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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...

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Detalles Bibliográficos
Autores principales: Koch, Christian, Görls, Helmar, Westerhausen, Matthias
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
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)°
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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
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AT gorlshelmar 2benzoylaminomethylpyridiniumchloride
AT westerhausenmatthias 2benzoylaminomethylpyridiniumchloride