Abstract
An empirical valence bond structure-resonance theory is applied to monocyclic oxocarbon dianions and neutral oxocarbons. Graph theoretical techniques are used to carry out the calculations. The resonance energies are partitioned among various types of resonance interactions. Carbonyl group covalent-ionic resonance is the most prevalent type of stabilizing resonance term in every case (⩾50%). Resonance energies, charge distributions, and bond orders are compared with the results of MO calculations, and with relevant experimental data. A qualitative valence bond interpretation of the concept of aromaticity is proposed based on cyclic terms that appear in the graph of the empirical structure-resonance theory Hamiltonian matrix. On this basis, all oxocarbon dianions are found to be resonance stabilized and aromatic, whereas the neutral oxocarbons are nonaromatic but still stabilized by resonance.
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