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Is benzene oxide homoaromatic? A microcalorimetric study.

Z S Jia¹, P Brandt, A Thibblin

¹Contribution from the Institute of Chemistry, University of Uppsala, Box 531, S-751 21 Uppsala, Sweden.

Journal of the American Chemical Society

|October 18, 2001

Summary

Benzene oxide exhibits unusual stability due to homoaromatization, explaining its low reactivity in acid-catalyzed reactions. This thermodynamic stability is key to understanding its chemical behavior.

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Area of Science:

Physical organic chemistry
Computational chemistry
Reaction kinetics

Background:

Aromatization reactions are fundamental in organic chemistry.
Benzene oxide and benzene hydrate are key intermediates in understanding aromaticity.
Previous studies suggested homoaromatic stabilization in benzene oxide.

Purpose of the Study:

To measure reaction enthalpies and rate constants for benzene oxide and benzene hydrate aromatization.
To compare the thermodynamic stability and reactivity of these compounds.
To elucidate the factors contributing to benzene oxide's unusual stability and low reactivity.

Main Methods:

Heat-flow microcalorimetry was used to measure reaction enthalpies.
B3LYP hybrid functional calculations with AM1/SM2 solvation corrections were employed.
Comparison with related cyclohexadiene oxide and cyclohexenol reactions.

Main Results:

Benzene oxide's heat of reaction (ΔH = -57.0 kcal mol⁻¹) is significantly larger than benzene hydrate's (ΔH = -38.7 kcal mol⁻¹).
Benzene oxide shows unusually low reactivity (rate ratio 0.08) compared to its thermodynamic driving force.
Calculated and measured enthalpies align, supporting homoaromatic stabilization in benzene oxide.

Conclusions:

Benzene oxide is significantly stabilized by homoaromatization, accounting for its reduced reactivity.
This unusual stability explains over half of the observed 10⁷-fold lower than expected reactivity.
The remaining decrease in reactivity is attributed to a high-energy carbocation-forming transition state.