Exploring the validity of the Glidewell-Lloyd extension of Clar's π-sextet rule: assessment from polycyclic conjugated hydrocarbons

被引：25

作者：

El Bakouri, Ouissam ^{[1
,2
]}

Poater, Jordi ^{[3
,4
,5
]}

Feixas, Ferran ^{[1
,2
]}

Sola, Miquel ^{[1
,2
]}

机构：

[1] Univ Girona, IQCC, Girona 17003, Spain

[2] Univ Girona, Dept Quim, Girona 17003, Spain

[3] Univ Barcelona, Dept Quim Inorgan & Organ, Barcelona 08028, Catalonia, Spain

[4] Univ Barcelona, Inst Quim Teor & Computac IQTCUB, Barcelona 08028, Catalonia, Spain

[5] ICREA, Barcelona 08010, Catalonia, Spain

来源：

THEORETICAL CHEMISTRY ACCOUNTS | 2016年 / 135卷 / 08期

关键词：

Glidewell-Lloyd's rule; Clar's pi-sextet rule; Polycyclic conjugated hydrocarbons; Aromaticity; Clamped benzenes; Double bonds in ring junctions; MULTICENTER BOND INDEXES; ELECTRON DELOCALIZATION; QUANTUM CONTRIBUTIONS; MOLECULAR-STRUCTURE; AROMATIC-MOLECULES; LOCAL AROMATICITY; CLAMPED BENZENES; DENSITY; LOCALIZATION; STATE;

D O I：

10.1007/s00214-016-1970-1

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：

The Clar pi-sextet rule was formulated as a tool to qualitatively assign the local aromatic character of six-membered rings in benzenoid species. This simple rule has been widely validated both experimentally and theoretically. In 1984, Glidewell and Lloyd reported an extension of this rule to polycyclic conjugated hydrocarbons having rings with any even number of carbon atoms in their structure. In this work, we assess the validity of the Glidewell-Lloyd extension in 69 polycyclic conjugated hydrocarbons composed of different combinations of four-, six-, and eight-membered rings. Our results support the validity of this extension with some exceptions that are discussed. Finally, a minor modification to the rule is proposed.

引用

页数：12