Crystalline organic compounds, (E)-N-(2-(2-(2-hydroxybenzylidene)hydrazinecarbonyl)-phenyl) benzamide (NHBPB) and (E)-4-chloro-N-(2-(2-(2-hydroxybenzylidene)hydrazine-carbonyl) phenyl)benzene sulfonamide (CNHBP), were prepared through condensation of hydrazide derivatives of N-benzoylated and N-4-chlorobenzenesulfonylated derivatives of anthranilic acid with 2-hydroxybenzaldehyde. The structural interpretations were accomplished distinctly by single-crystal X-ray diffraction (SC-XRD) analysis and NMR studies. Accompanying the experimental studies, quantum chemical computations were employed to determine the non-linear optical (NLO) properties using the M06 and M06-2X functionals along with 6-311G (d,p) basis set. A comparative analysis was made in order to compare the geometrical parameters between XRD and DFT calculations and a good agreement was found. Frontier molecular orbital (FMO) analysis found a narrower HOMO/LUMO energy gap for NHBPB than CNHBP. Further, UV-Vis investigation revealed a red-shifted behavior for NHBPB (297.894 and 311.594 nm at M06-2X and M06 levels, respectively) owing to its smaller HOMO/LUMO energy gap. From the FMOs findings, Global Reactivity Parameters (GRPs) were also calculated and a relatively lower ionization potential and hardness with larger softness were found for NHBPB. The FMO and UV results indicated the greater polarizability in NHBPB as compared to CNHBP. Therefore, greater second hyperpolarizability response was noticed for NHBPB (2.749 ×10⁵ and 1.945×10⁵ a.u at M06-2X and M006 functional, respectively). Additionally, comparative study with urea molecule showed good NLO responses for the foresaid compounds. These findings revealed that hydrazide-based compounds possess extremely high linear and nonlinear polarizabilities compared to most of the previously synthesized compounds which highlights their excellent properties for use in NLO materials.

结晶有机化合物，( E ) -N- (2-(2-(2-羟基亚苄基)肼羰基)-苯基)苯甲酰胺( NHPBB )和( E )-4-氯-N- (2-(2-(2-)羟基亚苄基）肼-羰基）苯基）苯磺酰胺（CNHBP）是由N-苯甲酰化的酰肼衍生物与N邻氨基苯甲酸与 2-羟基苯甲醛的 -4-氯苯磺酰化衍生物。通过单晶 X 射线衍射 (SC-XRD) 分析和 NMR 研究清楚地完成了结构解释。伴随实验研究，使用 M06 和 M06-2X 泛函以及 6-311G (d,p) 基组，采用量子化学计算来确定非线性光学 (NLO) 特性。为了比较XRD和DFT计算之间的几何参数，进行了比较分析，发现了良好的一致性。前沿分子轨道 (FMO) 分析发现 NHBPB 的 HOMO/LUMO 能隙比CNHBP窄。此外，UV-Vis 研究揭示了NHBPB的红移行为（297.894 和 311.594纳米在 M06-2X 和 M06 水平，分别）由于其较小的 HOMO/LUMO 能隙。根据 FMO 的发现，还计算了全局反应参数 (GRP)，发现NHBPB的电离势和硬度相对较低，而柔软度较大。FMO 和 UV 结果表明，与CNHBP相比，NHPBB的极化率更高。因此，NHPBB（2.749 ×10 ⁵和 1.945×10 ⁵ a.u在 M06-2X 和 M006 功能，分别）。此外，与尿素分子的比较研究表明，上述化合物具有良好的 NLO 响应。这些发现表明，与大多数先前合成的化合物相比，基于酰肼的化合物具有极高的线性和非线性极化率，这突出了它们在 NLO 材料中的优异性能。