The resonance energy of a compound is a measure
of the extra stability of the conjugated system compared to the corresponding
number of isolated double bonds. This can be calculated from experimental
measurements.
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The diagram shows the experimental heats of hydrogenation, DHh,
for three molecules, benzene, 1,3-cyclohexadiene and cyclohexene. These
are related in that under appropriate conditions that can all be reduced
to the same product, cyclohexane.
The DHh for "cyclohexatriene", a hypothetical molecule in which the double bonds are assumed to be isolated from each other, is calculated to be 3 times the value for cyclohexene. This value reflects the energy we could expect to be released from 3 isolated C=C. By comparing this value with the experimental value for benzene, we can conclude that benzene is 152 kJ or 36 kcal / mol more stable than the hypothetical system. This is the resonance energy for benzene. What is the resonance energy of 1,3-cyclohexadiene ? |
In principle, resonance energies can be calculated for any p systems. The following table contains data on a selection of systems, and some comments about them in relation to benzene or about their aromaticity. |
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