Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate

Patricia Saraiva Vilas Boas Almeida; José Roberto da Silveira Maia; Márcia Cristina de Souza; Alison Geraldo Pacheco

doi:10.18540/jcecvl8iss7pp14608-01i

Auteurs

Patricia Saraiva Vilas Boas Almeida Departamento de Química, Universidade Federal de Viçosa, Brazil
José Roberto da Silveira Maia Departamento de Química, Universidade Federal de Viçosa, Brazil https://orcid.org/0000-0001-5715-8763
Márcia Cristina de Souza Departamento de Química, Universidade Federal de Juiz de Fora, Brazil https://orcid.org/0000-0001-8333-3617
Alison Geraldo Pacheco Instituto Federal de Educação, IFSULDEMINAS, Brazil https://orcid.org/0000-0003-1338-0340

DOI :

https://doi.org/10.18540/jcecvl8iss7pp14608-01i

Mots-clés :

1,2,4-Triazole compounds. Biological assay. Crystal structure. Spectroscopy.

Résumé

The condensation reaction between aminoguanidine bicarbonate with carboxylic acids led to the formation of 3-methyl-1H-1,2,4-triazole-5-amine (mta), 3-methyl-1H-1,2,4l⁴-triazole-5-amine acetate (Hmta) and 3-phenyl-1H-1,2,4-triazole-5-amine (pta). The compound N-(3-methyl-1H-1,2,4-triazole-5-yl)propan-2-imine (mpta) was obtained by reacting the mta with acetone, upon an attempt of purifying mta in this solvent. The excess of acetic acid obtained the Hmta during the preparation of mta. These compounds were characterised by infrared and multinuclear NMR (¹H and ¹³C) spectroscopy, microanalysis, and melting point. To investigate the formation of possible tautomeric conformations of mta, pta and mpta in solution, a theoretical approach was used to calculate the chemical shifts of carbon 13, based on the values of magnetic shielding tensor (NMR) by MPn and DFT methods. The biological assay of the triazoles mta, pta and mpta against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Salmonella typhimurium showed no activity at the highest concentration used in the experiment.