Bond Energy Sums in Benzene, Cyclohexatriene and Cyclohexane Prove Resonance Unnecessary

TL;DR

This paper demonstrates that the observed bond energies in benzene and related compounds can be explained without invoking resonance, challenging traditional views on aromatic stability.

Contribution

It introduces a structural model based on atomic radii differences that accounts for benzene's energy without resonance, offering a new perspective on aromaticity.

Findings

Bond energy sums in benzene align with a non-resonance structure.

The energy of hydrogenation is explained by atomic radii differences.

Resonance is unnecessary to account for benzene's stability.

Abstract

The recent new structure of benzene shows that it consists of three C atoms of radii as in graphite alternating with three C atoms with double bond radii. This is different from the hypothetical cyclohexatriene (Kekule structure) involving alternate double and single bonds. It was shown that the difference in the bond energy sum of the atomic structure of benzene from that of the Kekule structure is the energy (erroneously) assumed to be due to resonance. Here it is shown that the present structure of benzene also explains the energy of hydrogenation into cyclohexane and its difference from that of cyclohexatriene.