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

Detalhes bibliográficos
Autor(a) principal: Almeida, Patricia Saraiva Vilas Boas
Data de Publicação: 2022
Outros Autores: Maia, José Roberto da Silveira, Souza, Márcia Cristina de, Pacheco, Alison Geraldo
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Revista de Engenharia Química e Química
Texto Completo: https://periodicos.ufv.br/jcec/article/view/14608
Resumo: 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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spelling Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetateSíntese, Caracterização, Cálculos Teóricos de RMN e Estrutura Cristalina do 3-metil-1H-1,2,4?4-triazol-5-amina acetato1,2,4-Triazole compounds. Biological assay. Crystal structure. Spectroscopy.Compostos 1,2,4-Triazois. Testes biológicos. Estrutura cristalina. Espectroscopia.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.A reação de condensação entre bicarbonato de aminoguanidina com ácidos carboxílicos levou à formação de 3-metil-1S-1,2,4-triazol-5-amine (mta), 3-metil-1H-1,2,4?4-triazole-5-amine acetato (Hmta) e 3-fenil-1H-1,2,4-triazole-5-amine (pta). O composto N-(3-metil-1S-1,2,4-triazole-5-yl)propan-2-imine (mpta) foi obtido reagindo a mta com acetona, após uma tentativa de purificar mta neste solvente. O excesso de ácido acético obteve o Hmta durante a preparação do mta. Esses compostos foram caracterizados por espectroscopia infravermelha e multinuclear de NMR (1H e 13C), microanálise e ponto de fusão. Para investigar a formação de possíveis conformações tautoméricas de mta, pta e mpta em solução, utilizou-se uma abordagem teórica para calcular as mudanças químicas do carbono 13, com base nos valores do tensor de blindagem magnética (NMR) pelos métodos MPn e DFT. O ensaio biológico dos triazoles mta, pta e mpta contra Staphylococcus aureus, Bacillus subtilis, Escherichia coli e Salmonella typhimurium não mostrou atividade na maior concentração utilizada no experimento.Universidade Federal de Viçosa - UFV2022-09-21info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArtigo, Manuscrito, Eventosapplication/pdfhttps://periodicos.ufv.br/jcec/article/view/1460810.18540/jcecvl8iss7pp14608-01iThe Journal of Engineering and Exact Sciences; Vol. 8 No. 7 (2022); 14608-01iThe Journal of Engineering and Exact Sciences; Vol. 8 Núm. 7 (2022); 14608-01iThe Journal of Engineering and Exact Sciences; v. 8 n. 7 (2022); 14608-01i2527-1075reponame:Revista de Engenharia Química e Químicainstname:Universidade Federal de Viçosa (UFV)instacron:UFVenghttps://periodicos.ufv.br/jcec/article/view/14608/7481Copyright (c) 2022 The Journal of Engineering and Exact Scienceshttps://creativecommons.org/licenses/by/4.0info:eu-repo/semantics/openAccessAlmeida, Patricia Saraiva Vilas BoasMaia, José Roberto da SilveiraSouza, Márcia Cristina dePacheco, Alison Geraldo2022-10-24T12:05:38Zoai:ojs.periodicos.ufv.br:article/14608Revistahttp://www.seer.ufv.br/seer/rbeq2/index.php/req2/indexONGhttps://periodicos.ufv.br/jcec/oaijcec.journal@ufv.br||req2@ufv.br2446-94162446-9416opendoar:2022-10-24T12:05:38Revista de Engenharia Química e Química - Universidade Federal de Viçosa (UFV)false
dc.title.none.fl_str_mv Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate
Síntese, Caracterização, Cálculos Teóricos de RMN e Estrutura Cristalina do 3-metil-1H-1,2,4?4-triazol-5-amina acetato
title Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate
spellingShingle Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate
Almeida, Patricia Saraiva Vilas Boas
1,2,4-Triazole compounds. Biological assay. Crystal structure. Spectroscopy.
Compostos 1,2,4-Triazois. Testes biológicos. Estrutura cristalina. Espectroscopia.
title_short 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_sort Synthesis, Characterisation, Theoretical NMR Calculations and Crystal Structure of the 3-methyl-1H-1,2,4?4-triazole-5-amine acetate
author Almeida, Patricia Saraiva Vilas Boas
author_facet Almeida, Patricia Saraiva Vilas Boas
Maia, José Roberto da Silveira
Souza, Márcia Cristina de
Pacheco, Alison Geraldo
author_role author
author2 Maia, José Roberto da Silveira
Souza, Márcia Cristina de
Pacheco, Alison Geraldo
author2_role author
author
author
dc.contributor.author.fl_str_mv Almeida, Patricia Saraiva Vilas Boas
Maia, José Roberto da Silveira
Souza, Márcia Cristina de
Pacheco, Alison Geraldo
dc.subject.por.fl_str_mv 1,2,4-Triazole compounds. Biological assay. Crystal structure. Spectroscopy.
Compostos 1,2,4-Triazois. Testes biológicos. Estrutura cristalina. Espectroscopia.
topic 1,2,4-Triazole compounds. Biological assay. Crystal structure. Spectroscopy.
Compostos 1,2,4-Triazois. Testes biológicos. Estrutura cristalina. Espectroscopia.
description 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.
publishDate 2022
dc.date.none.fl_str_mv 2022-09-21
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Artigo, Manuscrito, Eventos
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv https://periodicos.ufv.br/jcec/article/view/14608
10.18540/jcecvl8iss7pp14608-01i
url https://periodicos.ufv.br/jcec/article/view/14608
identifier_str_mv 10.18540/jcecvl8iss7pp14608-01i
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv https://periodicos.ufv.br/jcec/article/view/14608/7481
dc.rights.driver.fl_str_mv Copyright (c) 2022 The Journal of Engineering and Exact Sciences
https://creativecommons.org/licenses/by/4.0
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Copyright (c) 2022 The Journal of Engineering and Exact Sciences
https://creativecommons.org/licenses/by/4.0
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Universidade Federal de Viçosa - UFV
publisher.none.fl_str_mv Universidade Federal de Viçosa - UFV
dc.source.none.fl_str_mv The Journal of Engineering and Exact Sciences; Vol. 8 No. 7 (2022); 14608-01i
The Journal of Engineering and Exact Sciences; Vol. 8 Núm. 7 (2022); 14608-01i
The Journal of Engineering and Exact Sciences; v. 8 n. 7 (2022); 14608-01i
2527-1075
reponame:Revista de Engenharia Química e Química
instname:Universidade Federal de Viçosa (UFV)
instacron:UFV
instname_str Universidade Federal de Viçosa (UFV)
instacron_str UFV
institution UFV
reponame_str Revista de Engenharia Química e Química
collection Revista de Engenharia Química e Química
repository.name.fl_str_mv Revista de Engenharia Química e Química - Universidade Federal de Viçosa (UFV)
repository.mail.fl_str_mv jcec.journal@ufv.br||req2@ufv.br
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