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An Experimental and Computational Exploration on the Electronic, Spectroscopic, and Reactivity Properties of Novel Halo-Functionalized Hydrazones
- Source :
- ACS Omega, ACS Omega, Vol 5, Iss 30, Pp 18907-18918 (2020), Repositório Institucional da USP (Biblioteca Digital da Produção Intelectual), Universidade de São Paulo (USP), instacron:USP
- Publication Year :
- 2020
- Publisher :
- American Chemical Society, 2020.
-
Abstract
- Herein, halo-functionalized hydrazone derivatives “2-[(6′-chloroazin-2′-yl)­oxy]-N′-(2-fluorobenzylidene) aceto-hydrazone (CPFH), 2-[(6′-chloroazin-2′-yl)­oxy]-N′-(2-chlorobenzylidene) aceto-hydrazones (CCPH), 2-[(6′-chloroazin-2′-yl)­oxy]-N′-(2-bromobenzylidene) aceto-hydrazones (BCPH)” were synthesized and structurally characterized using FTIR, 1H-NMR, 13C-NMR, and UV–vis spectroscopic techniques. Computational studies using density functional theory (DFT) and time dependent DFT at CAM-B3LYP/6-311G (d,p) level of theory were performed for comparison with spectroscopic data (FT-IR, UV–vis) and for elucidation of the structural parameters, natural bond orbitals (NBOs), natural population analysis, frontier molecular orbital (FMO) analysis and nonlinear optical (NLO) properties of hydrazones derivatives (CPFH, CCPH, and BCPH). Consequently, an excellent complement between the experimental data and the DFT-based results was achieved. The NBO analysis confirmed that the presence of hyper conjugative interactions was pivotal cause for stability of the investigated compounds. The energy gaps in CPFH, CCPH, and BCPH were found as 7.278, 7.241, and 7.229 eV, respectively. Furthermore, global reactivity descriptors were calculated using the FMO energies in which global hardness revealed that CPFH was more stable and less reactive as compared to BCPH and CCPH. NLO findings disclosed that CPFH, CCPH, and BCPH have superior properties as compared to the prototype standard compound, which unveiled their potential applications for optoelectronic technology.
- Subjects :
- chemistry.chemical_classification
Materials science
General Chemical Engineering
COMPOSTOS HETEROCÍCLICOS
Hydrazone
General Chemistry
Article
Nonlinear optical
Chemistry
chemistry
Atomic orbital
Computational chemistry
Molecular orbital
Reactivity (chemistry)
Density functional theory
Fourier transform infrared spectroscopy
QD1-999
Natural bond orbital
Subjects
Details
- Language :
- English
- ISSN :
- 24701343
- Volume :
- 5
- Issue :
- 30
- Database :
- OpenAIRE
- Journal :
- ACS Omega
- Accession number :
- edsair.doi.dedup.....6660a1282b0288d6d23cb38753810cf2