Abstract
The C-X and C-C bond dissociation energies of organic compounds can be explained in terms of the stabilization energies of these species and the corresponding radical (s). The lowest C-H bond strengths correspond to the so-called captodative radicals due to their relatively large stabilization energy. These species being most commonly transient, dehydrodimerization reactions are generally favoured by captodative substitution. On the other hand, the lowest C-C bond strengths correspond to species highly destabilized by steric strain or polar interactions. However, in many cases, the stabilization energy of the corresponding radicals plays also an important role in the thermal stability of substituted (cyclo)alkanes.
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