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首页> 外文期刊>Computational Chemistry >Theoretical Study by Density Functional Theory Method (DFT) of Stability, Tautomerism, Reactivity and Prediction of Acidity of Quinolein-4-One Derivatives
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Theoretical Study by Density Functional Theory Method (DFT) of Stability, Tautomerism, Reactivity and Prediction of Acidity of Quinolein-4-One Derivatives

机译：密度泛函理论方法（DFT）对喹诺酮-4-一衍生物的稳定性，互变异构性，反应性和酸度预测的理论研究

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摘要

A theoretical study of the reactivity of quinoline-4-one derivatives is undertaken in order to understand the involved mechanisms. The calculations were carried out in gas phase and in N, N-Dimethylformamide (DMF) solution. The Density Functional Theory (DFT) with B3LYP functional associated to 6-311G (d) and 6-311+G (d) bases is used to perform these calculations. The results of the thermodynamic parameters showed that there is an equilibrium relation between the different tautomers. This equilibrium can be used to explain the failure to obtain tetrahydroquinoline from 5,8-dimethoxy-quinolin-4-one. Reactivity analysis from Frontier Molecular Orbitals theory and Fukui function calculations revealed that ketone forms are less reactive than enol ones. The methoxyl substituent decreases the acidity of the nitrogen and oxygen atoms of quinolin-4-one while the bromine increases the acidity of the same sites. These results foresee that nitrogen deprotonation in the case of the brominated compound is easier than in the case of methoxylated ones.
机译：为了理解所涉及的机理，对喹啉-4-一衍生物的反应性进行了理论研究。计算是在气相和N，N-二甲基甲酰胺（DMF）溶液中进行的。使用与6-311G（d）和6-311 + G（d）碱基相关联的具有B3LYP功能的密度泛函理论（DFT）来执行这些计算。热力学参数的结果表明，不同的互变异构体之间存在平衡关系。该平衡可用于解释无法从5，8-二甲氧基-喹啉-4-酮获得四氢喹啉。根据前沿分子轨道理论进行的反应性分析和Fukui函数计算表明，酮形式的反应性不如烯醇形式。甲氧基取代基降低了喹啉-4-一的氮和氧原子的酸度，而溴提高了相同位点的酸度。这些结果预见到，在溴化化合物的情况下，氮去质子化比在甲氧基化化合物的情况下更容易。

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