Is coronene better described by Clar's aromatic π-sextet model or by the AdNDP representation?
© 2017 Wiley Periodicals, Inc.
| Veröffentlicht in: | Journal of computational chemistry. - 1984. - 38(2017), 18 vom: 05. Juli, Seite 1606-1611 |
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| Format: | Online-Aufsatz |
| Sprache: | English |
| Veröffentlicht: |
2017
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| Zugriff auf das übergeordnete Werk: | Journal of computational chemistry |
| Schlagworte: | Journal Article Research Support, Non-U.S. Gov't nucleus independent chemical shift Clar's aromatic π-sextet Diels-Alder adaptative natural density partitioning aromatic fluctuation index harmonic oscillator model of aromaticity para-delocalization index |
| Zusammenfassung: | © 2017 Wiley Periodicals, Inc. The bonding patterns in coronene are complicated and controversial as denoted by the lack of consensus of how its electronic structure should be described. Among the different proposed descriptions, the two most representative are those generated by Clar's aromatic π-sextet and adaptative natural density partitioning (AdNDP) models. Quantum-chemical calculations at the density functional theory level are performed to evaluate the model that gives a better representation of coronene. To this end, we analyse the molecular structure of coronene, we estimate the aromaticity of its inner and outer rings using various local aromaticity descriptors, and we assess its chemical reactivity from the study of the Diels-Alder reaction with cyclopentadiene. Results obtained are compared with those computed for naphthalene and phenanthrene. Our conclusion is that Clar's π-sextet model provides the representation of coronene that better describes the physicochemical behavior of this molecule. © 2017 Wiley Periodicals, Inc |
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| Beschreibung: | Date Revised 20.11.2019 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
| ISSN: | 1096-987X |
| DOI: | 10.1002/jcc.24801 |