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Nucleus-independent chemical shift criterion for aromaticity in pi-extended tetraoxa[8]circulenes
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
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2013 (English)In: Journal of Molecular Modeling, ISSN 1610-2940, E-ISSN 0948-5023, Vol. 19, no 2, 847-850 p.Article in journal (Refereed) Published
Abstract [en]

Recently synthesized pi-extended symmetrical tetraoxa[8]circulenes that exhibit electroluminescent properties were calculated at the density functional theory (DFT) level using the quantum theory of atoms in molecules (QTAIM) approach to electron density distribution analysis. Nucleus-independent chemical shift (NICS) indices were used to characterize the aromaticity of the studied molecules. The tetraoxa[8]circulene molecules were found to consist of two antiaromatic perimeters (according to the Huckel "4n" antiaromaticity rule) that include 8 and 24 pi-electrons. Conversely, NICS calculations demonstrated the existence of a common pi-extended system (distributed like a flat ribbon) in the studied tetraoxa[8]circulene molecules. Thus, these symmetrical tetraoxa[8]circulene molecules provide examples of diatropic systems characterized by the presence of induced diatropic ring currents.

Place, publisher, year, edition, pages
2013. Vol. 19, no 2, 847-850 p.
Keyword [en]
Tetraoxa[8]circulenes, Aromaticity, Antiaromaticity, Huckel rule, NICS indices, Cyclooctatetraene ring
National Category
Biochemistry and Molecular Biology
URN: urn:nbn:se:kth:diva-118601DOI: 10.1007/s00894-012-1617-7ISI: 000314051200035ScopusID: 2-s2.0-84877114959OAI: diva2:607203

QC 20130222

Available from: 2013-02-22 Created: 2013-02-21 Last updated: 2013-02-22Bibliographically approved

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Minaev, Boris F.
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