Structural Dynamics of 5-Phenyl-1H-Pyrazol-3-ol Compound

IF 0.7 4区化学 Q4 CRYSTALLOGRAPHY

Journal of Chemical Crystallography Pub Date : 2026-04-06 DOI:10.1007/s10870-026-01092-7

Ersin Acar, Issam Ameziane El Hassani, Emine Berrin Poyraz, Suhana Arshad, M’hammed Ansar, Necmi Dege, Khalid Karrouchi

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引用次数: 0

Abstract

In this study, the compound 5-phenyl-1H-pyrazole-3-ol (\({C}_{9}{H}_{8}{N}_{2}\) O) was structurally investigated. The compound was characterized through both experimental and theoretical approaches, including 1H NMR, 13C NMR, ESI-HRMS, single crystal X-ray diffraction (SCXRD), density functional theory (DFT), Hirshfeld surface analysis (HSA), and molecular docking (MD). The molecule, composed of C, H, N, and O atoms, is non-planar. In the crystal structure, intermolecular interactions are observed as O−H···N and N−H···O hydrogen bonds. Using the DFT/B3LYP-LanL2DZ level of theory, molecular electrostatic potential (MEP) and frontier molecular orbitals (Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO)) were analyzed, and properties such as chemical reactivity, electronegativity, softness and hardness were reported. In addition to these molecular properties, frontier orbital energy calculations were also performed. HSA was used to observe the contributions of various intermolecular interactions within the compound. HSA showed that the major contributions originated from H···H (41.8%), C···H (26.3%) and N···H (13.2%) interactions. MD studies against GSK-3β (PDB ID: 1Q3W) show a binding energy of −6.57 kcal/mol and an estimated inhibition constant (Ki) of 15.34 µM with a ligand efficiency of −0.55.

Graphical Abstract

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5-苯基- 1h -吡唑-3-醇化合物的结构动力学

本研究对化合物5-苯基- 1h -吡唑-3-醇（\({C}_{9}{H}_{8}{N}_{2}\) O）进行了结构研究。通过1H NMR、13C NMR、ESI-HRMS、单晶x射线衍射（SCXRD）、密度泛函理论（DFT）、Hirshfeld表面分析（HSA）、分子对接（MD）等实验和理论方法对化合物进行了表征。这种分子由碳、氢、氮和氧原子组成，是非平面的。在晶体结构中，分子间相互作用表现为O−H··N和N−H··O氢键。利用理论的DFT/B3LYP-LanL2DZ能级，分析了分子静电势（MEP）和前沿分子轨道（最高已占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）），并报告了其化学反应性、电负性、软性和硬度等性质。除了这些分子性质外，还进行了前沿轨道能量的计算。用HSA观察了化合物内各种分子间相互作用的贡献。HSA结果表明，H···H（41.8）是主要贡献源%), C···H (26.3%) and N···H (13.2%) interactions. MD studies against GSK-3β (PDB ID: 1Q3W) show a binding energy of −6.57 kcal/mol and an estimated inhibition constant (Ki) of 15.34 µM with a ligand efficiency of −0.55.Graphical Abstract

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来源期刊

Journal of Chemical Crystallography 化学-光谱学

CiteScore

1.50

自引率

12.50%

发文量

审稿时长

6.3 months

期刊介绍： Journal of Chemical Crystallography is an international and interdisciplinary publication dedicated to the rapid dissemination of research results in the general areas of crystallography and spectroscopy. Timely research reports detail topics in crystal chemistry and physics and their relation to problems of molecular structure; structural studies of solids, liquids, gases, and solutions involving spectroscopic, spectrometric, X-ray, and electron and neutron diffraction; and theoretical studies.