Hydrazones derivatives from halo-pyridinol: Synthesis and DFT-based theoretical exploration
Three novel halo-pyridinol-based hydrazone derivatives were synthesized successfully for their virtual optoelectronic properties. These are (E)-2-((2-chloropyridin-3-yl)oxy)-N'-(4-fluorobenzylidene)acetohydrazide (CPFH), (E)-N'-(4-chlorobenzylidene)-2-((2-chloropyridin-3-yl)oxy)acetohydraz...
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| Format: | Article |
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| Language: | English |
| Published: |
Elsevier
2025-04-01
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| Series: | Kuwait Journal of Science |
| Subjects: | |
| Online Access: | https://www.sciencedirect.com/science/article/pii/S2307410825000197 |
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| Summary: | Three novel halo-pyridinol-based hydrazone derivatives were synthesized successfully for their virtual optoelectronic properties. These are (E)-2-((2-chloropyridin-3-yl)oxy)-N'-(4-fluorobenzylidene)acetohydrazide (CPFH), (E)-N'-(4-chlorobenzylidene)-2-((2-chloropyridin-3-yl)oxy)acetohydrazide (CCPH), and (E)-2-((2-chloropyridin-3-yl)oxy)-N'-(4-methylbenzylidene)acetohydrazide (CPMH). All these compounds have been extensively characterized using nuclear magnetic resonance and infrared spectroscopic techniques. Additionally, their optoelectronic behavior was investigated using quantum chemical calculations with the ꞷB97XD/6–31+g(d,p) approach. Various properties of the synthesized compounds were explored using density functional theory (DFT) calculations, including NBO (natural bond orbital), NLO (non-linear optical properties), NPA (natural population analysis), and FMO (frontier molecular orbital) analyses. Furthermore, photophysical properties of these compounds were studied using a time-dependent DFT (TD-DFT) approach at the ꞷB97xd/6–31+g(d,p) level. The DFT investigations showed that compound CPMH possesses higher stabilization energy than CCPH and CPFH. © 2025 The Authors |
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| ISSN: | 2307-4108 2307-4116 |