Deciphering aromaticity in porphyrinoids via adaptive natural density partitioning

Org Biomol Chem. 2014 Aug 28;12(32):6145-50. doi: 10.1039/c4ob01018c. Epub 2014 Jul 8.

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.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Algorithms
  • Electrons
  • Models, Molecular*
  • Porphyrins / chemistry*
  • Quantum Theory*

Substances

  • Porphyrins