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

Gleb V. Baryshnikov; Boris F. Minaev; Michael Pittelkow; Christian Benedikt Nielsen; Roberto Salcedo

doi:10.1007/s00894-012-1617-7

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

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

Kemisk Institut

41 Citationer (Scopus)

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. [Figure not available: see fulltext.]

Originalsprog	Engelsk
Tidsskrift	Journal of Molecular Modeling
Vol/bind	19
Udgave nummer	2
Sider (fra-til)	847-850
Antal sider	4
ISSN	1610-2940
DOI	https://doi.org/10.1007/s00894-012-1617-7
Status	Udgivet - feb. 2013

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10.1007/s00894-012-1617-7

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title = "Nucleus-independent chemical shift criterion for aromaticity in π-extended tetraoxa[8]circulenes",

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 H{\"u}ckel {"}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. [Figure not available: see fulltext.]",

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T1 - Nucleus-independent chemical shift criterion for aromaticity in π-extended tetraoxa[8]circulenes

AU - Baryshnikov, Gleb V.

AU - Minaev, Boris F.

AU - Pittelkow, Michael

AU - Nielsen, Christian Benedikt

AU - Salcedo, Roberto

PY - 2013/2

Y1 - 2013/2

N2 - 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. [Figure not available: see fulltext.]

AB - 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. [Figure not available: see fulltext.]

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DO - 10.1007/s00894-012-1617-7

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EP - 850

JO - Journal of Molecular Modeling

JF - Journal of Molecular Modeling

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ER -

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

Abstract

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