亲电取代反应中活性位点预测方法的比较

doi:10.3866/PKU.WHXB201401211

Abstract

Abstract:

Predicting the reactivity of electrophilic substitution at different sites is of theoretical and practical significance, and many prediction methods based on the electronic structure of reactants have been proposed. We compared the reliability of 14 prediction methods, using 14 monosubstituted and 8 disubstituted benzenes as test sets. Methods reflecting local electronic softness, such as the Fukui function and average local ionization energy, are well-suited to monosubstituted benzenes with ortho-para directing groups and disubstituted benzenes. However, these methods often fail for systems containing a single meta directing group. Methods reflecting electrostatic effects perform worse overall than those reflecting local softness, but are better suited to systems containing a single meta directing group. Dual descriptor is the most overall robust method, and can be regarded as a universal prediction method.

Key words: Electrophilic substitution, Molecular surface, Fukui function, Dual descriptor, Electrostatic potential, Atomic charge, Orbital composition

MSC2000:

O641

FU Rong, LU Tian, CHEN Fei-Wu. Comparing Methods for Predicting the Reactive Site of Electrophilic Substitution[J].Acta Phys. -Chim. Sin., 2014, 30(4): 628-639.

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Comparing Methods for Predicting the Reactive Site of Electrophilic Substitution

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