(R)-(6-甲氧基喹啉-4-基)[(1S,2S,4S,5R)-5-乙烯基奎宁环素-2-基]甲醇四苯基硼酸盐离子对配合物的合成：表征、抗菌和计算研究,Molecules

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(R)-(6-甲氧基喹啉-4-基)[(1S,2S,4S,5R)-5-乙烯基奎宁环素-2-基]甲醇四苯基硼酸盐离子对配合物的合成：表征、抗菌和计算研究
Molecules ( IF 4.2 ) Pub Date : 2023-10-08 , DOI: 10.3390/molecules28196974
Tarek A Yousef ₁ , Haitham Alrabiah ₂ , Mohamed H Al-Agamy ₃ , Rashad Al-Salahi ₂ , Essam A Ali ₂ , Gamal A E Mostafa ₂

Affiliation

通过四苯硼酸钠与奎宁反应合成(R)-(6-甲氧基喹啉-4-基)[(1S,2S,4S,5R)-5-乙烯基奎宁环素-2-基]甲醇(奎宁)-四苯硼酸盐配合物。室温下通过离子对反应（绿色化学）生成去离子水。通过多种物理化学方法对固体复合物进行了表征。生物活性分子和/或有机分子之间离子对复合物的形成对于理解生物活性分子和受体相互作用之间的关系至关重要。检查所研究的复合物的抗菌活性。所有理论计算均使用 B3LYP 6-311G(d,p) 水平理论在真空和水中进行。理论计算可以预测和可视化离子相互作用，这解释了复合物的稳定性。能量优化结果表明Q-TPB配合物稳定且具有负络合能。获得的几何结构表明四苯硼酸和奎宁两个分子的哌啶中的硼（B−）和氮（N+）彼此接近，这使得离子相互作用成为可能。HOMO 和 LUMO 之间的适度能隙表明该化合物是稳定的。通过密度泛函理论 (TD-DFT) 在理论水平 B3LYP/6–311G(d,p) 的溶剂中计算两个模型的电子跃迁，允许检测两个模型的三个紫外/可见吸收带以及发现主人和客人之间的电荷转移。紫外吸收、红外和核磁共振氢谱与实验部分相当。

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Synthesis of (R)-(6-Methoxyquinolin-4-yl)[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methanol Tetraphenylborate Ion-Pair Complex: Characterization, Antimicrobial, and Computational Study

The (R)-(6-Methoxyquinolin-4-yl)[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methanol (quinine)-tetraphenylborate complex was synthesized by reacting sodium tetraphenyl borate with quinine in deionized water at room temperature through an ion-pair reaction (green chemistry) at room temperature. The solid complex was characterized by several physicochemical methods. The formation of ion-pair complex between bio-active molecules and/or organic molecules is crucial to comprehending the relationships between bioactive molecules and receptor interactions. The complex under study was examined for antimicrobial activity. All theoretical calculations were carried out in vacuum and water using the B3LYP level 6–311G(d,p) levels of theory. The theoretical computation allowed for the prediction and visualization of ionic interactions, which explained the complex’s stability. The results of energy optimization showed that the Q-TPB complex is stable with a negative complexation energy. The obtained geometries showed that the boron (B−) and nitrogen (N+) in piperidine of the two molecules tetraphenylborate and quinine are close to each other, which makes it possible for ions to interact. The modest energy gap between HOMO and LUMO showed that the compound was stable. The computation of the electron transitions of the two models by density functional theory (TD-DFT) in the solvent at the theoretical level B3LYP/6–311G(d,p) allowed for the detection of three UV/visible absorption bands for both models and the discovery of a charge transfer between the host and the guest. The UV absorption, infrared, and H NMR are comparable with the experimental part.

更新日期：2023-10-09

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