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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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2023-08-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S205698902300587X |
| _version_ | 1797692263928692736 |
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| author | Jan Henrik Halz Andreas Hentsch Christoph Wagner Kurt Merzweiler |
| author_facet | Jan Henrik Halz Andreas Hentsch Christoph Wagner Kurt Merzweiler |
| author_sort | Jan Henrik Halz |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-12T02:26:04Z |
| format | Article |
| id | doaj.art-7aee4dbe3cef4acfb0aceef1ebb4b297 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-03-12T02:26:04Z |
| publishDate | 2023-08-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-7aee4dbe3cef4acfb0aceef1ebb4b2972023-09-05T13:04:53ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902023-08-0179870771310.1107/S205698902300587Xwm5685Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and benzyl-, tert-butyl- and (S)-methylbenzylamineJan Henrik Halz0Andreas Hentsch1Christoph Wagner2Kurt Merzweiler3Martin-Luther-Universität Halle-Wittenberg, Naturwissenschaftliche Fakultät II, Institut für Chemie, D-06099 Halle, GermanyMartin-Luther-Universität Halle-Wittenberg, Naturwissenschaftliche Fakultät II, Institut für Chemie, D-06099 Halle, GermanyMartin-Luther-Universität Halle-Wittenberg, Naturwissenschaftliche Fakultät II, Institut für Chemie, D-06099 Halle, GermanyMartin-Luther-Universität Halle-Wittenberg, Naturwissenschaftliche Fakultät II, Institut für Chemie, D-06099 Halle, GermanyTreatment 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.http://scripts.iucr.org/cgi-bin/paper?S205698902300587Xcrystal structureenamine3-formylacetylacetoneschiff base |
| spellingShingle | Jan Henrik Halz Andreas Hentsch Christoph Wagner Kurt Merzweiler Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and benzyl-, tert-butyl- and (S)-methylbenzylamine Acta Crystallographica Section E: Crystallographic Communications crystal structure enamine 3-formylacetylacetone schiff base |
| title | Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and benzyl-, tert-butyl- and (S)-methylbenzylamine |
| title_full | Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and benzyl-, tert-butyl- and (S)-methylbenzylamine |
| title_fullStr | Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and benzyl-, tert-butyl- and (S)-methylbenzylamine |
| title_full_unstemmed | Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and benzyl-, tert-butyl- and (S)-methylbenzylamine |
| title_short | Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and benzyl-, tert-butyl- and (S)-methylbenzylamine |
| title_sort | synthesis and crystal structures of three schiff bases derived from 3 formylacetylacetone and benzyl tert butyl and s methylbenzylamine |
| topic | crystal structure enamine 3-formylacetylacetone schiff base |
| url | http://scripts.iucr.org/cgi-bin/paper?S205698902300587X |
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