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Issue 17, 2016
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Aromatic stabilization of functionalized corannulene cations

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Abstract

The first comprehensive theoretical investigation of aromaticity in functionalized corannulene cations of general formula [CH3–C20H10]+ was accomplished. The experimentally known system [CH3-hub-C20H10]+ was augmented by two other possible isomers, namely, rim- and spoke-ones. Changes in aromaticity, when going from neutral corannulene to its functionalized cations, were monitored with the help of descriptors of different nature such as structure-based HOMA, topological PDI and FLU, and magnetic NICS. A highly efficient tool for analysis and visualization of delocalization and conjugation named ACID was also utilized. In the final step, a complete set of 1H and 13C chemical shifts was calculated and compared with the available experimental data. Conservation of aromaticity of 6-membered rings along with vanishing anti-aromatic character of central 5-membered rings was found to be the main reason for the exceptional stability of the hub-isomer. At the same time, functionalization of the corannulene moiety at the rim- or spoke-site resulted in dramatic elimination of aromaticity of 6-membered rings, whereas anti-aromatic character of the central ring remained. Altogether, it led to much lower stability of these isomers in comparison with that of the hub-one.

Graphical abstract: Aromatic stabilization of functionalized corannulene cations

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Publication details

The article was received on 15 Nov 2015, accepted on 05 Jan 2016 and first published on 07 Jan 2016


Article type: Paper
DOI: 10.1039/C5CP07002C
Author version available: Download Author version (PDF)
Citation: Phys. Chem. Chem. Phys., 2016,18, 11781-11791
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    Aromatic stabilization of functionalized corannulene cations

    J. Li and A. Yu. Rogachev, Phys. Chem. Chem. Phys., 2016, 18, 11781
    DOI: 10.1039/C5CP07002C

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