Direct evaluation of the induced π current density in [5]paracyclophane (1) shows that, despite the significant non-planarity (α = 23.2°) enforced by the pentamethylene bridge, there is only a modest (ca. 17%) reduction in the π ring current, justifying the use of shielding-cone arguments for the assignment of 1H NMR chemical shifts of 1 and the claim that the non-planar benzene ring in 1 retains its aromaticity (on the magnetic criterion). © 2011 The Owner Societies.
Aromaticity of strongly bent benzene rings: Persistence of a diatropic ring current and its shielding cone in [5]paracyclophane
Soncini A.;
2011
Abstract
Direct evaluation of the induced π current density in [5]paracyclophane (1) shows that, despite the significant non-planarity (α = 23.2°) enforced by the pentamethylene bridge, there is only a modest (ca. 17%) reduction in the π ring current, justifying the use of shielding-cone arguments for the assignment of 1H NMR chemical shifts of 1 and the claim that the non-planar benzene ring in 1 retains its aromaticity (on the magnetic criterion). © 2011 The Owner Societies.File in questo prodotto:
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