Teorijsko, spektroskopsko i hromatografsko proučavanje strukture i svojstava para- supstituisanih derivata 5-benzilidenbarbiturne kiseline sa elektron-donorskimm i elektron-akceptorskim supstituentima
Theoretical, spectroscopic, and chromatographic study of the structure and properties of para-substituted 5-benzylidenebarbituric acid derivatives with electron-donor and electron-acceptor substituents
Committee membersRančić, Milica
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Faculty:Универзитет у Београду, Хемијски факултет
Keywords:Derivati barbiturne kiseline, push-pull sistemi, LFER analiza, ICT proces, "hole-electron" analiza, lipofilnost, RP TLC, logP, multivarijantna analiza / 5-Benzylidenebarbiturates show different biological activities that are significantly influenced by the physical, chemical, and structural properties of the compound, as well as interesting optical properties resulting from donor-acceptor interaction in the molecules. A series of para-substituted 5-benzylidenebarbituric acid derivatives as potential push-pull electronic systems with electron-donor and electron-acceptor substituents was synthesized. The potential electron-donor abilities of barbituric acid, which are still not established in the literature, and donor-acceptor interactions in the synthesized compounds were investigated. The electronic interactions in the ground state were investigated by LFER analysis on 13C NMR data together with the analysis of optimized geometries and calculated electron densities. The electron excitations and the nature of excited state were studied by LSER analysis and TDDFT calculations. The results of the “hole-electron” analysis and calculated ICT descriptors during the excitation show that the p-N(CH3)2 derivative is the best candidate for the push-pull system. It has been found that barbituric acid can be a weak electron-donor when coupled with a strong electron-acceptor. The chromatographic lipophilicity parameters of the synthesized compounds were determined by the RP TLC in methanol, n-propanol, acetone, and tetrahydrofuran. The relationship between chromatographic lipophilicity parameters (RМ0 and m), theoretically calculated logP values as a standard measure of lipophilicity, pharmacokinetic and toxicological parameters was examined using the linear regression, cluster analysis, and principal component analysis. The retention behavior of the investigated compounds is significantly conditioned by the nature of the substituents as well as their electronic effects. The results confirm that the chromatographic parameters (RМ0 and m) can be used to describe the lipophilicity of the investigated compounds.
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