Quantum chemical studies on tautomerism and basicity behavior of some 1,2,4-triazole derivatives

Authors : Cemil ÖĞRETİR, Yadigar GÜLSEVEN SIDIR, İsa SIDIR and Erol TAŞAL

Pages : 977-990

Doi:10.3906/vet-1110-46

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Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :The acidity constants, relative stabilities, and tautomeric equilibrium constants of some 1,2,4-triazole derivatives were determined using the density functional theory insert ignore into journalissuearticles values(DFT); with the B3LYP method and 6-311Ginsert ignore into journalissuearticles values(d,p); basis set. The integral equation formalism version of the polarizable continuum model insert ignore into journalissuearticles values(IEFPCM); was used in the calculations of the aqueous phase. The calculated tautomeric equilibrium and relative stabilities values revealed that the 4H-1,2,4 triazole form for all studied molecules was favored over the 1H-1,2,4 triazole form. Protonation processes indicated the predominance of the 1H-1,2,4 triazole form over the 2H-1,2,4 triazole form. The correlation attempt between the experimental and the calculated acidity constants, pKa values, revealed that they are quite close to the experimental values and they correlate well with a regression of around unity insert ignore into journalissuearticles values(R2 = 1);.
Keywords : 1, 2, 4 Triazole, proton affinity, tautomerism, acidity constant, nucleophilicity