The behaviors of double proton transfer (DPT) between two model peptide compounds, that is, glycinamide and formamide, have been investigated employing the B3LYP/6-311++G** level of theory. Thermodynamic and especially kinetic parameters, such as tautomeric energy, equilibrium constant, and barrier heights, have been discussed. The relevant quantities involved in the DPT process, such as geometrical changes, interaction energies, and the intrinsic reaction coordinate (IRC) calculations, have also been studied. Contrary to those tautomeric processes directly assisted with one, two, and three water molecules, the participation of a formamide molecule disfavors the tautomeric process for both glycinamide and formamide thermodynamically compared with their direct tautomeric cases. The DPT process proceeds with a concerted mechanism rather than a stepwise one since no ion-pair complexes have been located during the PT process. The barrier heights are 20.45 and 0.70 kcal/mol for the forward and reverse directions, respectively. However, both of them have been reduced by 3.47 and 3.07 kcal/mol to 16.98 and -2.37 kcal/mol with further inclusion of zero-point vibrational energy (ZPVE) corrections, which has been further reproduced by the full optimizations at the MP2(FULL)/6-311++G** level of theory. Additionally, the solvent effects on the thermodynamic and kinetic processes have been predicted qualitatively employing the IPCM model within the framework of the self-consistent reaction field (SCRF) theory. More importantly, the reliability of the B3LYP/6-311++G** level of theory in exploring the DPT phenomena in the glycinamide complexes has been confirmed for future study.