Cargando…
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...
Autores principales: | , , , |
---|---|
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 |
_version_ | 1782191061710405632 |
---|---|
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. |
format | Text |
id | pubmed-2977244 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT lokajjan 5amino1methyl1hbenzimidazole AT kettmannviktor 5amino1methyl1hbenzimidazole AT milataviktor 5amino1methyl1hbenzimidazole AT solcantomas 5amino1methyl1hbenzimidazole |