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4-Diethylamino-3,5-diisopropylbenzaldehyde
The title benzaldehyde, C(17)H(27)NO, was prepared via lithiation of bromoaniline and reaction with DMF. In the crystal, the molecule adopts a C2-symmetrical conformation; nevertheless, two modes of disorder are present: the orientation of the aldehyde group (occupancy ratio 0.5:0.5) and of symmetr...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3238983/ https://www.ncbi.nlm.nih.gov/pubmed/22199832 http://dx.doi.org/10.1107/S1600536811047672 |
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author | Wink, Christoph Schollmeyer, Dieter Detert, Heiner |
author_facet | Wink, Christoph Schollmeyer, Dieter Detert, Heiner |
author_sort | Wink, Christoph |
collection | PubMed |
description | The title benzaldehyde, C(17)H(27)NO, was prepared via lithiation of bromoaniline and reaction with DMF. In the crystal, the molecule adopts a C2-symmetrical conformation; nevertheless, two modes of disorder are present: the orientation of the aldehyde group (occupancy ratio 0.5:0.5) and of symmetry-equivalent ethyl groups [occupancy ratio 0.595 (7):0.405 (7)]. The phenylene ring and the carbonyl group are essentially coplanar [C—C—C—O torsion angle = −179.0 (4)°] but the dihedral angle between the mean planes of the phenylene ring and the amino group = 67.5 (2)°. This and the long [1.414 (3) Å] aniline C—N bond indicate electronic decoupling between the carbonyl and amino groups. The angle sum of 359.9 (2)° around the N atom results from steric compression-induced rehybridization. |
format | Online Article Text |
id | pubmed-3238983 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32389832011-12-23 4-Diethylamino-3,5-diisopropylbenzaldehyde Wink, Christoph Schollmeyer, Dieter Detert, Heiner Acta Crystallogr Sect E Struct Rep Online Organic Papers The title benzaldehyde, C(17)H(27)NO, was prepared via lithiation of bromoaniline and reaction with DMF. In the crystal, the molecule adopts a C2-symmetrical conformation; nevertheless, two modes of disorder are present: the orientation of the aldehyde group (occupancy ratio 0.5:0.5) and of symmetry-equivalent ethyl groups [occupancy ratio 0.595 (7):0.405 (7)]. The phenylene ring and the carbonyl group are essentially coplanar [C—C—C—O torsion angle = −179.0 (4)°] but the dihedral angle between the mean planes of the phenylene ring and the amino group = 67.5 (2)°. This and the long [1.414 (3) Å] aniline C—N bond indicate electronic decoupling between the carbonyl and amino groups. The angle sum of 359.9 (2)° around the N atom results from steric compression-induced rehybridization. International Union of Crystallography 2011-11-16 /pmc/articles/PMC3238983/ /pubmed/22199832 http://dx.doi.org/10.1107/S1600536811047672 Text en © Wink 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 Wink, Christoph Schollmeyer, Dieter Detert, Heiner 4-Diethylamino-3,5-diisopropylbenzaldehyde |
title | 4-Diethylamino-3,5-diisopropylbenzaldehyde |
title_full | 4-Diethylamino-3,5-diisopropylbenzaldehyde |
title_fullStr | 4-Diethylamino-3,5-diisopropylbenzaldehyde |
title_full_unstemmed | 4-Diethylamino-3,5-diisopropylbenzaldehyde |
title_short | 4-Diethylamino-3,5-diisopropylbenzaldehyde |
title_sort | 4-diethylamino-3,5-diisopropylbenzaldehyde |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3238983/ https://www.ncbi.nlm.nih.gov/pubmed/22199832 http://dx.doi.org/10.1107/S1600536811047672 |
work_keys_str_mv | AT winkchristoph 4diethylamino35diisopropylbenzaldehyde AT schollmeyerdieter 4diethylamino35diisopropylbenzaldehyde AT detertheiner 4diethylamino35diisopropylbenzaldehyde |