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, C 13 H 15 NO 2 ( 1 ), 3-[( tert -butylamino)methylidene]pentan-2,4-dione, C 10 H 17 NO 2...

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Bibliographic Details
Published in:Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2023-08, Vol.79 (8), p.707-713
Main Authors: Halz, Jan Henrik, Hentsch, Andreas, Wagner, Christoph, Merzweiler, Kurt
Format: Article
Language:English
Subjects:
3-formylacetylacetone
crystal structure
enamine
schiff base
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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, C 13 H 15 NO 2 ( 1 ), 3-[( tert -butylamino)methylidene]pentan-2,4-dione, C 10 H 17 NO 2 ( 2 ) and 3-{[( S )-benzyl(methyl)amino]methylidene}pentane-2,4-dione, C 14 H 17 NO 2 ( 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
2056-9890
DOI:10.1107/S205698902300587X