3-Carb­oxy-5-(pyridinium-4-yl)benzoate: a redetermination

The title compound, C(13)H(9)NO(4), crystallizes in a zwitterionic form with the pyridine N atom protonated and the carboxyl OH group deprotonated. The benzene and pyridinium rings are inclined with a dihedral angle of 31.42 (14)° between them. A previous report of this stucture claims, we believe i...

Descripción completa

Detalles Bibliográficos
Autores principales: Li, Shi-Jie, Miao, Dong-Liang, Song, Wen-Dong, Tong, Shao-Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3120316/
https://www.ncbi.nlm.nih.gov/pubmed/21754747
http://dx.doi.org/10.1107/S1600536811016394
_version_ 1782206651651063808
author Li, Shi-Jie
Miao, Dong-Liang
Song, Wen-Dong
Tong, Shao-Wei
author_facet Li, Shi-Jie
Miao, Dong-Liang
Song, Wen-Dong
Tong, Shao-Wei
author_sort Li, Shi-Jie
collection PubMed
description The title compound, C(13)H(9)NO(4), crystallizes in a zwitterionic form with the pyridine N atom protonated and the carboxyl OH group deprotonated. The benzene and pyridinium rings are inclined with a dihedral angle of 31.42 (14)° between them. A previous report of this stucture claims, we believe incorrectly, that neither of the carboxyl­ate groups is deprotonated [Zhang et al. (2010 ▶). Acta Cryst. E66, o2928–o2928]. In the crystal, inter­molecular O—H⋯O, N—H⋯O and weak C—H⋯O hydrogen-bonding inter­actions link adjacent mol­ecules into a three-dimensional supra­molecular network.
format Online
Article
Text
id pubmed-3120316
institution National Center for Biotechnology Information
language English
publishDate 2011
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-31203162011-07-13 3-Carb­oxy-5-(pyridinium-4-yl)benzoate: a redetermination Li, Shi-Jie Miao, Dong-Liang Song, Wen-Dong Tong, Shao-Wei Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(13)H(9)NO(4), crystallizes in a zwitterionic form with the pyridine N atom protonated and the carboxyl OH group deprotonated. The benzene and pyridinium rings are inclined with a dihedral angle of 31.42 (14)° between them. A previous report of this stucture claims, we believe incorrectly, that neither of the carboxyl­ate groups is deprotonated [Zhang et al. (2010 ▶). Acta Cryst. E66, o2928–o2928]. In the crystal, inter­molecular O—H⋯O, N—H⋯O and weak C—H⋯O hydrogen-bonding inter­actions link adjacent mol­ecules into a three-dimensional supra­molecular network. International Union of Crystallography 2011-05-07 /pmc/articles/PMC3120316/ /pubmed/21754747 http://dx.doi.org/10.1107/S1600536811016394 Text en © Li et al. 2011 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
Li, Shi-Jie
Miao, Dong-Liang
Song, Wen-Dong
Tong, Shao-Wei
3-Carb­oxy-5-(pyridinium-4-yl)benzoate: a redetermination
title 3-Carb­oxy-5-(pyridinium-4-yl)benzoate: a redetermination
title_full 3-Carb­oxy-5-(pyridinium-4-yl)benzoate: a redetermination
title_fullStr 3-Carb­oxy-5-(pyridinium-4-yl)benzoate: a redetermination
title_full_unstemmed 3-Carb­oxy-5-(pyridinium-4-yl)benzoate: a redetermination
title_short 3-Carb­oxy-5-(pyridinium-4-yl)benzoate: a redetermination
title_sort 3-carb­oxy-5-(pyridinium-4-yl)benzoate: a redetermination
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3120316/
https://www.ncbi.nlm.nih.gov/pubmed/21754747
http://dx.doi.org/10.1107/S1600536811016394
work_keys_str_mv AT lishijie 3carboxy5pyridinium4ylbenzoatearedetermination
AT miaodongliang 3carboxy5pyridinium4ylbenzoatearedetermination
AT songwendong 3carboxy5pyridinium4ylbenzoatearedetermination
AT tongshaowei 3carboxy5pyridinium4ylbenzoatearedetermination

Ejemplares similares