Abstract
A novel scale of Lewis acidities earlier proposed (Laszlo. P.; Teston, M.; J. Am. Chem. Soc, 1990, 112, 8750-8754) is based on the calculated (MNDO) energy of the π* level in the 1:1 complex formed between the Lewis acid and crotonaldehyde. We show here that this measure of Lewis acidity has also predictive value. It accounts very nicely for the rates of the ene reaction between β-pinene and methyl acrylate. The attendant free energy relationship between the Gibbs free energy change ΔG* for this reaction and the calculated π* MO energy change is linear with a correlation coefficient of 0.99 for six points. This observation provides a new mechanistic test for the influence of a Lewis acidic catalyst on a chemical reaction.
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