Nucleus independent chemical shift calculations on bis-indenylidene dications suggest that these dications possess substantial antiaromaticity and that changes that affect patterns of delocalization can have dramatic effects on their antiaromaticity, as shown for 12+  and 22+  . Phenyl substituents can also perturb the delocalization patterns, resulting in changes in the magnitude of the antiaromaticity of these systems, as shown for 32+  -62+ .The synthesis of the dication precursors will be described. We will discuss catalysts systems for the coupling reaction as well as the effect of the halogen and steric hindrance on that coupling.

Using substituents to modify antiaromaticity in bis-indenylidene dications: The effect of different patterns of delocalization

245th National Meeting (2013)

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