2,5-Bis[4-(dimethyl­amino)­phen­yl]-3,6-dimethyl­pyrazine

The title compound, C(22)H(26)N(4), was prepared from p-dimethyl­amino­propiophenone in six steps. The mol­ecule has no crystallographic symmetry. The dihedral angles between the pyrazine ring and the phenyl rings are 35.81 (6) and 37.11 (8)°. The dimethyl­amino groups are essentially planar (sum of...

Descripción completa

Detalles Bibliográficos
Autores principales: Moschel, Sebastian, Schollmeyer, Dieter, Detert, Heiner
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3120404/
https://www.ncbi.nlm.nih.gov/pubmed/21754805
http://dx.doi.org/10.1107/S160053681101748X
_version_ 1782206671641116672
author Moschel, Sebastian
Schollmeyer, Dieter
Detert, Heiner
author_facet Moschel, Sebastian
Schollmeyer, Dieter
Detert, Heiner
author_sort Moschel, Sebastian
collection PubMed
description The title compound, C(22)H(26)N(4), was prepared from p-dimethyl­amino­propiophenone in six steps. The mol­ecule has no crystallographic symmetry. The dihedral angles between the pyrazine ring and the phenyl rings are 35.81 (6) and 37.11 (8)°. The dimethyl­amino groups are essentially planar (sum of the bond angles at N = 359.3 and 359.9°) and nearly coplanar with the adjacent aromatic ring [dihedral angles = 5.54 (11) and 7.40 (3)°]. This effect and the short aniline C—N bonds can be rationalised in terms of charge transfer from the amino groups to the central pyrazine ring.
format Online
Article
Text
id pubmed-3120404
institution National Center for Biotechnology Information
language English
publishDate 2011
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-31204042011-07-13 2,5-Bis[4-(dimethyl­amino)­phen­yl]-3,6-dimethyl­pyrazine Moschel, Sebastian Schollmeyer, Dieter Detert, Heiner Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(22)H(26)N(4), was prepared from p-dimethyl­amino­propiophenone in six steps. The mol­ecule has no crystallographic symmetry. The dihedral angles between the pyrazine ring and the phenyl rings are 35.81 (6) and 37.11 (8)°. The dimethyl­amino groups are essentially planar (sum of the bond angles at N = 359.3 and 359.9°) and nearly coplanar with the adjacent aromatic ring [dihedral angles = 5.54 (11) and 7.40 (3)°]. This effect and the short aniline C—N bonds can be rationalised in terms of charge transfer from the amino groups to the central pyrazine ring. International Union of Crystallography 2011-05-14 /pmc/articles/PMC3120404/ /pubmed/21754805 http://dx.doi.org/10.1107/S160053681101748X Text en © Moschel et al. 2011 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
Moschel, Sebastian
Schollmeyer, Dieter
Detert, Heiner
2,5-Bis[4-(dimethyl­amino)­phen­yl]-3,6-dimethyl­pyrazine
title 2,5-Bis[4-(dimethyl­amino)­phen­yl]-3,6-dimethyl­pyrazine
title_full 2,5-Bis[4-(dimethyl­amino)­phen­yl]-3,6-dimethyl­pyrazine
title_fullStr 2,5-Bis[4-(dimethyl­amino)­phen­yl]-3,6-dimethyl­pyrazine
title_full_unstemmed 2,5-Bis[4-(dimethyl­amino)­phen­yl]-3,6-dimethyl­pyrazine
title_short 2,5-Bis[4-(dimethyl­amino)­phen­yl]-3,6-dimethyl­pyrazine
title_sort 2,5-bis[4-(dimethyl­amino)­phen­yl]-3,6-dimethyl­pyrazine
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3120404/
https://www.ncbi.nlm.nih.gov/pubmed/21754805
http://dx.doi.org/10.1107/S160053681101748X
work_keys_str_mv AT moschelsebastian 25bis4dimethylaminophenyl36dimethylpyrazine
AT schollmeyerdieter 25bis4dimethylaminophenyl36dimethylpyrazine
AT detertheiner 25bis4dimethylaminophenyl36dimethylpyrazine

Ejemplares similares