In-solution and on-plate light-catalyzed E/Z isomerization of cyclic chalcone analogues. Lipophilicity of F- and Z-2-(X-benzylidene)-1-benzosuberones

P. Perjési, Mihály Takács, Erzsébet Ösz, Zoltán Pintér, József Vámos, K. Takács-Novák

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Some cyclic chalcone analogues [E-2-(X-benzylidene)-1-indanones, -tetralones, and -benzosuberones], on-plate UV light-catalyzed formation of new chromatographic spots, can be observed during thin-layer chromatography (TLC). Gas chromatographic (GC) analysis of selected derivatives indicates the formation of one new substance in each case. GC coupled with mass spectrometry and 1H NMR analysis of the samples reveals that the compounds formed are the respective Z-2-(X-benzylidene)-1-indanones, -tetralones, and -benzosuberones. Two-dimensional TLC shows that the E/Z isomerization is a reversible process. By means of the RP-TLC, the logarithm of n-octanol-water partition coefficient (log P) values of F- and Z-isomeric pairs of selected 2-(X-benzylidene)-1-benzosuberones is determined. The Z-isomers are less lipophilic than the E-isomers.

Original languageEnglish
Pages (from-to)289-295
Number of pages7
JournalJournal of Chromatographic Science
Volume43
Issue number6
Publication statusPublished - Jul 2005

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Chalcone
Thin layer chromatography
Indans
Thin Layer Chromatography
Tetralones
Isomerization
Light
Isomers
1-Octanol
Ultraviolet Rays
Ultraviolet radiation
Gas chromatography
Gas Chromatography
Mass spectrometry
Mass Spectrometry
Gases
Nuclear magnetic resonance
Derivatives
Water
benzosuberone

ASJC Scopus subject areas

  • Analytical Chemistry
  • Clinical Biochemistry

Cite this

In-solution and on-plate light-catalyzed E/Z isomerization of cyclic chalcone analogues. Lipophilicity of F- and Z-2-(X-benzylidene)-1-benzosuberones. / Perjési, P.; Takács, Mihály; Ösz, Erzsébet; Pintér, Zoltán; Vámos, József; Takács-Novák, K.

In: Journal of Chromatographic Science, Vol. 43, No. 6, 07.2005, p. 289-295.

Research output: Contribution to journalArticle

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AU - Vámos, József

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