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. 2008 Dec 18;10(24):5573-6.
doi: 10.1021/ol802417n.

Stacked-ring aromaticity: an orbital model

D E Bean  1 , P W Fowler
Affiliations

Stacked-ring aromaticity: an orbital model

D E Bean et al. Org Lett. .

Abstract

Visualization of induced current density using the ipsocentric CHF/CTOCD-DZ/6-31G** approach gives a direct demonstration of the literature proposal of reversal of [4n]annulene antiaromaticity on stacking cyclooctatetraene (COT) rings into a superphane. Through-space interactions lead to a closed-shell in which paratropicity of planar COT units is quenched, and layered diatropic currents arise from magnetic response of two pairs of frontier orbitals. A general orbital model rationalizes the differences in current between stacked aromatic and antiaromatic rings.

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