应用量子化学反应性指数研究频哪醇重排反应

Study on the Rearrangement of Pinacol by Quantum Chemical Reactivity Index

1,2-二醇类化合物的频哪醇重排反应是经典的化学重排反应。无环的或环状的1,2-二醇类化合物在质子酸或路易斯酸的作用下会重排发生取代基的1,2-迁移,其产物往往伴随不同基团的迁移而生。但是,主产物取决于二羟基相连接的碳原子上取代基的空间架构和性质。本文采用净亲电指数(Multiphilic index)和Wiberg键级等量子化学反应性指数来定量描述1,2-二醇类化合物的频哪醇重排反应机理,并依此作为预测频哪醇反应主产物的依据。

Pinacol rearrangement of 1,2-diols is a classical chemical rearrangement.Including acyclic and cyclic 1,2-diols,under the action of protonic acid or Lewis acid,the 1,2-transfer of substituents occurs,and the products are often generated with the migration of different groups.However,the main product depends on the spatial structure and properties of the substituents on the dihydroxy linked carbon atoms.In this paper,the mechanism of pinacol rearrangement of 1,2-diols is quantitatively described by using the net electrophilic index(Multiphilic index),Wiberg bond index and other quantum chemical reactivity indexes,which can be used as the basis for predicting the main products of pinacol rearrangement.