Advertisement

Journal of Structural Chemistry

, Volume 50, Issue 4, pp 722–726 | Cite as

Photoinduced isomerization of 4-(4′-dimethylaminostyryl) pyridine N-oxide

  • A. P. Kondratieva
  • N. Sh. Lebedeva
  • Yu. A. Gubarev
  • N. A. Pavlycheva
  • V. P. Andreev
  • G. A. Alper
  • R. S. Kumeev
Proceedings of the XIV Seminar on Intermolecular Interactions and Molecule Conformations
  • 80 Downloads

Abstract

The effects of photoirradiation on the conformation state of 4-(4′-dimethylaminostyryl)pyridine N-oxide was studied by spectral (EAS, 1H NMR, IR) and thermochemical methods. Transcis isomerization was found to proceed in 4-(4′-dimethylaminostyryl)pyridine N-oxide irradiated with light (λ ≤ 400 nm) in chloroform. The conversion of the trans form of 4-(4′-dimethylaminostyryl)pyridine N-oxide to the cis form depends on the time and intensity of irradiation. Maximum conversion was achieved when a photostationary mixture formed with a ratio of components trans:cis = 40:60. Further irradiation of the solutions of 4-(4′-dimethylaminostyryl)pyridine N-oxide in chloroform led to salification with HCl formed during the decomposition of CHCl3.

Keywords

4-(4′-dimethylaminostyryl)pyridine N-oxide photoirradiation transcis isomerization photostationary mixture 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    O. Kikuchi, M. Azuki, Y. Inadomi, and K. Morihashi, J. Mol. Struct. (Theochem), 468, 95–104 (1999).CrossRefGoogle Scholar
  2. 2.
    H. Kunkely and A. Vogler, J. Photochem. Photobiol. A: Chem., 103, 227–229 (1997).CrossRefGoogle Scholar
  3. 3.
    K. Takeshita, N. Hirota, and M. Terazima, ibid., 134, 103–109 (2000).CrossRefGoogle Scholar
  4. 4.
    H. Gorner, ibid., 126, 15–21 (1999).CrossRefGoogle Scholar
  5. 5.
    V. V. Prezhdo, E. V. Vashchenko, and O. V. Prezhdo, Zh. Obshch. Khim., 70, No. 1, 128–136 (2000).Google Scholar
  6. 6.
    S. P. Ponomarenko, Yu. Ya. Borovikov, G. S. Borovikova, et al., Ukr. Khim. Zh., 59, No. 8, 883–888 (1993).Google Scholar
  7. 7.
    G. D. Titskii and M. K. Turovskaya, USSR Inventor’s Certificate No. 1599366, Byull. Izobret. (1990).Google Scholar
  8. 8.
    Ivashevskaja S.N., Aleshina L.A., Andreev V.P. et al., Acta Crystallogr., 59, 1006–1008 (2003).Google Scholar
  9. 9.
    T. A. Fayed, J. Photochem. Photobiol. A: Chem., 121, 17–25 (1999).CrossRefGoogle Scholar
  10. 10.
    R. M. Silverstein, G. C. Bassler, and T. C. Morrill, Spectrometric Identification of Organic Compounds, Wiley, New York (1981).Google Scholar
  11. 11.
    V. P. Andreev, E. G. Batotsyrenova, A. V. Ryzhakov, and L. L. Rodina, Khim. Geterotsikl. Soedin., No. 8, 1093–1102 (1998).Google Scholar
  12. 12.
    A. S. Dneprovskii and T. I. Temnikova, Theoretical Principles of Organic Chemistry [in Russian], Khimiya, Leningrad (1991).Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2009

Authors and Affiliations

  • A. P. Kondratieva
    • 1
  • N. Sh. Lebedeva
    • 1
  • Yu. A. Gubarev
    • 1
  • N. A. Pavlycheva
    • 1
  • V. P. Andreev
    • 2
  • G. A. Alper
    • 1
  • R. S. Kumeev
    • 1
  1. 1.Institute of Solution ChemistryRussian Academy of SciencesIvanovoRussia
  2. 2.Petrozavodsk State UniversityPetrozavodskRussia

Personalised recommendations