Chemistry Department, Faculty of Education, Ain Shams University, Roxy, Cairo, 11711, Egypt.
Chemistry Department, Faculty of Science, Suez University, Suez, 43518, Egypt.
Sci Rep. 2023 Jun 1;13(1):8909. doi: 10.1038/s41598-023-35933-8.
The tautomerizations mechanism of 4-(methylsulfanyl)-3[(1Z)-1-(2-phenylhydrazinylidene) ethyl] quinoline-2(1H)-one were inspected in the gas phase and ethanol using density function theory (DFT) M06-2X and B3LYP methods. Thermo-kinetic features of different conversion processes were estimated in temperature range 273-333 K using the Transition state theory (TST) accompanied with one dimensional Eckert tunneling correction (1D-Eck). Acidity and basicity were computed as well, and the computational results were compared against the experimental ones. Additionally, NMR, global descriptors, Fukui functions, NBO charges, and electrostatic potential (ESP) were discussed. From thermodynamics analysis, the keto form of 4-(methylsulfanyl)-3-[(1Z)-1-(2 phenylhydrazinylidene) quinoline-2(1H)-one is the most stable form in the gas phase and ethanol and the barrier heights required for tautomerization process were found to be high in the gas phase and ethanol ~ 38.80 and 37.35 kcal/mol, respectively. DFT methods were used for UV-Vis electronic spectra simulation and the time-dependent density functional theory solvation model (TDDFT-SMD) in acetonitrile compounds.
4-(甲硫基)-3-[(1Z)-1-(2-苯腙基)乙基]喹啉-2(1H)-酮的互变异构机制在气相和乙醇中使用密度泛函理论（DFT）M06-2X 和 B3LYP 方法进行了检查。使用过渡态理论（TST）和一维埃克特隧道修正（1D-Eck），在 273-333 K 的温度范围内估算了不同转化过程的热动力学特征。还计算了酸度和碱度，并将计算结果与实验结果进行了比较。此外，讨论了 NMR、全局描述符、福井函数、NBO 电荷和静电势（ESP）。从热力学分析可以看出，4-(甲硫基)-3-[(1Z)-1-(2-苯腙基)喹啉-2(1H)-酮的酮式在气相和乙醇中是最稳定的形式，并且互变异构过程所需的势垒高度在气相和乙醇中分别为 38.80 和 37.35 kcal/mol。DFT 方法用于模拟 UV-Vis 电子光谱和在乙腈化合物中的含时密度泛函理论溶剂化模型（TDDFT-SMD）。
