6‑mercaptopurine belongs to a family of heterocycles that are subject to actual research in several fields. A density functional theory study was carried out to advance in the understanding of 6‑mercaptopurine physicochemical properties. A full geometry optimization was performed for all the possible tautomers in gas phase. Several molecular and electronic structure properties for the more favored tautomers were calculated. Also, a thermodynamic stability study of the heterocyclic protonic transfer processes and tautomerism were carried out. Finally, the theoretical IR vibrational spectra and their characterization were obtained for the more favored forms. From the study, several theoretical characteristics were found, which have been employed to predict and account for some features of the experimental 6‑mercaptopurine physicochemical and chemical behavior.
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