Abstract
Literature data for nucleophilic addition at C-4 of C-3 substituted 1-methylpyridinium cations are evaluated. It is shown that sufficient data are available to allow the confident evaluation of a linear free energy relationship for the equilibration of these cations with their C-4 hydroxide adducts (pseudobases) in aqueous solution: pK R+ = -8.5 (±0.4) σ-p + 20.5 (± 0.5) This allows the prediction of pKR+ = 20.5 for pseudobase formation at C-4 of the 1-methylpyridinium cation. A less confident estimate of pK R+ = 18.2 at C-2 of this cation is also made.
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