Add time:07/17/2019         Source:sciencedirect.com

In the present paper, twelve Schiff bases derived from 3-amino-1H-1,2,4-triazole (ATz) and various benzaldehydes, and salicylaldehydes were synthesized. The 1H, 13C, and 15N NMR data are discussed in relation to the structure of ATz and its imine products. In addition, X-ray, ATR-FTIR, and UV–Vis analytical techniques are used for structure elucidation of ATz-based Schiff bases. It was found that the starting material, 3-amino-1H-1,2,4-triazole, exists as tautomeric mixture of three forms (Graphical ) in solution, whereas in the solid state (13C and 15N CPMAS data) potentially tautomeric proton is located on nitrogen atom traditionally marked as N-2 (Graphical , 2NH structure). All investigated Schiff bases derived from salicylaldehydes exist in both phases as tautomeric equilibrium mixtures, where enol-imine forms are dominated structures. The positions of those equilibria only very slightly depend on substituents in phenol ring. Generally, the contributions of keto-amine forms in the solid state are higher comparing with DMSO solutions.

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