Abstract
The acid dissociation constants of a number of diphenyl- and phenylpyridylamines bearing multiple electron-withdrawing substituents were measured in 1:1 ethanol/water. The ionization constants were correlated quantitatively by application of Hammett-Taft-type equations and regression analysis. The effets that were exerted by substituents that were crowded near each other in the vicinity of the NH bridge of these compounds could be readily separated into electronic and steric components. The effects included those that were specific to the proximity of the substituent to the NH bridge and those that influenced the behavior of the aza functional group of the pyridinyl compounds electronically
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