Theoretical study of the effect of water in the process of proton transfer of glycinamide

For the purpose of investigating the tautomerism from glycinamide (G) to glycinamidic acid (G*) induced by proton transfer, we carried out a study of structural interconversion of the two tautomers and the relative stabilizing influences of water during the tautomerization process. Throughout the study, we used density functional theory (DFT) calculations at the B3LYP/6-311++G** level of theory, also considering the correction functions, that is, the effect of basis set superposition error (BSSE). Totally, 42 geometries, including fourteen important transition states, were optimized, and their geometric parameters have also been discussed in detail. Water molecules were gradually put in three different regions in the vicinity of G and its tautomer G*. The calculation results indicate that water in two of these regions can protect G from tautomerizing to G*, while in another region, water can assist in the tautomerism; this reveals that water molecules have stabilization and mutagenicity effects for G simultaneously.