Abstract
Intramolecular acyl transfer was studied in eight aroyl derivatives of cis enols of acetylacetone using various semiempirical hamiltonians. The transition state geometry and activation energy for each derivative is reported. A reaction rate relative to that for the O-benzoyl derivative was calculated for each member in the series. The calculated relative rate constants were correlated to the substituent electronic constants, σ, and to experimental relative rate constants. Good correlations were obtained in both cases with the exceptions of the p-chloro and m-nitro aroyl groups. The rates of acyl transfer were enhanced by electron withdrawing aroyl groups. Calculations with the PM3 hamiltonians reproduced experimental trends better than using AM1.
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