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The kinetics of nucleophilic displacement of chlorine from a series of 2-chloro-5-heteroaryl( or aryl)pyrimidines by piperidine have been studied in order to assess the electronic effects of the 5-substituent. The observed order of reactivity is 5-(1-methylpyrrol-2-yl) &lt; 5-p-anisyl &lt; 5-p-tolyl &lt; 5-phenyl &lt; 5-(2-thienyl) &lt; 5-(2-furyl) &lt; 5-(m-chlorophenyl). The reactions are enthalpy-controlled and the rate data can be explained as a consequence of the electron-withdrawing or electron-donating ability of the 5-substituent. Synthetic routes to the compounds studied are also described.

zeitschrift für naturforschung b

Electronic Effects of Aryl and Heteroaryl Groups on the Rate of Nucleophilic Displacement of Chlorine from 5-Heteroaryl(or Aryl)-2-chloropyrimidines by Piperidine