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

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. (c) 2021 Elsevier B.V. All rights reserved.

Automated summary

The study explores the molecular design and synthetic strategies for triazole compounds by introducing a phenyl ring and a carboxymethyl sulfanyl moiety to facilitate protonation. The synthesized triazole compound was further characterized and studied in detail.