对多环芳烃和富勒烯局部芳香性的深入研究。

An insight into the local aromaticities of polycyclic aromatic hydrocarbons and fullerenes.

作者信息

Poater Jordi, Fradera Xavier, Duran Miquel, Solà Miquel

机构信息

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

出版信息

Chemistry. 2003 Mar 3;9(5):1113-22. doi: 10.1002/chem.200390128.

DOI:10.1002/chem.200390128

PMID:12596147

Abstract

In this work we quantify the local aromaticity of six-membered rings in a series of planar and bowl-shaped polycyclic aromatic hydrocarbons (PAHs) and fullerenes. The evaluation of local aromaticity has been carried out through the use of structurally (HOMA) and magnetically (NICS) based measures, as well as by the use of a new electronically based indicator of aromaticity, the para delocalization index (PDI), which is defined as the average of all the Bader delocalization indices between para-related carbon atoms in six-membered rings. The series of PAHs selected includes C(10)H(8), C(12)H(8), C(14)H(8), C(20)H(10), C(26)H(12), and C(30)H(12), with benzene and C(60) taken as references. The change in the local aromaticity of the six-membered rings on going from benzene to C(60) is analyzed. Finally, we also compare the aromaticity of C(60) with that of C(70), open [5,6]- and closed [6,6]-C(60)NH systems, and C(60)F(18).

摘要

在这项工作中，我们对一系列平面和碗状多环芳烃（PAHs）及富勒烯中六元环的局部芳香性进行了量化。局部芳香性的评估通过基于结构的（HOMA）和基于磁性的（NICS）方法进行，同时还使用了一种新的基于电子的芳香性指标——对位离域指数（PDI），其定义为六元环中对位相关碳原子之间所有巴德离域指数的平均值。所选的PAHs系列包括C(10)H(8)、C(12)H(8)、C(14)H(8)、C(20)H(10)、C(26)H(12)和C(30)H(12)，以苯和C(60)作为参考。分析了从苯到C(60)过程中六元环局部芳香性的变化。最后，我们还比较了C(60)与C(70)、开环[5,6]-和闭环[6,6]-C(60)NH体系以及C(60)F(18)的芳香性。