Abstract
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 σ p 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.
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Rajasekaran, K., Gnanasekaran, C. Reaction of ethyl bromoacetate with substituted naphthoate ions. Proc. Indian Acad. Sci. (Chem. Sci.) 97, 47–53 (1986). https://doi.org/10.1007/BF02880841
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DOI: https://doi.org/10.1007/BF02880841