苯乙烯与苯酚反应的前线轨道理论分析

Frontier molecular orbital analysis on the reaction between styrene and phenol

采用密度泛函理论的M062X方法和6-311G(d,p)基组,对苯乙烯与苯酚的反应进行了分子轨道理论计算.通过讨论反应过程中各分子的最高占据轨道(HOMO)和最低空轨道(LUMO),预测了化学反应的方向和相应的反应产物.经过前线轨道理论分析,得出苯乙烯与苯酚反应的关键步骤是形成苯乙烯基碳正离子,反应中H+起到催化作用;反应产物主要有4-(1-苯基乙基)苯酚、2-(1-苯基乙基)苯酚、2,4-双-(1-苯基乙基)苯酚、2,4,6-三-(1-苯基乙基)苯酚(SP-3)、1,3-二苯基丁烯和4-(1,2-二苯丙基)苯酚.

Utilizing the B3LYP method M062X at the level of 6-311G（d,p） basis set, the chemical reaction between styrene and phenol was simulated based on the molecular orbital theory. According to analysis of the calculation results of the attributes of the highest occupied orbital （HOMO） and the lowest unoccupied molecular orbital （LUMO）, the direction of chemical reaction and the chemical products were figured out. Based on the analysis of the frontier molecular orbital theory （FMO）, one can draw a conclusion that the formation of styrene carbonations is the critical process in the reaction system, and the hydrogen ion plays an import role as the catalyst of the reactions. The reaction products mainly include 4-（1-phenylethyl）phenol, 2-（1-phenylethyl）phenol, 2,4-bis（1-phenylethyl）phenol, 2,4,6-tris（1-phenylethyl）-phenol, but-1-ene-1,3-diyldibenzene and 4-（1,2-diphenylpropyl）phenol.