Aromatic stabilization of functionalized corannulene cations

Physical Chemistry Chemical Physics : PCCP
Jingbai Li, Andrey Yu Rogachev

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 (1)H and (13)C 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...Continue Reading

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Citations

Jul 19, 2016·Journal of Computational Chemistry·Jingbai LiAndrey Yu Rogachev
Aug 3, 2017·Physical Chemistry Chemical Physics : PCCP·Qi XuAndrey Yu Rogachev
Jun 20, 2018·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Shuyang Liu, Andrey Yu Rogachev
Oct 12, 2018·Journal of Computational Chemistry·Jingbai LiAndrey Yu Rogachev
Mar 13, 2020·Physical Chemistry Chemical Physics : PCCP·Melisa Alkan, Andrey Yu Rogachev
Sep 10, 2019·Journal of Computational Chemistry·Jingbai Li, Andrey Yu Rogachev

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