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2-(Benzoylaminomethyl)pyridinium chloride
The title compound, C(13)H(13)N(2)O(+)·Cl(−), (1), was obtained as a colorless crystalline by-product during the synthesis of N-(2-pyridylmethyl)benzoylamine (2). The C—O bond length of 1.231 (2) Å in the benzoyl unit of (1) is slightly elongated in comparison with isolated C=O double bonds as als...
Autores principales: | , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2008
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2959924/ https://www.ncbi.nlm.nih.gov/pubmed/21581331 http://dx.doi.org/10.1107/S1600536808037021 |
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author | Koch, Christian Görls, Helmar Westerhausen, Matthias |
author_facet | Koch, Christian Görls, Helmar Westerhausen, Matthias |
author_sort | Koch, Christian |
collection | PubMed |
description | The title compound, C(13)H(13)N(2)O(+)·Cl(−), (1), was obtained as a colorless crystalline by-product during the synthesis of N-(2-pyridylmethyl)benzoylamine (2). The C—O bond length of 1.231 (2) Å in the benzoyl unit of (1) is slightly elongated in comparison with isolated C=O double bonds as also observed for (2) [1.237 (2) Å]. The N—C bond length of 1.345 (2) Å in the benzoic acid amide unit indicates the formation of an allylic O—C—N system and is very similar to the N—C bond lengths [1.345 (2) Å] of the pyridyl group. A further delocalization of charge from this allylic system into the phenyl fragment does not occur, which can be deduced from a characterisitc C—C single bond length of 1.499 (2) Å between these fragments. A dimer is formed via N—H⋯Cl hydrogen bonds. The two rings make a dihedral angle of 105.0 (2)° |
format | Text |
id | pubmed-2959924 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29599242010-12-30 2-(Benzoylaminomethyl)pyridinium chloride Koch, Christian Görls, Helmar Westerhausen, Matthias Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(13)H(13)N(2)O(+)·Cl(−), (1), was obtained as a colorless crystalline by-product during the synthesis of N-(2-pyridylmethyl)benzoylamine (2). The C—O bond length of 1.231 (2) Å in the benzoyl unit of (1) is slightly elongated in comparison with isolated C=O double bonds as also observed for (2) [1.237 (2) Å]. The N—C bond length of 1.345 (2) Å in the benzoic acid amide unit indicates the formation of an allylic O—C—N system and is very similar to the N—C bond lengths [1.345 (2) Å] of the pyridyl group. A further delocalization of charge from this allylic system into the phenyl fragment does not occur, which can be deduced from a characterisitc C—C single bond length of 1.499 (2) Å between these fragments. A dimer is formed via N—H⋯Cl hydrogen bonds. The two rings make a dihedral angle of 105.0 (2)° International Union of Crystallography 2008-11-13 /pmc/articles/PMC2959924/ /pubmed/21581331 http://dx.doi.org/10.1107/S1600536808037021 Text en © Koch et al. 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 Koch, Christian Görls, Helmar Westerhausen, Matthias 2-(Benzoylaminomethyl)pyridinium chloride |
title | 2-(Benzoylaminomethyl)pyridinium chloride |
title_full | 2-(Benzoylaminomethyl)pyridinium chloride |
title_fullStr | 2-(Benzoylaminomethyl)pyridinium chloride |
title_full_unstemmed | 2-(Benzoylaminomethyl)pyridinium chloride |
title_short | 2-(Benzoylaminomethyl)pyridinium chloride |
title_sort | 2-(benzoylaminomethyl)pyridinium chloride |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2959924/ https://www.ncbi.nlm.nih.gov/pubmed/21581331 http://dx.doi.org/10.1107/S1600536808037021 |
work_keys_str_mv | AT kochchristian 2benzoylaminomethylpyridiniumchloride AT gorlshelmar 2benzoylaminomethylpyridiniumchloride AT westerhausenmatthias 2benzoylaminomethylpyridiniumchloride |