Accurate estimates of reaction thermochemistry can be obtained using group additivity methods.  Although these methods are useful for predicting energetics, they provide limited insight into the factors that influence molecular stability. Several bond additivity methods have been recently proposed by us and others that may overcome this limitation. We have proposed the vicinal interactions (VI) model in which the heat of formation for an organic molecule is represented by a combination of bond energies and vicinal bond interactions.  Theoretical support for this model stems from ab initio electronic structure calculations that reveal the essential role of steric bond-bond and delocalizing bond-antibond interactions in unstrained organic molecules. We have demonstrated that the VI model can be used to accurately predict heats of formation for hydrocarbons and to interpret the origin of the differing stabilities of hydrocarbon isomers and conformers.  We discuss the VI model and its extension to amines in this presentation.

Vicinal interactions model: Predicting and interpreting the stability of amines

239th National Meeting (2010)

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