Intramolecular hydrolyses of amides and anilides were examined over wide pH ranges at 90° Shape of pH-rate plofiles indicates that the relative reactivity of ionized (k'RO-) and un-ionized (k'ROH) alcohol functions toward amide linkage is governed by difference in pKa between attacking group alcohol and leaving group amine. As predicted from the theoretical consideration, their rate constants, k'RO- and k'ROH, were found to have good linear free-energy correlation.
