Rate constants for the reaction of ethyl bromoacetate with three series of substituted naphthoate ions have been measured in an acetone-water mixture (90% v/v). Using σp values rate constants at 30o correlate well with the Hammett equation yielding ρ=−0.54, −0.19 and −0.25 for (4,1−), (6,1−) and (6,2−) series, respectively. Comparison of these ρ values with those of the reaction of phenacyl bromide reveals the failure of the reactivity-selectivity principle RSP in these reactions. Failure of RSP has been explained in terms of isoselective temperature.
Volume 135, 2023
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