Transmission of polar effects: quantitative reversal of substituent dipolar effect
Abstract
A study of the pKa values of 1-(8-substituted naphthyl) propiolic acids has been made and a reversal of the normal substituent effect of the helogeno-substituents has been observed; this result is an almost quantitative reversal of the effects observed in a suitable model, the 3-substituted propiolic acids, thus confirming transmission by an electrostatic field effect.