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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

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Abstract
Both the 3-amino-2H,4H-1,2,4-triazolium cation and the pyrazine-2-carboxylate anion in the title salt, C2H5N4+center dot C5H3N2O2-, 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 angstrom) and the carboxylate group in the anion is 3.7 (3)degrees. 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 center dot center dot center dot 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 pi-pi stacking interactions between the triazole and pyrazine rings.
Keywords
ionothermal synthesis, decarboxylation, crystal structure, triazolium salt, hydrogen bonding, pi-pi stacking interactions, MOLECULAR CO-CRYSTALS, CARBOXYLIC-ACIDS, IONIC LIQUIDS, 3-AMINO-1, 2, 4-TRIAZOLE, COCRYSTALS, ADDUCTS, 3-AMINO-1H-1, 2, 4-TRIAZOLE, 2-AMINOPYRIMIDINE, 3-HYDROXYPYRIDINE

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Citation

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MLA
Fernandes, José A., et al. “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.” ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol. 71, no. 7, 2015, pp. 840–43, doi:10.1107/S205698901501172X.
APA
Fernandes, J. A., Liu, B., Tomé, J., Cunha-Silva, L., & Almeida Paz, F. A. (2015). 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. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 71(7), 840–843. https://doi.org/10.1107/S205698901501172X
Chicago author-date
Fernandes, José A, Bing Liu, João Tomé, Luís Cunha-Silva, and Filipe A Almeida Paz. 2015. “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.” ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS 71 (7): 840–43. https://doi.org/10.1107/S205698901501172X.
Chicago author-date (all authors)
Fernandes, José A, Bing Liu, João Tomé, Luís Cunha-Silva, and Filipe A Almeida Paz. 2015. “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.” ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS 71 (7): 840–843. doi:10.1107/S205698901501172X.
Vancouver
1.
Fernandes JA, Liu B, Tomé J, Cunha-Silva L, Almeida Paz FA. 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. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS. 2015;71(7):840–3.
IEEE
[1]
J. A. Fernandes, B. Liu, J. Tomé, L. Cunha-Silva, and F. A. Almeida Paz, “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,” ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol. 71, no. 7, pp. 840–843, 2015.
@article{7139884,
  abstract     = {{Both the 3-amino-2H,4H-1,2,4-triazolium cation and the pyrazine-2-carboxylate anion in the title salt, C2H5N4+center dot C5H3N2O2-, 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 angstrom) and the carboxylate group in the anion is 3.7 (3)degrees. 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 center dot center dot center dot 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 pi-pi stacking interactions between the triazole and pyrazine rings.}},
  author       = {{Fernandes, José A and Liu, Bing and Tomé, João and Cunha-Silva, Luís and Almeida Paz, Filipe A}},
  issn         = {{2056-9890}},
  journal      = {{ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS}},
  keywords     = {{ionothermal synthesis,decarboxylation,crystal structure,triazolium salt,hydrogen bonding,pi-pi stacking interactions,MOLECULAR CO-CRYSTALS,CARBOXYLIC-ACIDS,IONIC LIQUIDS,3-AMINO-1,2,4-TRIAZOLE,COCRYSTALS,ADDUCTS,3-AMINO-1H-1,2,4-TRIAZOLE,2-AMINOPYRIMIDINE,3-HYDROXYPYRIDINE}},
  language     = {{eng}},
  number       = {{7}},
  pages        = {{840--843}},
  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}},
  url          = {{http://doi.org/10.1107/S205698901501172X}},
  volume       = {{71}},
  year         = {{2015}},
}

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