Cyclization of 4-Hydroxy-4-methyl-1-pentyl<i>p</i>-Toluenesulfonate as a Model to Evaluate Inherent Medium Effect on S<sub>N</sub>2 Solvolysis
作者:Nobujiro Shimizu、Toru Tsutsumi、Yuho Tsuno
DOI:10.1246/cl.1991.2065
日期:1991.11
Solvent effect on the cyclization of 4-hydroxy-4-methyl-1-pentyl p-toluenesulfonate, a mechanistic equivalent to the SN2 solvolysis, was successfully analyzed by the Taft LSER equation as log k = 3.2π* + 1.4α + 1.9β − 8.36, indicating that three independent factors are operative, i.e., solvent polarity and H-bond donor ability which promote ionization, and H-bond acceptor ability which enhances nucleophilicity
通过 Taft LSER 方程成功分析了溶剂对 4-羟基-4-甲基-1-戊基对甲苯磺酸酯环化的影响,其机理等同于 SN2 溶剂分解,log k = 3.2π* + 1.4α + 1.9β - 8.36,表明三个独立因素起作用,即促进电离的溶剂极性和H键供体能力,以及增强内部OH基团的亲核性的H键受体能力。