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Structure, aromaticity and reactivity of corannulene and its analogues: a conceptual density functional theory and density functional reactivity theory study.
- Source :
-
Molecular Physics . Apr2018, Vol. 116 Issue 7/8, p956-968. 13p. - Publication Year :
- 2018
-
Abstract
- Corannulene is an interesting yet special molecule, which has witnessed widespread applications. It is aromatic, but not planar and the total number of 20 π electrons is in conflict with Hückel's 4<italic>n</italic> + 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00268976
- Volume :
- 116
- Issue :
- 7/8
- Database :
- Academic Search Index
- Journal :
- Molecular Physics
- Publication Type :
- Academic Journal
- Accession number :
- 129037871
- Full Text :
- https://doi.org/10.1080/00268976.2017.1403657