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5-Amino-1-methyl-1H-benzimidazole

The structure of the title compound, C(8)H(9)N(3), a potential anti­tumour drug, was determined in order to give more insight into its structure–function relationships. The benzimidazole core of the mol­ecule was found to be exactly planar, while the substituents are displaced slightly from the mol­...

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Detalles Bibliográficos
Autores principales: Lokaj, Jan, Kettmann, Viktor, Milata, Viktor, Solčan, Tomáš
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977244/
https://www.ncbi.nlm.nih.gov/pubmed/21583494
http://dx.doi.org/10.1107/S1600536809025550
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author Lokaj, Jan
Kettmann, Viktor
Milata, Viktor
Solčan, Tomáš
author_facet Lokaj, Jan
Kettmann, Viktor
Milata, Viktor
Solčan, Tomáš
author_sort Lokaj, Jan
collection PubMed
description The structure of the title compound, C(8)H(9)N(3), a potential anti­tumour drug, was determined in order to give more insight into its structure–function relationships. The benzimidazole core of the mol­ecule was found to be exactly planar, while the substituents are displaced slightly from the mol­ecular plane [C—C—N—C and C—C—C—N torsion angles of 0.8 (3) and 179.0 (1)° for the methyl and amino groups, respectively]. The bond lengths are analysed in detail and compared with those of the parent unsubstituted analogues. The results show that the lone-pair electrons on the amino N atom are involved in conjugation with the adjacent π system and hence affect the charge distribution in the heterocycle. Two inter­molecular N—H⋯N and C—H⋯N hydrogen bonds have been identified.
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spelling pubmed-29772442010-12-30 5-Amino-1-methyl-1H-benzimidazole Lokaj, Jan Kettmann, Viktor Milata, Viktor Solčan, Tomáš Acta Crystallogr Sect E Struct Rep Online Organic Papers The structure of the title compound, C(8)H(9)N(3), a potential anti­tumour drug, was determined in order to give more insight into its structure–function relationships. The benzimidazole core of the mol­ecule was found to be exactly planar, while the substituents are displaced slightly from the mol­ecular plane [C—C—N—C and C—C—C—N torsion angles of 0.8 (3) and 179.0 (1)° for the methyl and amino groups, respectively]. The bond lengths are analysed in detail and compared with those of the parent unsubstituted analogues. The results show that the lone-pair electrons on the amino N atom are involved in conjugation with the adjacent π system and hence affect the charge distribution in the heterocycle. Two inter­molecular N—H⋯N and C—H⋯N hydrogen bonds have been identified. International Union of Crystallography 2009-07-08 /pmc/articles/PMC2977244/ /pubmed/21583494 http://dx.doi.org/10.1107/S1600536809025550 Text en © Lokaj et al. 2009 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
Lokaj, Jan
Kettmann, Viktor
Milata, Viktor
Solčan, Tomáš
5-Amino-1-methyl-1H-benzimidazole
title 5-Amino-1-methyl-1H-benzimidazole
title_full 5-Amino-1-methyl-1H-benzimidazole
title_fullStr 5-Amino-1-methyl-1H-benzimidazole
title_full_unstemmed 5-Amino-1-methyl-1H-benzimidazole
title_short 5-Amino-1-methyl-1H-benzimidazole
title_sort 5-amino-1-methyl-1h-benzimidazole
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977244/
https://www.ncbi.nlm.nih.gov/pubmed/21583494
http://dx.doi.org/10.1107/S1600536809025550
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