articleThe Journal of Organic ChemistryJan 30, 2002Closed access

To What Extent Can Aromaticity Be Defined Uniquely?

Friedrich-Alexander-Universität Erlangen-Nürnberg · University of Warsaw · +2 more institutions

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Abstract

Statistical analyses of quantitative definitions of aromaticity, ASE (aromatic stabilization energies), RE (resonance energies), Lambda (magnetic susceptibility exaltation), NICS, HOMA, I5, and A(J), evaluated for a set of 75 five-membered pi-electron systems: aza and phospha derivatives of furan, thiophene, pyrrole, and phosphole (aromatic systems), and a set of 30 ring-monosubstituted compounds (aromatic, nonaromatic, and antiaromatic systems) revealed statistically significant correlations among the various aromaticity criteria, provided the whole set of compounds is involved. Hence, broadly considered, the various manifestations of aromaticity are related and aromaticity can be regarded statistically as a…

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