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Baryshnikov GV, Minaev BF, Pittelkow M, et al. Nucleus-independent chemical shift criterion for aromaticity in π-extended tetraoxa[8]circulenes. J Mol Model. 2012;19(2):847-50doi: 10.1007/s00894-012-1617-7.
Baryshnikov, G. V., Minaev, B. F., Pittelkow, M., Nielsen, C. B., & Salcedo, R. (2013). Nucleus-independent chemical shift criterion for aromaticity in π-extended tetraoxa[8]circulenes. Journal of molecular modeling, 19(2), 847-50. https://doi.org/10.1007/s00894-012-1617-7
Baryshnikov, Gleb V, et al. "Nucleus-independent chemical shift criterion for aromaticity in π-extended tetraoxa[8]circulenes." Journal of molecular modeling vol. 19,2 (2013): 847-50. doi: https://doi.org/10.1007/s00894-012-1617-7
Baryshnikov GV, Minaev BF, Pittelkow M, Nielsen CB, Salcedo R. Nucleus-independent chemical shift criterion for aromaticity in π-extended tetraoxa[8]circulenes. J Mol Model. 2013 Feb;19(2):847-50. doi: 10.1007/s00894-012-1617-7. Epub 2012 Oct 14. PMID: 23065143.
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J Mol Model. 2013 Feb;19(2):847-50. doi: 10.1007/s00894-012-1617-7. Epub 2012 Oct 14.

Nucleus-independent chemical shift criterion for aromaticity in π-extended tetraoxa[8]circulenes.

Journal of molecular modeling

Gleb V Baryshnikov, Boris F Minaev, Michael Pittelkow, Christian B Nielsen, Roberto Salcedo

Affiliations

  1. Bohdan Khmelnytsky National University, 18031, Cherkasy, Ukraine. [email protected]

PMID: 23065143 DOI: 10.1007/s00894-012-1617-7

Abstract

Recently synthesized π-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 Hückel "4n" antiaromaticity rule) that include 8 and 24 π-electrons. Conversely, NICS calculations demonstrated the existence of a common π-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.

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