Fluorinated chalcones are organic compounds with diverse biological activities and are of interest for drug development due to their improved properties, such as lipophilicity, bioavailability, and metabolic stability. Therefore, the correlation between structure and properties is fundamental to discover the potential use on pharmaceutical and technological applications. In this sense, we synthesized and characterized a novel fluorinated chalcone (E)-1-(4-fluorophenyl)-3-(naphthalen-1-yl)prop-2-en-1-one (FCH), and compared its supramolecular arrangement and topological analysis with a chalcone (E)-1-(4-hydroxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one (HCH). The molecular electrostatic potential, QTAIM, and frontier molecular orbitals of both chalcones were investigated using the M06-2X/6-311++G(d,p) level of theory. Our findings show that the FCH exhibits a herringbone packing with intermolecular interactions of C–H⋯F and C–H⋯π, while the HCH assumes a staircase packing coordinated by O–H⋯O and π⋯π intermolecular interactions. Furthermore, the electrostatic potential analysis shows that FCH is susceptible to electrophilic attack, while HCH is susceptible to nucleophilic attack. Finally, the structural basis analysis for both chalcones indicated that FCH has a higher lipophilicity than HCH due to the stronger hydrogen bond of HCH with water.

中文翻译：

---

新型萘-查耳酮类似物氟取代的结构基础

氟化查耳酮是具有多种生物活性的有机化合物，由于其改进的特性（例如亲脂性、生物利用度和代谢稳定性）而受到药物开发的关注。因此，结构和性质之间的相关性对于发现药物和技术应用的潜在用途至关重要。在此意义上，我们合成并表征了一种新型氟化查尔酮 (E)-1-(4-氟苯基)-3-(萘-1-基)丙-2-烯-1-酮 (FCH)，并比较了其超分子用查耳酮 (E)-1-(4-羟基苯基)-3-(naphthalen-1-yl)prop-2-en-1-one (HCH) 进行排列和拓扑分析。使用 M06-2X/6-311++G(d,p) 理论水平研究了两种查尔酮的分子静电势、QTAIM 和前沿分子轨道。我们的研究结果表明，FCH 表现出人字形堆积，具有 C–H⋯F 和 C–H⋯π 的分子间相互作用，而 HCH 则呈现由 O–H⋯O 和 π⋯π 分子间相互作用协调的阶梯堆积。此外，静电势分析表明，FCH易受亲电攻击，而HCH易受亲核攻击。最后，两种查尔酮的结构基础分析表明，由于 HCH 与水的氢键更强，FCH 的亲脂性高于 HCH。而 HCH 易受亲核攻击。最后，两种查尔酮的结构基础分析表明，由于 HCH 与水的氢键更强，FCH 的亲脂性高于 HCH。而 HCH 易受亲核攻击。最后，两种查尔酮的结构基础分析表明，由于 HCH 与水的氢键更强，FCH 的亲脂性高于 HCH。