DFT Study of Benzofuroxan Synthesis Mechanism from 2-Nitroaniline via Sodium Hypochlorite  

2-硝基苯胺合成苯并氧化呋咱反应的密度泛函研究

作　　者：侯春园[1] 陈晓芳[1] 刘建勇[1] 来蔚鹏 王伯周 

机构地区：[1]中国科学院大连化学物理研究所分子反应动力学国家重点实验室,大连116023 [2]西安现代化学研究所,西安710065

出　　处：《Chinese Journal of Chemical Physics》2010年第4期387-392,I0001,共7页化学物理学报（英文）

摘　　要：The oxidative cyclization reaction of 2-nitroaniline via sodium hypochlorite to yield benzo- furoxan is investigated by the hybrid density functional theory B3LYP/6-31G（d,p） method. Solvent effects are estimated with the polarizable continuum model to optimize structures. The title reaction is predicted to undergo two pathways, each of which is a stepwise process. Path A includes four steps, namely oxidization, H-attack, hydrolysis, and cyclization. Path B involves the nucleophilic attack of OH^- to the H atom of the N-H bond and the proton transfer to the N atom of amino group leading to the cleavage of the N-H single bond in the amino group. The calculated results indicate that path A is favored mechanism for the title reaction. Furthermore, it is rational for one water molecule serving as a bridge to assist in the hydrolysis step of Path A and our calculations exhibit that this process is the rate-determining step.

关 键 词：BENZOFUROXAN Density functional theory 2-Nitroaniline 

分 类 号：O[理学]