Browsing by Author "M. Serdar ÇAVUŞ"

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Analysis of Relationship Between Some Disazo Dyes Derived from 2,4- Dihydroxyquinoline and Its Anticancer and DNA Binding Properties by Density Functional Theory
(2021-05-01) M. Serdar ÇAVUŞ; Nesrin ŞENER
It was studied some physical and chemical properties of 2,4-dihydroxy quinoline derivative diazo dyes by theoretical methods. Six different solvents were used to determine the solvatochromic behavior and absorption of the compounds, and the experimental results were compared with the theoretical data obtained from quantum chemical calculations. DFT calculations were carried out to obtain the geometric, electronic and some chemical reactivity parameters of the compounds. The atom in molecule, natural bond orbital, density of state, noncovalent interaction, Fukui function, electron localization function, and electron delocalization range analyzes of the compounds were performed to determine the relationship between the electronic properties and the DNA binding capacity and the cytotoxicity against HeLa and PC3 cancer cell lines. It was observed that the compounds substituted with –Cl and –NO2 had higher DNA binding and higher anticancer effect. Besides the positions of the substituents, the electron density in the bonds, the delocalization index values and the distribution of the nucleophilic and electrophilic attack sites are among the important factors determining the reactivity of the compounds. In addition, the HOMO energies of the compounds with better DNA binding properties were calculated higher than the other compounds.
Synthesis and Analysis of Some Azo Dyes Obtained from Benzothiazole by Density Functional Theory
(2023-06-22) Nesrin ŞENER; M. Serdar ÇAVUŞ
In this study, two different azo dyes were synthesized from the reaction of 2-amino benzothiazole derivative amine and heterocyclic coupling compounds. The structures of the synthesized compounds were characterized such as by 1H-NMR and FT-IR spectroscopic methods. Four different possible tautomer structures are contemplated for each of the compounds. Considering the spectroscopic results analysis, the molecular structure of each tautomer was evaluated. UV-Vis. absorption properties of the obtained azo dyestuff compounds were studied using six different solvents. On the other hand, the electronic data of the spectroscopic and absorption properties of the tautomeric structures of the final products were examined theoretically at the B3LYP/6-311++G(2d,2p) theory level with the DFT approach. The experimental and theoretical results obtained in the study were compared with each other and the results were discussed.
Synthesis, Structural Characterization And Theoretical Investigations of New Azo-Azomethine Compounds Bearing Acryloyl Moiety
(2018-06-01) M. Serdar ÇAVUŞ; Sevil ÖZKINALI; Büşra SAKİN
In this study six new azo-azomethine dyes containing acryloyl group, 4-[[[4-[4′-methylphenyl azo) phenyl] imino] methyl] phenyl-2-propenoat, 4-[[[4-[4′- hydroxy phenylazo)phenyl] imino] methyl] phenyl-2-propenoat, 4-[[[4-(phenyl azo) phenyl] imino]methyl]- phenyl-2-propenoat, 4-[[[4-[4′-chloro phenyl azo) phenyl] imino] methyl]phenyl-2-propenoat, 4-[[[4-[4′- nitro phenyl azo) phenyl] imino] methyl] phenyl-2-propenoat were synthesized. The acryloyl derivatives of the azo-azomethine dyes wereprepared with metallic sodium and acryloyl chloride in 1:1 Molar ratio and characterizedusing elemental analysis, IR, UV-Vis, 1H-NMR and 13C-NMR spectroscopy. Themolecular geometry was also optimized using density functional theory (DFT/B3LYP)method with the 6-311G(2d,2p) and cc-pvtz basis sets in ground state. From theoptimized geometry of the compounds, vibrational frequencies, UV-Vis, molecularelectrostatic potential distribution and frontier molecular orbitals were performed usingsame method and basis stets, and the results were compared with the experimental data.