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Benzamidinium 2-meth­oxy­benzoate

The title mol­ecular salt, C(7)H(9)N(2) (+.)C(8)H(7)O(3) (−), was synthesized by reaction between benzamidine (benzene­carboximidamide) and 2-meth­oxy­benzoic acid. In the cation, the amidinium group has two similar C—N bonds [1.3070 (17) and 1.3145 (16) Å] and is almost coplanar with the benzene ri...

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Autor principal: Portalone, Gustavo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3770387/
https://www.ncbi.nlm.nih.gov/pubmed/24046672
http://dx.doi.org/10.1107/S1600536813016395
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author Portalone, Gustavo
author_facet Portalone, Gustavo
author_sort Portalone, Gustavo
collection PubMed
description The title mol­ecular salt, C(7)H(9)N(2) (+.)C(8)H(7)O(3) (−), was synthesized by reaction between benzamidine (benzene­carboximidamide) and 2-meth­oxy­benzoic acid. In the cation, the amidinium group has two similar C—N bonds [1.3070 (17) and 1.3145 (16) Å] and is almost coplanar with the benzene ring, making a dihedral angle of 5.34 (12)°. In the anion, the meth­oxy substituent forces the carboxyl­ate group to be twisted by 69.45 (6)° with respect to the plane of the aromatic fragment. In the crystal, the components are connected by two N(+)—H⋯O(−) (±)CAHB (charge-assisted hydrogen bonds), forming centrosymmetric ionic dimers with graph-set motif R (2) (2)(8). These ionic dimers are then joined in ribbons running along the b-axis direction by another R (4) (2)(8) motif involving the remaining N(+)—H⋯O(−) hydrogen bonds. Remarkably, at variance with the well known carb­oxy­lic dimer R (2) (2)(8) motif, the carboxyl­ate–amidinium pair is not planar, the dihedral angle between the planes defined by the CN(2) (+) and CO(2) (−) atoms being 18.57 (12)°.
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spelling pubmed-37703872013-09-17 Benzamidinium 2-meth­oxy­benzoate Portalone, Gustavo Acta Crystallogr Sect E Struct Rep Online Organic Papers The title mol­ecular salt, C(7)H(9)N(2) (+.)C(8)H(7)O(3) (−), was synthesized by reaction between benzamidine (benzene­carboximidamide) and 2-meth­oxy­benzoic acid. In the cation, the amidinium group has two similar C—N bonds [1.3070 (17) and 1.3145 (16) Å] and is almost coplanar with the benzene ring, making a dihedral angle of 5.34 (12)°. In the anion, the meth­oxy substituent forces the carboxyl­ate group to be twisted by 69.45 (6)° with respect to the plane of the aromatic fragment. In the crystal, the components are connected by two N(+)—H⋯O(−) (±)CAHB (charge-assisted hydrogen bonds), forming centrosymmetric ionic dimers with graph-set motif R (2) (2)(8). These ionic dimers are then joined in ribbons running along the b-axis direction by another R (4) (2)(8) motif involving the remaining N(+)—H⋯O(−) hydrogen bonds. Remarkably, at variance with the well known carb­oxy­lic dimer R (2) (2)(8) motif, the carboxyl­ate–amidinium pair is not planar, the dihedral angle between the planes defined by the CN(2) (+) and CO(2) (−) atoms being 18.57 (12)°. International Union of Crystallography 2013-06-19 /pmc/articles/PMC3770387/ /pubmed/24046672 http://dx.doi.org/10.1107/S1600536813016395 Text en © Gustavo Portalone 2013 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
Portalone, Gustavo
Benzamidinium 2-meth­oxy­benzoate
title Benzamidinium 2-meth­oxy­benzoate
title_full Benzamidinium 2-meth­oxy­benzoate
title_fullStr Benzamidinium 2-meth­oxy­benzoate
title_full_unstemmed Benzamidinium 2-meth­oxy­benzoate
title_short Benzamidinium 2-meth­oxy­benzoate
title_sort benzamidinium 2-meth­oxy­benzoate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3770387/
https://www.ncbi.nlm.nih.gov/pubmed/24046672
http://dx.doi.org/10.1107/S1600536813016395
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