Deciphering aromaticity in porphyrinoids via adaptive natural density partitioning†
Alexander S. Ivanov,Alexander I. Boldyrev
Organic & Biomolecular Chemistry Pub Date : 07/01/2014 00:00:00 , DOI:10.1039/C4OB01018C
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.

Graphical abstract: Deciphering aromaticity in porphyrinoids via adaptive natural density partitioning