Hydrazones derivatives from halo-pyridinol: Synthesis and DFT-based theoretical exploration

IF 1.2 4区综合性期刊 Q3 MULTIDISCIPLINARY SCIENCES

Kuwait Journal of Science Pub Date : 2025-01-16 DOI:10.1016/j.kjs.2025.100375

Mohammed A. Assiri , Muhammad Suleman , Muhammad Ibrahim , Tanveer Hussain Bokhari , Ajaz Hussain , Aijaz Rasool Chaudhry , Iqra Mehwish , Rabia Nawaz , Perveen Kanwal , Faiz Rasool

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引用次数: 0

Abstract

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.

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卤代吡啶醇腙衍生物的合成及基于dft的理论探索

成功合成了三个新型的卤吡啶基腙衍生物，它们具有虚拟光电性质。它们是(E)-2-（（2-氯吡啶-3-基）氧）- n '-（4-氟苄啶）乙酰肼（CPFH）， (E)- n '-（4-氯苄啶）-2-（（2-氯吡啶-3-基）氧）乙酰肼（CCPH）和(E)-2-（（2-氯吡啶-3-基）氧）- n '-（4-甲基苄啶）乙酰肼（CPMH）。所有这些化合物都已通过核磁共振和红外光谱技术进行了广泛的表征。此外，利用ꞷB97XD/ 6-31 +g（d,p）方法进行量子化学计算，研究了它们的光电行为。利用密度泛函理论（DFT）计算了合成化合物的各种性质，包括NBO（自然键轨道）、NLO（非线性光学性质）、NPA（自然居群分析）和FMO（前沿分子轨道）分析。此外，在ꞷB97xd/ 6-31 +g（d,p）水平上，使用时间依赖DFT （TD-DFT）方法研究了这些化合物的光物理性质。DFT研究表明，化合物CPMH比CCPH和CPFH具有更高的稳定能。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Kuwait Journal of Science MULTIDISCIPLINARY SCIENCES-

CiteScore

1.60

自引率

28.60%

发文量

132

期刊介绍： Kuwait Journal of Science (KJS) is indexed and abstracted by major publishing houses such as Chemical Abstract, Science Citation Index, Current contents, Mathematics Abstract, Micribiological Abstracts etc. KJS publishes peer-review articles in various fields of Science including Mathematics, Computer Science, Physics, Statistics, Biology, Chemistry and Earth & Environmental Sciences. In addition, it also aims to bring the results of scientific research carried out under a variety of intellectual traditions and organizations to the attention of specialized scholarly readership. As such, the publisher expects the submission of original manuscripts which contain analysis and solutions about important theoretical, empirical and normative issues.