Aromaticity appears to be among the most controversial concepts in modern chemistry. The present paper addresses current controversies in development and applications of the two main criteria of aromaticity, namely, energetic and structural criteria. Various types of resonance energy with an emphasis on homodesmotic and isodesmic stabilization energies have been discussed. Reliability of such structural criteria of aromaticity as equalization of carbon-carbon bond lengths and stability with respect to out-of-plane distortions of a molecular structure has been analyzed using various examples.
No takes yet. Share an insight, caveat, or question.
Mikhail N. Glukhovtsev (1997) studied this question.