Investigation of Markovnikov reactions of alkenes via ABEEM-σπ model

被引：5

作者：

Ding, Yan-Li ^{[1
]}

Yang, Zhong-Zhi ^{[2
]}

机构：

[1] Shenyang Inst Chem Technol, Dept Math & Phys, Shenyang 110142, Peoples R China

[2] Liaoning Normal Univ, Chem & Chem Engn Fac, Dalian 116029, Peoples R China

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 2010年 / 944卷 / 1-3期

基金：

美国国家科学基金会;

关键词：

ABEEM-sigma pi model; Ab initio method; Electrophilic additions; Regioselectivity; ELECTRONEGATIVITY EQUALIZATION METHOD; MAXIMUM HARDNESS; SOFT ACIDS; AB-INITIO; PRINCIPLE; REGIOSELECTIVITY;

D O I：

10.1016/j.theochem.2009.12.044

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Electrophilic additions of HCl to a series of asymmetric alkenes in the gas phase have been investigated in the light of the ABEEM-sigma pi model and high-level ab initio method. We demonstrated well the regioselectivity of the electrophilic reactions by means of the ABEEM-sigma pi model on the basis of local HSAB principle and maximum hardness principle. According to the charge distribution in the initial state of alkenes not only regioselectivity has been explained reasonably, but also an interesting phenomenon has been observed that alkenes with electron-donating substituents show a clear regioselectivity, but those with electron-withdrawing ones do not display a clear preference for anti-Markovnikov or Markovnikov addition. Crown Copyright (C) 2010 Published by Elsevier B.V. All rights reserved.

引用

页码：105 / 109

页数：5

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