Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and benzyl-, tert-butyl- and (S)-methylbenzylamine

Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and benzyl-, tert-butyl- and (S)-methylbenzylamine

Treatment of 3-formylacetylacetone with the amines benzylamine, tert-butylamine and (S)-methylbenzylamine led to the formation of the corresponding Schiff bases 3-[(benzylamino)methylidene]pentane-2,4-dione, C13H15NO2 (1), 3-[(tert-butylamino)methylidene]pentan-2,4-dione, C10H17NO2 (2) and 3-{[(S)-b...

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Bibliographic Details
Main Authors: Jan Henrik Halz, Andreas Hentsch, Christoph Wagner, Kurt Merzweiler
Format: Article
Language:English
Published: International Union of Crystallography 2023-08-01
Series:Acta Crystallographica Section E: Crystallographic Communications
Subjects:
crystal structure
enamine
3-formylacetylacetone
schiff base
Online Access:http://scripts.iucr.org/cgi-bin/paper?S205698902300587X
Description
Summary:Treatment of 3-formylacetylacetone with the amines benzylamine, tert-butylamine and (S)-methylbenzylamine led to the formation of the corresponding Schiff bases 3-[(benzylamino)methylidene]pentane-2,4-dione, C13H15NO2 (1), 3-[(tert-butylamino)methylidene]pentan-2,4-dione, C10H17NO2 (2) and 3-{[(S)-benzyl(methyl)amino]methylidene}pentane-2,4-dione, C14H17NO2 (3). The molecules of all three compounds exist as enamine tautomers that contain a nearly planar amino-methylene-pentane-2,4-dione core with a strong intramolecular N—H...O hydrogen bridge. The R group attached to the enamine N atom has no significant influence on the bond lengths and angles of the amino-methylene-pentane-2,4-dione core. The supramolecular structures in 1–3 are mainly based on weak C—H...O hydrogen bonds.
ISSN:2056-9890

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