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In this work, for the first time, an approach was suggested for determining the pKa of triazolo[5,1-c][1,2,4]triazine compounds in N,N-dimethylformamide using potentiometric titration. It was noted that change in system potential in the titration curves of triazolo[5,1-с][1,2,4]triazine are observed for compounds containing either H+ located at the nitrogen atom in position 1 or an –NH2 group. The calculated pKa values of the studied molecules correspond to the pKa values of moderately strong acids and are in the range of 2–8. The relationship was established between the acidity of the heterocyclic fragment and the presence of electron donor substituents. The obtained pKa values of the compounds correlate with the calculated possible deprotonation centers of the molecule. It was found that determining the acidity constants of substances is useful for clarifying the mechanisms of their transformations. The possibility of establishing a relationship between the structure of the compound, pKa, and probable biological activity was shown.