Local Aromaticity of [n]Acenes, [n]Phenacenes, and [n]Helicenes (n = 1−9).

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Abstract

The local aromaticity of the six-membered rings in three series of benzenoid compounds, namely,\nthe [<i>n</i>]acenes, [<i>n</i>]phenacenes, and [<i>n</i>]helicenes for <i>n</i> = 1−9, has been assessed by means of three\nprobes of local aromaticity based on structural, magnetic, and electron delocalization properties.\nFor [<i>n</i>]acenes our analysis shows that the more reactive inner rings are more aromatic than the\nouter rings. For [<i>n</i>]phenacenes, all indicators of aromaticity show that the external rings are the\nmost aromatic. From the external to the central ring, the local aromaticity varies in a damped\nalternate way. The trends for the [<i>n</i>]helicene series are the same as those found for [<i>n</i>]phenacenes.\nDespite the departure from planarity in [<i>n</i>]helicenes, only a very slight loss of aromaticity is detected\nin [<i>n</i>]helicenes as compared to the corresponding [<i>n</i>]phenacenes. Finally, because of magnetic\ncouplings between superimposed six-membered rings in the higher members of the [<i>n</i>]helicenes\nseries, we have demonstrated that the NICS indicator of aromaticity artificially increases the local\naromaticity of their most external rings.

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