An Insight into the Local Aromaticities of Polycyclic Aromatic Hydrocarbons and Fullerenes

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Abstract
In this work we quantify the local aromaticity of six-membered rings in a series of planar and bowl-shaped polycyclic aromatic hydrocarbons (PAHs) and fullerenes. The evaluation of local aromaticity has been carried out through the use of structurally (HOMA) and magnetically (NICS) based measures, as well as by the use of a new electronically based indicator of aromaticity, the para delocalization index (PDI), which is defined as the average of all the Bader delocalization indices between para-related carbon atoms in six-membered rings. The series of PAHs selected includes C10H8, C12H8, C14H8, C20H10, C26H12, and C30H12, with benzene and C60 taken as references. The change in the local aromaticity of the six-membered rings on going from benzene to C60 is analyzed. Finally, we also compare the aromaticity of C60 with that of C70, open [5,6]- and closed [6,6]-C60NH systems, and C60F18.