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Intra- and intermolecular proton transfer in 2,6-diaminopyridinium 4-hydroxypyridin-1-ium-2,6-dicarboxylate
Chelidamic acid (4-hydroxypyridine-2,6-dicarboxylic acid) and 2,6-diaminopyridine react to form the title salt, C(5)H(8)N(3) (+)·C(7)H(4)NO(5) (−); there are two formula units in the asymmetric unit. The pyridine N atom of 2,6-diaminopyridine is protonated whereas chelidamic acid is deprotonat...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2012
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3470218/ https://www.ncbi.nlm.nih.gov/pubmed/23125662 http://dx.doi.org/10.1107/S1600536812037580 |
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author | Ton, Quoc-Cuong Bolte, Michael |
author_facet | Ton, Quoc-Cuong Bolte, Michael |
author_sort | Ton, Quoc-Cuong |
collection | PubMed |
description | Chelidamic acid (4-hydroxypyridine-2,6-dicarboxylic acid) and 2,6-diaminopyridine react to form the title salt, C(5)H(8)N(3) (+)·C(7)H(4)NO(5) (−); there are two formula units in the asymmetric unit. The pyridine N atom of 2,6-diaminopyridine is protonated whereas chelidamic acid is deprotonated at both carboxylate groups but protonated at the N atom; the reaction involves intra- and intermolecular proton transfer. In the crystal, each 2,6-diaminopyridinium cation participates in five strong N—H⋯O hydrogen bonds (including one bifurcated hydrogen bond). The crystal structure also features strong O—H⋯O hydrogen bonds between the chelidamate anions, leading to chains along the a axis. |
format | Online Article Text |
id | pubmed-3470218 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-34702182012-11-02 Intra- and intermolecular proton transfer in 2,6-diaminopyridinium 4-hydroxypyridin-1-ium-2,6-dicarboxylate Ton, Quoc-Cuong Bolte, Michael Acta Crystallogr Sect E Struct Rep Online Organic Papers Chelidamic acid (4-hydroxypyridine-2,6-dicarboxylic acid) and 2,6-diaminopyridine react to form the title salt, C(5)H(8)N(3) (+)·C(7)H(4)NO(5) (−); there are two formula units in the asymmetric unit. The pyridine N atom of 2,6-diaminopyridine is protonated whereas chelidamic acid is deprotonated at both carboxylate groups but protonated at the N atom; the reaction involves intra- and intermolecular proton transfer. In the crystal, each 2,6-diaminopyridinium cation participates in five strong N—H⋯O hydrogen bonds (including one bifurcated hydrogen bond). The crystal structure also features strong O—H⋯O hydrogen bonds between the chelidamate anions, leading to chains along the a axis. International Union of Crystallography 2012-09-05 /pmc/articles/PMC3470218/ /pubmed/23125662 http://dx.doi.org/10.1107/S1600536812037580 Text en © Ton and Bolte 2012 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 | Organic Papers Ton, Quoc-Cuong Bolte, Michael Intra- and intermolecular proton transfer in 2,6-diaminopyridinium 4-hydroxypyridin-1-ium-2,6-dicarboxylate |
title | Intra- and intermolecular proton transfer in 2,6-diaminopyridinium 4-hydroxypyridin-1-ium-2,6-dicarboxylate |
title_full | Intra- and intermolecular proton transfer in 2,6-diaminopyridinium 4-hydroxypyridin-1-ium-2,6-dicarboxylate |
title_fullStr | Intra- and intermolecular proton transfer in 2,6-diaminopyridinium 4-hydroxypyridin-1-ium-2,6-dicarboxylate |
title_full_unstemmed | Intra- and intermolecular proton transfer in 2,6-diaminopyridinium 4-hydroxypyridin-1-ium-2,6-dicarboxylate |
title_short | Intra- and intermolecular proton transfer in 2,6-diaminopyridinium 4-hydroxypyridin-1-ium-2,6-dicarboxylate |
title_sort | intra- and intermolecular proton transfer in 2,6-diaminopyridinium 4-hydroxypyridin-1-ium-2,6-dicarboxylate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3470218/ https://www.ncbi.nlm.nih.gov/pubmed/23125662 http://dx.doi.org/10.1107/S1600536812037580 |
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