Abstract
A set of 22 alkylated or halogenated phenols was subjected to a comparative analysis of the solution acidity as expressed by p K a, the respective σ Hammett substituent constants and the gas-phase acidity. Quantum chemical calculations within the PM3 model lead to the anion ionization potential as an intrinsic acidity scale for the phenols, the latter of which reveals differences between the gas-phase and solution acidity and the related Hammett constants with respect to their dependence on the electronic structure of the compounds. In particular, the use of para constants for ortho substituents is critically analysed using both the solution and the intrinsic acidity as independent points of reference.
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