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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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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2013
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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)°. |
format | Online Article Text |
id | pubmed-3770387 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT portalonegustavo benzamidinium2methoxybenzoate |