Journal article

Currents in tangentially p-p bonded sigma-aromatic systems

Patrick W Fowler, Agnieszka Rogowska, Alessandro Soncini, Mark Lillington, Leif P Olson

JOURNAL OF ORGANIC CHEMISTRY | AMER CHEMICAL SOC | Published : 2006

Abstract

We report a theoretical study of ring systems that delocalize electrons in a cyclic array of p orbitals arranged tangentially in sigma-bonding fashion. Sigma-bonded arrays are compared to conventional pi-bonded analogues with respect to orbital symmetry and aromatic/antiaromatic behavior. In a one-to-one correspondence between pi and tangential molecular orbitals of a cycle, local rotation turns each pi to a tangential basis function, changing bonding interactions to antibonding and inverting the order of filling of molecular orbitals. The ipsocentric ring-current mapping approach is used to evaluate aromaticity on the magnetic criterion. As for conventional pi-ring currents, the sigma-ring ..

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University of Melbourne Researchers