An Experimental and Computational Exploration on the Electronic, Spectroscopic, and Reactivity Properties of Novel Halo-Functionalized Hydrazones

[Image: see text] 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, (1)H-NMR, (13)C-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.