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2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methylpropanenitrile
The title compound, C(19)H(17)ClN(4), was obtained from the reaction of 3-chloro-5,6-diphenyl-1,2,4-triazine with isobutyronitrile in the presence of lithium diisopropylamide as an unexpected product of covalent addition of isobutyronitrile carbanion to the C-5 atom of the 1,2,4-triazine ring. The...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379491/ https://www.ncbi.nlm.nih.gov/pubmed/22719689 http://dx.doi.org/10.1107/S1600536812023252 |
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author | Wolińska, Ewa Karczmarzyk, Zbigniew Rykowski, Andrzej Urbańczyk-Lipkowska, Zofia Kalicki, Przemysław |
author_facet | Wolińska, Ewa Karczmarzyk, Zbigniew Rykowski, Andrzej Urbańczyk-Lipkowska, Zofia Kalicki, Przemysław |
author_sort | Wolińska, Ewa |
collection | PubMed |
description | The title compound, C(19)H(17)ClN(4), was obtained from the reaction of 3-chloro-5,6-diphenyl-1,2,4-triazine with isobutyronitrile in the presence of lithium diisopropylamide as an unexpected product of covalent addition of isobutyronitrile carbanion to the C-5 atom of the 1,2,4-triazine ring. The 2,5-dihydro-1,2,4-triazine ring is essentially planar (r.m.s. deviation = 0.0059 Å) and the 5- and 6-phenyl substituents are inclined to its mean plane with dihedral angles of 89.97 (4) and 55.52 (5)°, respectively. Intramolecular C—H⋯N interactions occur. In the crystal, molecules related by a c-glide plane are linked into zigzag chains along [001] by N—H⋯N hydrogen bonds. |
format | Online Article Text |
id | pubmed-3379491 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-33794912012-06-20 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methylpropanenitrile Wolińska, Ewa Karczmarzyk, Zbigniew Rykowski, Andrzej Urbańczyk-Lipkowska, Zofia Kalicki, Przemysław Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(17)ClN(4), was obtained from the reaction of 3-chloro-5,6-diphenyl-1,2,4-triazine with isobutyronitrile in the presence of lithium diisopropylamide as an unexpected product of covalent addition of isobutyronitrile carbanion to the C-5 atom of the 1,2,4-triazine ring. The 2,5-dihydro-1,2,4-triazine ring is essentially planar (r.m.s. deviation = 0.0059 Å) and the 5- and 6-phenyl substituents are inclined to its mean plane with dihedral angles of 89.97 (4) and 55.52 (5)°, respectively. Intramolecular C—H⋯N interactions occur. In the crystal, molecules related by a c-glide plane are linked into zigzag chains along [001] by N—H⋯N hydrogen bonds. International Union of Crystallography 2012-05-31 /pmc/articles/PMC3379491/ /pubmed/22719689 http://dx.doi.org/10.1107/S1600536812023252 Text en © Wolińska et al. 2012 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 Wolińska, Ewa Karczmarzyk, Zbigniew Rykowski, Andrzej Urbańczyk-Lipkowska, Zofia Kalicki, Przemysław 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methylpropanenitrile |
title | 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methylpropanenitrile |
title_full | 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methylpropanenitrile |
title_fullStr | 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methylpropanenitrile |
title_full_unstemmed | 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methylpropanenitrile |
title_short | 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methylpropanenitrile |
title_sort | 2-(3-chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methylpropanenitrile |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379491/ https://www.ncbi.nlm.nih.gov/pubmed/22719689 http://dx.doi.org/10.1107/S1600536812023252 |
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