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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...

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Autores principales: Wink, Christoph, Schollmeyer, Dieter, Detert, Heiner
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
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.
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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
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