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(Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-ylidene)acetate
The title compound, C(19)H(19)NO(2), obtained as an almost equimolar mixture (as shown by (1)H NMR) with the E isomer through a Wittig reaction between 4-amino-9H-fluoren-9-one and the stabilized ylide Ph(3)P=CHCO(2)C(CH(3))(3), was obtained pure in the Z configuration following crystallization from...
Autores principales: | , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2008
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2959429/ https://www.ncbi.nlm.nih.gov/pubmed/21201178 http://dx.doi.org/10.1107/S1600536808029735 |
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author | Krokidis, Marios Papaioannou, Dionissios Nastopoulos, Vassilios |
author_facet | Krokidis, Marios Papaioannou, Dionissios Nastopoulos, Vassilios |
author_sort | Krokidis, Marios |
collection | PubMed |
description | The title compound, C(19)H(19)NO(2), obtained as an almost equimolar mixture (as shown by (1)H NMR) with the E isomer through a Wittig reaction between 4-amino-9H-fluoren-9-one and the stabilized ylide Ph(3)P=CHCO(2)C(CH(3))(3), was obtained pure in the Z configuration following crystallization from toluene. The molecule shows a planar arrangement of the ring system and the new double bond, whereas the carbonyl O atom forms a 45.1 (3)° dihedral angle with it. The molecules are linked by N—H⋯O hydrogen bonds, forming cyclic structures with R (4) (4)(24) graph-set motifs. These motifs are connected to each other, giving rise to a sheet structure parallel to the ab plane. The linkage within the sheets is further enhanced by π–π stacking interactions between the fluorene units [centroid–centroid distance = 3.583 (2) Å]. |
format | Text |
id | pubmed-2959429 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29594292010-12-30 (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-ylidene)acetate Krokidis, Marios Papaioannou, Dionissios Nastopoulos, Vassilios Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(19)NO(2), obtained as an almost equimolar mixture (as shown by (1)H NMR) with the E isomer through a Wittig reaction between 4-amino-9H-fluoren-9-one and the stabilized ylide Ph(3)P=CHCO(2)C(CH(3))(3), was obtained pure in the Z configuration following crystallization from toluene. The molecule shows a planar arrangement of the ring system and the new double bond, whereas the carbonyl O atom forms a 45.1 (3)° dihedral angle with it. The molecules are linked by N—H⋯O hydrogen bonds, forming cyclic structures with R (4) (4)(24) graph-set motifs. These motifs are connected to each other, giving rise to a sheet structure parallel to the ab plane. The linkage within the sheets is further enhanced by π–π stacking interactions between the fluorene units [centroid–centroid distance = 3.583 (2) Å]. International Union of Crystallography 2008-09-20 /pmc/articles/PMC2959429/ /pubmed/21201178 http://dx.doi.org/10.1107/S1600536808029735 Text en © Krokidis et al. 2008 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 Krokidis, Marios Papaioannou, Dionissios Nastopoulos, Vassilios (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-ylidene)acetate |
title | (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-ylidene)acetate |
title_full | (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-ylidene)acetate |
title_fullStr | (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-ylidene)acetate |
title_full_unstemmed | (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-ylidene)acetate |
title_short | (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-ylidene)acetate |
title_sort | (z)-tert-butyl 2-(4-amino-9h-fluoren-9-ylidene)acetate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2959429/ https://www.ncbi.nlm.nih.gov/pubmed/21201178 http://dx.doi.org/10.1107/S1600536808029735 |
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