Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate
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)prop...
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Universidade Federal de Viçosa (UFV)
2022-09-01
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| Series: | The Journal of Engineering and Exact Sciences |
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| Online Access: | https://periodicos.ufv.br/jcec/article/view/14608 |
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| author | Patricia Saraiva Vilas Boas Almeida José Roberto da Silveira Maia Márcia Cristina de Souza Alison Geraldo Pacheco |
| author_facet | Patricia Saraiva Vilas Boas Almeida José Roberto da Silveira Maia Márcia Cristina de Souza Alison Geraldo Pacheco |
| author_sort | Patricia Saraiva Vilas Boas Almeida |
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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.
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| format | Article |
| id | doaj-art-ee1ba029f4304324bdff9b5c8efd5dd2 |
| institution | Kabale University |
| issn | 2527-1075 |
| language | English |
| publishDate | 2022-09-01 |
| publisher | Universidade Federal de Viçosa (UFV) |
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| series | The Journal of Engineering and Exact Sciences |
| spelling | doaj-art-ee1ba029f4304324bdff9b5c8efd5dd22025-02-02T19:56:08ZengUniversidade Federal de Viçosa (UFV)The Journal of Engineering and Exact Sciences2527-10752022-09-018710.18540/jcecvl8iss7pp14608-01iSynthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetatePatricia Saraiva Vilas Boas Almeida0José Roberto da Silveira Maia1Márcia Cristina de Souza2Alison Geraldo Pacheco3Departamento de Química, Universidade Federal de Viçosa, BrazilDepartamento de Química, Universidade Federal de Viçosa, BrazilDepartamento de Química, Universidade Federal de Juiz de Fora, BrazilInstituto Federal de Educação, IFSULDEMINAS, Brazil 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. https://periodicos.ufv.br/jcec/article/view/146081,2,4-Triazole compounds. Biological assay. Crystal structure. Spectroscopy. |
| spellingShingle | Patricia Saraiva Vilas Boas Almeida José Roberto da Silveira Maia Márcia Cristina de Souza Alison Geraldo Pacheco Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate The Journal of Engineering and Exact Sciences 1,2,4-Triazole compounds. Biological assay. Crystal structure. Spectroscopy. |
| title | Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate |
| title_full | Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate |
| title_fullStr | Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate |
| title_full_unstemmed | Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate |
| title_short | Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate |
| title_sort | synthesis characterisation theoretical nmr calculations and crystal structure of the 3 methyl 1h 1 2 4 4 triazole 5 amine acetate |
| topic | 1,2,4-Triazole compounds. Biological assay. Crystal structure. Spectroscopy. |
| url | https://periodicos.ufv.br/jcec/article/view/14608 |
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