SN2亲核取代反应制备环氧丁烷的反应机理

SN2亲核取代反应制备环氧丁烷的反应机理 Reaction Mechanism of Substitution Nucleophilic Unimolecular（SN2） of 1,2-Epoxybutane 于海艳 YU Haiyan 1 first-author 盐城师范学院化学化工学院 盐城师范学院化学化工学院 School of Chemistry and Chemical Engineering,Yancheng Normal University School of Chemistry and Chemical Engineering,Yancheng Normal University 用密度泛函B3LYP/6-311G**理论,全自由度优化气相和水相及甲醇相中分子内SN2亲核取代反应制备环氧丁烷反应的各反应物和产物的几何构型,得其气相和水相中的几何结构和电子结构,PCM（极化连续介质模型）反应场溶剂模型用于液相计算.进一步研究不同的溶剂对SN2亲核取代的反应历程的影响,探讨不同溶剂化效应对SN2亲核取代反应历程中个物质的几何结构、能量、电荷分布以及互变异构反应活化能的影响等.结果显示:在气相甲醇相中,反应物较产物更稳定,而溶剂效应和氢键的形成对亲核取代有很大影响,对亲核取代反应起到催化的作用. The molecular structures of the mechanism of substitution nucleophilic unimolecular of 1,2-epoxybutane were full optimited by the B3 LYP method using the 6-311 + + G**basis set,in both the gaseous,aqueous phases and methyl alcohol phase,with full geometry optimization. The geometry and electronic structure of the tautomers of the substitution nucleophilic unimolecular（ SN2） of 1,2-epoxybutane were obtained,and the PCM（ polqrized continuum model） solvate theory model was employed for aqueous solution calculations,and the influences of the solvent effects on the geometry,energy,charge and activation energy were discussed. The reaction mechanism of substitution nucleophilic unimolecular（ SN2） of 1,2-epoxybutane was also studied. The calculation results indicate that the reactant is more stable than the product in both the gaseous,aqueous phases and methyl alcohol phase; the solvent effect and the formation of the hydrogen bond greatly affects the mechanism of substitution nucleophilic unimolecular of 1,2-epoxybutane. 反应机理 SN2亲核取代 环氧丁烷 密度泛函理论（DFT） reaction mechanism substitution nucleophilic unimolecular（SN2） 1,2-epoxybutane DFT（density functional theory） 10.14188/j.1671-8836.2015.05.015 O623.425 江苏省高校自然科学基金（12KJD480003）资助项目 2015-05-01 2021-03-31 5 61