An alternative approach to the problem of assessing destabilization energies (strain energies) in cyclic hydrocarbons

Reaction involving no hypothetical structures having averaged group energies or particular bond energy assignments are described, that provide an alternative basis for evaluating strain energies of cyclic hydrocarbons. These reactions match CC bonds in the sense of having equal number of sp³-sp³, sp³-sp², sp²-sp², etc. bonds in reactants and products, while simultaneously matching various CH bonds as closely as possible. Such reactions single out those structural features that lead to destabilizations of strained ring systems. Theoretical and experimental molecular indices are introduced as a measure of these destabilizing effects, and are compared ring strain energies.