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Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxylate: an unexpected salt arising from the decarboxylation of both precursors
Both the 3-amino-2H,4H-1,2,4-triazolium cation and the pyrazine-2-carboxylate anion in the title salt, C(2)H(5)N(4) (+)·C(5)H(3)N(2)O(2) (−), were formed by an unexpected decarboxylation reaction, from 5-amino-1H-1,2,4-triazole-3-carboxylic acid and pyrazine-2,3-dicarboxylic acid, respectivel...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4518908/ https://www.ncbi.nlm.nih.gov/pubmed/26279881 http://dx.doi.org/10.1107/S205698901501172X |
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author | Fernandes, José A. Liu, Bing Tomé, João P. C. Cunha-Silva, Luís Almeida Paz, Filipe A. |
author_facet | Fernandes, José A. Liu, Bing Tomé, João P. C. Cunha-Silva, Luís Almeida Paz, Filipe A. |
author_sort | Fernandes, José A. |
collection | PubMed |
description | Both the 3-amino-2H,4H-1,2,4-triazolium cation and the pyrazine-2-carboxylate anion in the title salt, C(2)H(5)N(4) (+)·C(5)H(3)N(2)O(2) (−), were formed by an unexpected decarboxylation reaction, from 5-amino-1H-1,2,4-triazole-3-carboxylic acid and pyrazine-2,3-dicarboxylic acid, respectively. The dihedral angle between the pyrazine ring (r.m.s. deviation = 0.008 Å) and the carboxylate group in the anion is 3.7 (3)°. The extended structure of the salt contains a supramolecular zigzag tape in which cations and anions are engaged in strong and highly directional N—H⋯N,O hydrogen bonds, forming R (2) (2)(8) and R (2) (2)(9) graph-set motifs. The packing between the tapes is mediated by π–π stacking interactions between the triazole and pyrazine rings. |
format | Online Article Text |
id | pubmed-4518908 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-45189082015-08-14 Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxylate: an unexpected salt arising from the decarboxylation of both precursors Fernandes, José A. Liu, Bing Tomé, João P. C. Cunha-Silva, Luís Almeida Paz, Filipe A. Acta Crystallogr E Crystallogr Commun Research Communications Both the 3-amino-2H,4H-1,2,4-triazolium cation and the pyrazine-2-carboxylate anion in the title salt, C(2)H(5)N(4) (+)·C(5)H(3)N(2)O(2) (−), were formed by an unexpected decarboxylation reaction, from 5-amino-1H-1,2,4-triazole-3-carboxylic acid and pyrazine-2,3-dicarboxylic acid, respectively. The dihedral angle between the pyrazine ring (r.m.s. deviation = 0.008 Å) and the carboxylate group in the anion is 3.7 (3)°. The extended structure of the salt contains a supramolecular zigzag tape in which cations and anions are engaged in strong and highly directional N—H⋯N,O hydrogen bonds, forming R (2) (2)(8) and R (2) (2)(9) graph-set motifs. The packing between the tapes is mediated by π–π stacking interactions between the triazole and pyrazine rings. International Union of Crystallography 2015-06-24 /pmc/articles/PMC4518908/ /pubmed/26279881 http://dx.doi.org/10.1107/S205698901501172X Text en © Fernandes et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Research Communications Fernandes, José A. Liu, Bing Tomé, João P. C. Cunha-Silva, Luís Almeida Paz, Filipe A. Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxylate: an unexpected salt arising from the decarboxylation of both precursors |
title | Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxylate: an unexpected salt arising from the decarboxylation of both precursors |
title_full | Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxylate: an unexpected salt arising from the decarboxylation of both precursors |
title_fullStr | Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxylate: an unexpected salt arising from the decarboxylation of both precursors |
title_full_unstemmed | Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxylate: an unexpected salt arising from the decarboxylation of both precursors |
title_short | Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxylate: an unexpected salt arising from the decarboxylation of both precursors |
title_sort | crystal structure of 5-amino-4h-1,2,4-triazol-1-ium pyrazine-2-carboxylate: an unexpected salt arising from the decarboxylation of both precursors |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4518908/ https://www.ncbi.nlm.nih.gov/pubmed/26279881 http://dx.doi.org/10.1107/S205698901501172X |
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