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Updated: May 26, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
4-Diethyl-amino-3,5-diisopropyl-benzalde-hyde
Christoph Wink1, Dieter Schollmeyer, Heiner Detert
1University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany.
Abstract:
The title benzaldehyde, C(17)H(27)NO, was prepared via lithia-tion 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 phenyl-ene 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 phenyl-ene 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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