Bond Resonance Energy as an Indicator of Local Aromaticity

Abstract

Abstract By definition, bond resonance energy (BRE) represents the contribution of a given π-bond to aromaticity. The minimum BRE in a π-system is an excellent measure of kinetic stability. It was found that the BRE for a peripheral π-bond correlated not only to the harmonic oscillator model of aromaticity (HOMA) index for a ring, to which the π-bond belongs, but also to the corresponding bond-order index of aromaticity (BOIA) for local aromaticity. Thus, the BRE for a peripheral π-bond can be used as an energetic indicator of local aromaticity at least for polycyclic aromatic hydrocarbons (PAHs).