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

Department of Chemistry

41 Citations (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.]

Original language	English
Journal	Journal of Molecular Modeling
Volume	19
Issue number	2
Pages (from-to)	847-850
Number of pages	4
ISSN	1610-2940
DOIs	https://doi.org/10.1007/s00894-012-1617-7
Publication status	Published - Feb 2013

Access to Document

10.1007/s00894-012-1617-7

Cite this

@article{b66f5cf65973494bbf52e9bdda6889ac,

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.]",

author = "Baryshnikov, {Gleb V.} and Minaev, {Boris F.} and Michael Pittelkow and Nielsen, {Christian Benedikt} and Roberto Salcedo",

year = "2013",

month = feb,

doi = "10.1007/s00894-012-1617-7",

language = "English",

volume = "19",

pages = "847--850",

journal = "Journal of Molecular Modeling",

issn = "1610-2940",

publisher = "Springer",

number = "2",

}

TY - JOUR

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.]

U2 - 10.1007/s00894-012-1617-7

DO - 10.1007/s00894-012-1617-7

M3 - Journal article

C2 - 23065143

SN - 1610-2940

VL - 19

SP - 847

EP - 850

JO - Journal of Molecular Modeling

JF - Journal of Molecular Modeling

IS - 2

ER -

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

Abstract

Access to Document

Fingerprint

Cite this