A case of breakdown of the Kekulé-structure model(Article)
- Faculty of Science, University of Kragujevac, P. O. Box 60, 34000 Kragujevac, Serbia
Abstract
For a long time, Kekulé structures have been used to predict and rationalize the stability, geometry, and π-electron properties of polycyclic conjugated molecules, especially hydrocarbons. We now point out an example, demonstrating that the Kekulé-structure model is not generally applicable. Namely, the molecule of dibenzo[cd,mn]indeno[123, gf ]pyrene is perfectly planar and strain-free. Yet, its geometry (determined by means of an unrestricted symmetry-broken UB3LYP/6-311G(d,p) DFT method) is in complete disagreement with what one would expect on the basis of its Kekulé structures. © Taylor & Francis Group, LLC.
Indexed keywords
| Engineering controlled terms: | Molecules |
|---|---|
| Engineering uncontrolled terms | Conjugated moleculesDouble bondsElectron propertiesFluoranthenesKekulé structureLocalisedLocalized double bondMolecular geometriesStructure modelsπ-electrons |
| Engineering main heading: | Geometry |
- ISSN: 10406638
- Source Type: Journal
- Original language: English
- DOI: 10.1080/10406638.2010.503162
- Document Type: Article
- Publisher: Taylor and Francis Inc.
Gutman, I.; Faculty of Science, University of Kragujevac, P. O. Box 60, Serbia;
© Copyright 2024 Elsevier B.V., All rights reserved.
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