR studies and X-ray crystallography”, New Journal of Chemistry, Vol. 12, (1998), pp. 1421–1430.[Crossref]
  • [13] A. Chapkanov and I. Petkov: “Spectral and photochemical behavior of some pyrazolones in solution, micelles and polymer films”, Analytical Laboratory, Vol. 7, (1988), pp. 143–147.
  • [14] J. Maack, R.C. Ahuja, D. Mobius, H. Tachibana H and M. Matsumoto: “Molecular cis-trans switching in amphiphilic monolayers containing azobenzene moieties”, Thin Solid Films, Vol. 242, (1994), pp. 122–126.[Crossref]
  • [15] F. Chick and N.T.M. Wilsmore: “Acetylketen: a Polymeride of Keten”, Journal of the Chemical Society, Vol. 93, (1908), pp. 946–950.
  • [16] M.G. Arnaudov: “The influence of the medium on the infrared spectrum of selfassociated systems”, Internet Journal of Vibrational Spectroscopy, Vol. 5, (2001), section 3.
  • [17] G. Varsanyi: Vibrational spectra of benzene derivatives, Akademia Kiado, Budapest, 1969.
  • [18] M. Arnaudov and Y. Dimitriev: “Study of the structural transition in binary tellurite glasses by means of reduced infrared spectra”, Phys. Chem. Glasses, Vol. 42, (2001) pp. 99–102.
  • [19] E. Spiner: “The Vibration Spectra and Structures of the Hydrochlorides of Aminopyridines”, Journal of Chemical Society, Vol. 3, (1962) pp. 3119–3126.[Crossref]
Document Type
Publication order reference
YADDA identifier
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.