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4-(Dimethylamino)pyridinium 4-toluenesulfonate
In the title compound, C(7)H(11)N(2) (+)·C(7)H(7)O(3)S(−), the cation is protonated at the N atom of the heterocyclic ring. The dimethylamino group lies close to the pyridinium ring plane with a dihedral angle between the pyridinium and the dimethylamine CNC planes of 3.82 (17)°. The N—C bond link...
Autores principales: | , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2008
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960775/ https://www.ncbi.nlm.nih.gov/pubmed/21201959 http://dx.doi.org/10.1107/S1600536808004856 |
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author | McAdam, C. John Simpson, Jim |
author_facet | McAdam, C. John Simpson, Jim |
author_sort | McAdam, C. John |
collection | PubMed |
description | In the title compound, C(7)H(11)N(2) (+)·C(7)H(7)O(3)S(−), the cation is protonated at the N atom of the heterocyclic ring. The dimethylamino group lies close to the pyridinium ring plane with a dihedral angle between the pyridinium and the dimethylamine CNC planes of 3.82 (17)°. The N—C bond linking the dimethylamino substituent to the pyridinium ring is characteristically short [1.3360 (19) Å], suggesting some delocalization in the cation. In the crystal structure, N—H⋯O hydrogen bonds link individual pairs of cations and anions. The structure is further stabilized by an extensive series of C—H⋯O hydrogen bonds, augmented by π–π [centroid–centroid distance between adjacent pyridinium rings = 3.5807 (10) Å] and C—H⋯π interactions, giving a network structure. |
format | Text |
id | pubmed-2960775 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29607752010-12-30 4-(Dimethylamino)pyridinium 4-toluenesulfonate McAdam, C. John Simpson, Jim Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(7)H(11)N(2) (+)·C(7)H(7)O(3)S(−), the cation is protonated at the N atom of the heterocyclic ring. The dimethylamino group lies close to the pyridinium ring plane with a dihedral angle between the pyridinium and the dimethylamine CNC planes of 3.82 (17)°. The N—C bond linking the dimethylamino substituent to the pyridinium ring is characteristically short [1.3360 (19) Å], suggesting some delocalization in the cation. In the crystal structure, N—H⋯O hydrogen bonds link individual pairs of cations and anions. The structure is further stabilized by an extensive series of C—H⋯O hydrogen bonds, augmented by π–π [centroid–centroid distance between adjacent pyridinium rings = 3.5807 (10) Å] and C—H⋯π interactions, giving a network structure. International Union of Crystallography 2008-02-27 /pmc/articles/PMC2960775/ /pubmed/21201959 http://dx.doi.org/10.1107/S1600536808004856 Text en © McAdam and Simpson 2008 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 McAdam, C. John Simpson, Jim 4-(Dimethylamino)pyridinium 4-toluenesulfonate |
title | 4-(Dimethylamino)pyridinium 4-toluenesulfonate |
title_full | 4-(Dimethylamino)pyridinium 4-toluenesulfonate |
title_fullStr | 4-(Dimethylamino)pyridinium 4-toluenesulfonate |
title_full_unstemmed | 4-(Dimethylamino)pyridinium 4-toluenesulfonate |
title_short | 4-(Dimethylamino)pyridinium 4-toluenesulfonate |
title_sort | 4-(dimethylamino)pyridinium 4-toluenesulfonate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960775/ https://www.ncbi.nlm.nih.gov/pubmed/21201959 http://dx.doi.org/10.1107/S1600536808004856 |
work_keys_str_mv | AT mcadamcjohn 4dimethylaminopyridinium4toluenesulfonate AT simpsonjim 4dimethylaminopyridinium4toluenesulfonate |