Second-order rate constants ($k_N$) have been measured spectrophotometrically for the reactions of benzyl 2-pyridyl carbonate $mathbf{7}$ and $t$-butyl 2-pyridyl carbonate $mathbf{8}$ with a series of alicyclic secondary amines in $H_2O$ at $25.0^{circ}C$. Substrate $mathbf{8}$ is less reactive than $mathbf{7}$. Steric hindrance exerted by the bulky $t$-Bu group of $mathbf{8}$ has been suggested to be responsible for the decreased reactivity. The Br${o}$nsted-type plots for the reactions of $mathbf{7}$ and $mathbf{8}$ are linear with ${eta}_{nuc}=0.49$ and 0.44, respectively, which is typical for reactions reported previously to proceed through a concerted mechanism. Aminolyses of $mathbf{7}$ and $mathbf{8}$ were expected to proceed through a zwitterionic tetrahedral intermediate $T^{pm}$, which would be stabilized through an intramolecular H-bonding interaction. However, the kinetic results suggest that the reactions proceed through a concerted mechanism. The H-bonding interaction in $T^{pm}$ has been suggested to accelerate the rate of leaving-group expulsion from $T^{pm}$. Another factor that might accelerate expulsion of the leaving group is the "push" provided by the RO group in $T^{pm}$ through resonance interactions. Thus, it has been concluded that the enhanced nucleofugality through the H-bonding interaction and the "push" provided by the RO group forces the reactions to proceed through a concerted mechanism.