通过电子离域化措施对休克尔[4n + 2]规则的分析。

Analysis of Hückel's [4n + 2] rule through electronic delocalization measures.

作者信息

Feixas Ferran, Matito Eduard, Solà Miquel, Poater Jordi

机构信息

Institut de Química Computacional and Departament de Química, Campus de Montilivi, 17071 Girona, Catalonia, Spain.

出版信息

J Phys Chem A. 2008 Dec 18;112(50):13231-8. doi: 10.1021/jp803745f.

DOI:10.1021/jp803745f

PMID:18834099

Abstract

In the present work, we analyze the pi-electronic delocalization in a series of annulenes and their dications and dianions by using electron delocalization indices calculated in the framework of the quantum theory of atoms in molecules. The aim of our study is to discuss the Hückel's 4n + 2 rule from the viewpoint of pi-electronic delocalization. Our results show that there is an important increase of electronic delocalization (of about 1 e) when going from antiaromatic 4n pi systems to aromatic (4n + 2)pi systems. Less clear is the change in pi-electronic delocalization when we move from a (4n + 2)pi-aromatic to a 4n pi-antiaromatic species by adding or removing a pair of electrons.

摘要

在本工作中，我们通过使用在分子中原子的量子理论框架下计算的电子离域指数，分析了一系列轮烯及其双阳离子和双阴离子中的π电子离域。我们研究的目的是从π电子离域的角度讨论休克尔4n + 2规则。我们的结果表明，从反芳香性的4nπ体系转变为芳香性的(4n + 2)π体系时，电子离域有显著增加（约1个电子）。当我们通过添加或移除一对电子，从(4n + 2)π芳香性物种转变为4nπ反芳香性物种时，π电子离域的变化则不太明显。