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
📌 3 Key Takeaways
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Objective & Hypothesis:I n this study six new azo-azomethine dyes containing acryloyl group, 4-[[[4-[4′-methyl phenyl 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-2propenoat were synthesized.
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Key Findings & Data: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.
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Conclusion & Impact: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
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Azo-Azomethine · Schiff bases · Imine group
Abstract
I n this study six new azo-azomethine dyes containing acryloyl group, 4-[[[4-[4′-methyl phenyl 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-2propenoat 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
ÖZKINALI, S., SAKİN, B., ÇAVUŞ, M. S. (2022). Synthesis, Structural Characterization and Theoretical Investigations of New Azo-Azomethine Compounds Bearing Acryloyl Moiety. Hittite Journal of Science and Engineering, Cilt: 5 - Sayı: 4, 259–269. https://ajindex.com/articles/538052
Georgiev A, Bubev E, Dimov D, Yancheva D, Zhivkov I, Krajčovič J, et al. Synthesis, structure, spectral properties and DFT quantum chemical calculations of 4-aminoazobenzene dyes. Effect of intramolecular hydrogen bonding on photoisomerization. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2017 Mar;175:76–91.
Shahab S, Sheikhi M, Filippovich L, Anatol’evich DE, Yahyaei H. Quantum chemical modeling of new derivatives of ( E,E )-azomethines: Synthesis, spectroscopic (FT-IR, UV/Vis, polarization) and thermophysical investigations. Journal of Molecular Structure. 2017 June;1137:335–48.
Purtas F, Sayin K, Ceyhan G, Kose M, Kurtoglu M. New fluorescent azo-Schiff base Cu(II) and Zn(II) metal chelates; spectral, structural, electrochemical, photoluminescence and computational studies. Journal of Molecular Structure. 2017 June;1137:461–75.
Mondal AS, Pramanik AK, Patra L, Manna CK, Mondal TK. Synthesis and characterization of a new zinc(II) complex with tetradentate azo-thioether ligand: X-ray structure, DNA binding study and DFT calculation. Journal of Molecular Structure. 2017 Oct;1146:146–52.
Rocha M, Di Santo A, Echeverría GA, Piro OE, Cukiernik FD, Ulic SE, et al. Supramolecular self-assembly of a new multi- conformational Schiff base through hydrogen bonds: Crystal structure, spectroscopic and theoretical investigation. Journal of Molecular Structure. 2017 Apr;1133:24–36.
Qian H-F, Tao T, Feng Y-N, Wang Y-G, Huang W. Crystal structures, solvatochromisms and DFT computations of three disperse azo dyes having the same azobenzene skeleton. Journal of Molecular Structure. 2016 Nov;1123:305–10.
Sheikhi M, Shahab S, Filippovich L, Yahyaei H, Dikusar E, Khaleghian M. New derivatives of (E,E)-azomethines: Design, quantum chemical modeling, spectroscopic (FT- IR, UV/Vis, polarization) studies, synthesis and their applications: Experimental and theoretical investigations. Journal of Molecular Structure. 2018 Jan;1152:368–85.
P. Hohenberg, W. Kohn, Inhomogeneous electron gas, Phys. Rev., 136 (1964), pp. B864–B871. Yang J, Shi R, Zhou P, Qiu Q, Li H. Asymmetric Schiff bases derived from diaminomaleonitrile and their metal complexes. Journal of Molecular Structure. 2016 Feb;1106:242–58.
Geng J, Xu D, Chang F-F, Tao T, Huang W. From heterocyclic hydrazone to hydrazone-azomethine dyes: Solvent and pH induced hydrazone and azo-keto transformation for a family of pyrazolone-based heterocyclic dyes. Dyes and Pigments. 2017 Feb;137:101–10. İspir E. The sy