QUANTUM-CHEMICAL INVESTIGATION OF THE MECHANISM OF <i>trans-cis</i> PHOTOISOMERIZATION OF 4-[2-(2-CHLOROPHENYL)VINYL]-6,6-DIMETHYL-2-OXO-1,2,5,6-TETRAHYDROPYRIDINE-3-CARBONITRILE

Authors

  • Д. Янсоне Latvian Institute of Organic Synthesis
  • М. Флейшер Latvian Institute of Organic Synthesis
  • Ю. Попелис Latvian Institute of Organic Synthesis
  • Г. Андреева Latvian Institute of Organic Synthesis
  • Л. Баумане Latvian Institute of Organic Synthesis
  • Э. Абеле Latvian Institute of Organic Synthesis

DOI:

https://doi.org/10.1007/1323

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

Abstract

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-tetrahydropyridine-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.

Authors: D. Jansone, M. Fleisher, J. Popelis, G. Andreeva, L. Baumane, and E. Abele.

English translation in Chemistry of Heterocyclic Compounds, 2011, 47 (12), pp 1533-1538

http://link.springer.com/article/10.1007/s10593-012-0944-z

 

Downloads

Published

2013-12-06

Issue

No. 12 (2011)

Section

Original Papers