In-solution and on-plate light-catalyzed E/Z isomerization of cyclic chalcone analogues. Lipophilicity of E- and Z-2-(X-benzylidene)-1-benzosuberones.
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 E- and Z-isomeric pairs of selected 2-(X-benzylidene)-1-benzosuberones is determined. The Z-isomers are less lipophilic than the E-isomers.
Perjési
Pál
P
Department of Pharmaceutical Chemistry, University of Pécs, H-7624 Pécs, Rókus str. 2, Hungary. pal.perjesi@aok.pte.hu
Takács
Mihály
M
Osz
Erzsébet
E
Pintér
Zoltán
Z
Vámos
József
J
Takács-Novák
Krisztina
K
D002384:Catalysis; D047188:Chalcones / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D008401:Gas Chromatography-Mass Spectrometry; D007536:Isomerism; D008027:Light; D008055:Lipids / Q000737:chemistry*; D012996:Solutions
D047188:Chalcones; D008055:Lipids; D012996:Solutions