Hamzehloueian Mahshid, Davari Zakieh
Department of Chemistry, Jouybar Branch, Islamic Azad University, Jouybar, Iran.
Department of Chemistry, Jouybar Branch, Islamic Azad University, Jouybar, Iran.
J Mol Graph Model. 2018 Mar;80:32-37. doi: 10.1016/j.jmgm.2017.12.019. Epub 2017 Dec 29.
The molecular mechanism of the [3+2] cycloaddition (32CA) reaction of an azomethine ylide, generated in situ from isatin and sarcosine, with benzo-imidazol-2-yl-3-phenylacrylonitrile have been theoretically studied by using DFT at the B3LYP and M06-2X levels of theory. This reaction takes place through an asynchronous one-step mechanism. Analysis of the global electron density transfer (GEDT) indicates that this 32CA has a polar character. The regiochemistry of this reaction was investigated using Parr functions analysis, as well as HSAB principle and potential energy surface analysis, where the results are in agreement with the experimental observations. The ELF analysis revealed that this 32CA reaction takes place through a two-stage one-step mechanism.
通过密度泛函理论（DFT）在B3LYP和M06 - 2X理论水平上，对由异吲哚酮和肌氨酸原位生成的甲亚胺叶立德与苯并咪唑 - 2 - 基 - 3 - 苯基丙烯腈的[3 + 2]环加成（32CA）反应的分子机制进行了理论研究。该反应通过非同步一步机制进行。全局电子密度转移（GEDT）分析表明，此32CA具有极性特征。使用帕尔函数分析、软硬酸碱（HSAB）原理以及势能面分析对该反应的区域化学进行了研究，结果与实验观察结果一致。分子中的电子定域函数（ELF）分析表明，此32CA反应通过两阶段一步机制进行。
