On the protonation of a polysubstituted 1,2,4-triazole: A structural study of a hexabromotellurate salt

Abstract

Previous findings in the chemistry of 5-amino-1,2,4-triazol-3-thioles show the possibility of protonation of such systems on the nitrogen atom in position 1 of the triazole ring. To expand the molecular design synthetic strategies for triazole systems, it was suggested that the weakening of the basicity of the guanidine fragment via the introduction of a phenyl ring from one side and addition of a flexible 3-(carboxymethyl)sulfanyl moiety in position 3 of the cycle can lead to the formation of a triazole compound that would attach a proton on the nitrogen atom in the second position of the ring. Synthesis of the model 3-[(carboxymethyl)sulfanyl]-4-phenyl-5-phenylamino-4H-1,2,4-triazole via the selective S-alkylation of known 4-phenyl-5-phenylamino-1,2,4-triazole-3-thione has been performed. The synthesized triazole amino acid was converted into a corresponding hexabromotellurate salt which has been further explored and characterized via DFT, NMR and XRD methods.