Aromaticity of the planar hetero[8]circulenes and their doubly charged ions: NICS and GIMIC characterization

被引:68
作者
Baryshnikov, G. V. [1 ]
Valiev, R. R. [2 ,3 ]
Karaush, N. N. [1 ]
Minaev, B. F. [1 ,2 ]
机构
[1] Bohdan Khmelnytsky Natl Univ, UA-18031 Cherkassy, Ukraine
[2] Tomsk State Univ, Tomsk 634050, Russia
[3] Natl Res Tomsk Polytech Univ, Tomsk 634050, Russia
关键词
INDEPENDENT CHEMICAL-SHIFTS; MOLECULAR-ORBITAL METHODS; ELECTRONIC-PROPERTIES; CURRENT DENSITIES; BASIS-SET; DESIGN; MODEL;
D O I
10.1039/c4cp00860j
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
A series of planar hetero[8] circulenes and their doubly charged ions are studied by the NICS and GIMIC methods to interpret the aromatic properties of these high symmetry species. In accordance with the performed calculations all studied hetero[8] circulenes are found to be nonaromatic compounds because paratropic and diatropic ring-currents are completely canceled yielding almost zero net current. In great contrast, the dicationic and dianionic hetero[8] circulenes demonstrate the predominant contribution of diatropic ring currents resulting in the total aromatic character of the studied doubly charged ions. This fact allows us to predict the high stability of dianionic hetero[8] circulenes and explains the extremely high stability of dicationic species observed in the mass-spectra.
引用
收藏
页码:15367 / 15374
页数:8
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