Abstract
The adaptive natural density partitioning (AdNDP) method has been applied for the first time to porphyrinoids in order to describe their aromaticity. The analysis of π-electron system reveals that aromaticity of annulene originates from 6-π-electron delocalization, while aromaticity of porphyrin can be better described in terms of local aromaticities of the appended 6-π-electron pyrrolic heterocycles and 6-π-electron central fragment. The patterns of chemical bonding for porphyrinoids obtained by AdNDP are consistent with chemical intuition and lead to unique and compact graphic formulas.
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