期刊
MOLECULAR PHYSICS
卷 116, 期 7-8, 页码 956-968出版社
TAYLOR & FRANCIS LTD
DOI: 10.1080/00268976.2017.1403657
关键词
Aromaticity; corannulene; coronene; conceptual density functional theory; density functional reactivity theory
资金
- National Natural Science Foundation of China [21503076]
- Hunan Provincial Natural Science Foundation of China [2017JJ3201]
- Hunan Provincial Innovation Foundation for Postgraduates [CX2017B179]
- China Scholarship Council [201706720015]
Corannulene is an interesting yet special molecule, which has witnessed widespread applications. It is aromatic, but not planar and the total number of 20 electrons is in conflict with Huckel's 4n + 2 rule. In this work, we design a series of analogous model systems based on this molecule with the central ring size extended from five members to three to eight members. A number of theoretical and analytical tools available in the literature are employed to systematically examine their structure, aromaticity and reactivity properties. We found that structurally speaking, they change from bowl-like to planar and then to saddle shapes as the central ring size increases from three to eight. From the reactivity perspective, species with five and six-membered-rings in the centre are chemically more stable and less reactive, which are confirmed by the numerical results from aromaticity indexes and quantities from the information-theoretic approach. Overall, our results show that only corannulene and its six-membered-ring, coronene, analogue are aromatic. Even though these two systems are aromatic in nature, they are markedly different in a number of ways in structure, reactivity and other properties. These results should provide with us insights and understanding about the phenomenon of three-dimensional and non-planarity aromaticity.
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