Calculation of the molecule of coronene-10,5 (C30H10)

Bochvar, D. A.; Gal’pern, E. G.; Gambaryan, N. P.

doi:10.1007/bf00853389

Cited by 5 publications

(10 citation statements)

References 1 publication

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“…2). 14,15,17 This yet elusive molecule has four Kekulé structures with all spokes always being formal single bonds. Thus, inner and outer cycles are formally decoupled, suggesting that an AWA picture of electronic structure might be applicable to 2.…”

Section: Kekulene and The Awa Modelmentioning

confidence: 99%

“…36 As already stated, the paramagnetic current induced along the hub cycle in 1 does not conform to the AWA model. [14,7]Coronene and the AWA model [14,7]Coronene (3 in Fig. 2) was theoretically designed by Dickens and Mallion.…”

Section: Kekulene and The Awa Modelmentioning

confidence: 99%

“…However, if not, many circuits that extend over the hub and rim will play a dominant role in aromatic stabilization 12,13 and invalidate the AWA picture. Some candidates for the AWA model, such as [10,5]- (2), [14,7]- (3), [8,5]-(4) and [12,5] coronenes (5), have recently been proposed (see Fig. 2 and 3 for their molecular structures).…”

Section: Introductionmentioning

confidence: 99%

“…2 and 3 for their molecular structures). [14][15][16][17][18] Coronene (6) and corannulene (7) have likewise been considered as candidates for the AWA bonding model (Fig. 4).…”

Section: Introductionmentioning

confidence: 99%

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Validity and limitations of the annulene-within-an-annulene (AWA) model for macrocyclic π-systems

Aihara

2014

RSC Adv.

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Section: Kekulene and The Awa Modelmentioning

confidence: 99%

Section: Kekulene and The Awa Modelmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…2 and 3 for their molecular structures). [14][15][16][17][18] Coronene (6) and corannulene (7) have likewise been considered as candidates for the AWA bonding model (Fig. 4).…”

Section: Introductionmentioning

confidence: 99%

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Validity and limitations of the annulene-within-an-annulene (AWA) model for macrocyclic π-systems

Aihara

2014

RSC Adv.

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“…In search of AWA structures, theoretical studies have been performed for the all-five-membered ring (i. e., cyclopenta) analogues of [10]circulene and [8]circulene, called [10.5] coronene [31][32][33] and [8.5]coronene, [34] respectively (Figure 2). Indeed, these molecules are predicted to adopt AWA structures consisting of aromatic 10 π-electron and antiaromatic 20 πelectron circuits in the former and antiaromatic 8 πand 20 πelectron circuits in the latter.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structures of Tetramesityl‐Substituted Tetracyclopenta[def,jkl,pqr,vwx]tetraphenylene

2021

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Crystal structures of tetramesityl-substituted tetracyclopenta [def,jkl,pqr,vwx]tetraphenylene (TCPTP) derivative were determined for crystals containing different solvents, CHCl 3 , CH 2 Cl 2 , acetone, and benzene at different temperatures to discuss the conjugation modes in the antiaromatic system, i. e., whether it adopts a D 2h structure consisting of local aromatic sextets and quinodimethane substructures or a D 4h double annulenenoid structure. The structures of the TCPTP core in all crystals determined at 113 K or 93 K resemble those of the theoretical D 2h geometry, whereas the bond lengths at room temperature (293 K) adopt averaged values of the theoretical D 2h and D 4h geometries. These results are interpreted in terms of disorder of two perpendicularly oriented D 2h structures at room temperature and support the theoretical prediction which favours the D 2h geometry. The slightly different bond length distributions in the crystals are ascribed to the different space in the vicinity of the molecule which allows the molecule to adopt the two orientations in different occupancies.

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The Impact of Antiaromatic Subunits in [4n+2] π-Systems: Bispentalenes with [4n+2] π-Electron Perimeters and Antiaromatic Character

et al. 2015

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Three series of stable, neutral, π-extended bispentalene derivatives, with two pentalenes fused to a central benzene or naphthalene moiety, have been prepared through a modified double carbopalladation cascade reaction. While these chromophores feature skeletons with [4n+2] π-electron perimeters, the two 8 π-electron pentalene subunits strongly influence bonding and spectral properties. (1)H NMR spectra showed large upfield shifts of the protons in the pentalene moieties, comparable to antiaromatic monobenzopentalenes. Further investigations on magnetic ring currents through NICS-XY-scans suggest a global paratropic current and a local diatropic current at the central benzene ring in two of the series, while the third series, with a central naphthalene ring, showed more localized ring currents, with stronger paratropic ring currents on the pentalene moieties. X-ray diffraction analyses revealed planar bispentalene cores with large double- and single-bond alternation in the pentalene units, characteristic for antiaromaticity, and small alternation in the central aromatic rings. In agreement with TD-DFT calculations, both optical and electrochemical data showed much smaller HOMO-LUMO energy gaps compared to other neutral, acene-like hydrocarbons with the same number of fused rings. Both experimental and computational results suggest that the molecular properties of the presented bispentalenes are dominated by the antiaromatic pentalene-subunits despite the [4n+2] π-electron perimeter of the skeletons.

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Calculation of the molecule of coronene-10,5 (C30H10)

Cited by 5 publications

References 1 publication

Validity and limitations of the annulene-within-an-annulene (AWA) model for macrocyclic π-systems

Validity and limitations of the annulene-within-an-annulene (AWA) model for macrocyclic π-systems

Crystal Structures of Tetramesityl‐Substituted Tetracyclopenta[def,jkl,pqr,vwx]tetraphenylene

The Impact of Antiaromatic Subunits in [4n+2] π-Systems: Bispentalenes with [4n+2] π-Electron Perimeters and Antiaromatic Character

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