The trouble with resonance energies: A Hückel theory topic

Abstract

Resonance energies are shown to be quasithermodynamic in character. Hence, they are generally unsuitable as bases for anticipating kinetic stabilities. Examples are provided, leading to the conclusion that those who intend the word 'aromatic' to mean chemically unreactive, need to carry out full Hückel calculations in order to rank hydrocarbons using the frontier orbital energies.