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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 12, pp 1533–1538 | Cite as

Quantum-chemical investigation of the mechanism of trans-cis photoisomerization of 4-[2-(2-chlorophenyl)vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile

  • D. Jansone
  • M. FleisherEmail author
  • J. Popelis
  • G. Andreeva
  • L. Baumane
  • E. Abele
Article
  • 78 Downloads

A quantum-chemical investigation has been carried out by the semiempirical AM1 method of the trans-cis photoisomerization mechanism of 4-[2-(2-chlorophenyl)vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetra- hydropyridine-3-carbonitrile. It was shown that the isomerization process proceeds in the excited singlet state S1 by rotation of the 2-chlorophenyl substituent around the C(2)–C(3) bond. Electronic absorption spectra of the isomers were calculated by the INDO/S method Transitions caused by exitation of an electron from HOMO to LUMO were characterized by the greatest intensity.

Keywords

4-[2-(2-chlorophenyl)vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile trans-cis photoisomerization semiempirical method AM1 INDO/S MOPAC2009 

Notes

The work was carried out with the financial support of the European Social Fund (project No. 2009/0203/IDP/1.1.1.2.0/09/APIA/VIAA/023).

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Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • D. Jansone
    • 1
  • M. Fleisher
    • 1
    Email author
  • J. Popelis
    • 1
  • G. Andreeva
    • 1
  • L. Baumane
    • 1
  • E. Abele
    • 1
  1. 1.Latvian Institute of Organic SynthesisRigaLatvia

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