Nucleus-independent chemical shift criterion for aromaticity in pi-extended tetraoxacirculenes
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
Recently synthesized pi-extended symmetrical tetraoxacirculenes 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 tetraoxacirculene 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 tetraoxacirculene molecules. Thus, these symmetrical tetraoxacirculene 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.
Tetraoxacirculenes, Aromaticity, Antiaromaticity, Huckel rule, NICS indices, Cyclooctatetraene ring
Biochemistry and Molecular Biology
IdentifiersURN: urn:nbn:se:kth:diva-118601DOI: 10.1007/s00894-012-1617-7ISI: 000314051200035ScopusID: 2-s2.0-84877114959OAI: oai:DiVA.org:kth-118601DiVA: diva2:607203
QC 201302222013-02-222013-02-212013-02-22Bibliographically approved