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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...

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Detalles Bibliográficos
Autores principales: Ton, Quoc-Cuong, Bolte, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
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.
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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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