Synthesis and potentiometric titrations of some new 4-(benzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives in non-aqueous media

The synthesis of 3-alkyl(aryl)-4-[4-(dimethylamino)benzylideneamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (3) from the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2) with 4-(dimethylamino)benzaldehyde is described. The newly synthesized 3 type compounds were titrated potentiometrically with tetrabutylammonium hydroxide in three non-aqueous solvents, including acetonitrile, isopropyl alcohol and N,N-dimethylformamide. The half-neutralization potential values and the corresponding pK(a) values were determined for all cases. Thus, the effects of solvents and molecular structure upon acidity were investigated. In addition, N-acetyl derivatives of 3 type compounds were also obtained. The new synthesized compounds in the study were fully characterized.