Synthesis, Structural Characterization and Theoretical Investigations of New Azo-Azomethine Compounds Bearing Acryloyl Moiety
In this study six new azo-azomethine dyes containing acryloyl group, 4-[[[4-[4-methylphenylazo)phenyl]imino]methyl]phenyl-2-propenoat, 4-[[[4-[4-hydroxyphenyl-azo)phenyl]imino]methyl]phenyl-2-propenoat, 4-[[[4-(phenylazo)phenyl]imino]methyl]-phenyl-2-propenoat, 4-[[[4-[4-chlorophenylazo)phenyl]imino]methyl]phenyl-2-propenoat, 4-[[[4-[4-nitrophenylazo)phenyl]imino]methyl]phenyl-2-propenoat were synthesized. The acryloyl derivatives of the azo-azomethine dyes were prepared with metallic sodium and acryloyl chloride in 1:1 Molar ratio and characterized using elemental analysis, IR, UV-Vis, 1H-NMR and 13C-NMR spectroscopy. The molecular 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 the optimized geometry of the compounds, vibrational frequencies, UV-Vis, molecular electrostatic potential distribution and frontier molecular orbitals were performed using same method and basis stets, and the results were compared with the experimental data.
Azo-Azomethine; Schiff bases; Imine group; DFT; Acryloyl chloride
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