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.
K. Bowden and M. Hojatti, J. Chem. Soc., Chem. Commun., 1982, 273 DOI: 10.1039/C39820000273
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