Abstract
AbstractRecently, it was claimed that D4h‐1,3,5,7‐cyclooctatetraene (2) is nonaromatic, according to a definition of aromaticity, which relies of the behavior of excited states. This conclusion is based mainly on MCD studies of tetrakis[2.1.1]bicyclohexano‐1,3,5,7‐cyclooctatetraene (1) and computational work on 2 at different symmetries. In this work, the aromaticity of 2 is studied by ground state criteria—aromatic stabilization energy (ASE) and magnetic properties. The ASE of 2 is studied and compared with those of benzene and cyclobutadiene. NICS(1)π,zz studies of 1 and 2 and comparison with tris‐bicyclo[2.1.1]hexanobenzene and benzene suggests a dramatic reduction of ring currents in the annulated systems. The reason was found to be mixing of the p orbitals of the bridgehead carbon atoms into the central rings π systems. It is unclear whether 2 should be considered antiaromatic, nonaromatic, or aromatic, but it is clear that 1 is not a good model for 2 for aromaticity studies purposes according to ground‐state properties (energy and magnetic).
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