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Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and o-, m- and p-aminobenzoic acid
Treatment of 3-formylacetylacetone with the isomeric o-, m- and p-aminobenzoic acids led to the formation of the corresponding Schiff bases, namely, 3-[(2-carboxyphenylamino)methylidene]pentane-2,4-dione, 1, 3-[(3-carboxyphenylamino)methylidene]pentane-2,4-dione, 2, and 3-[(4-carboxyp...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8739200/ https://www.ncbi.nlm.nih.gov/pubmed/35079425 http://dx.doi.org/10.1107/S2056989021013050 |
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author | Halz, Jan Henrik Hentsch, Andreas Wagner, Christoph Merzweiler, Kurt |
author_facet | Halz, Jan Henrik Hentsch, Andreas Wagner, Christoph Merzweiler, Kurt |
author_sort | Halz, Jan Henrik |
collection | PubMed |
description | Treatment of 3-formylacetylacetone with the isomeric o-, m- and p-aminobenzoic acids led to the formation of the corresponding Schiff bases, namely, 3-[(2-carboxyphenylamino)methylidene]pentane-2,4-dione, 1, 3-[(3-carboxyphenylamino)methylidene]pentane-2,4-dione, 2, and 3-[(4-carboxyphenylamino)methylidene]pentane-2,4-dione, 3, all C(13)H(13)NO(4), that contain a planar amino-methylene-pentane-2,4-dione core with a strong intramolecular N—H⋯O hydrogen bridge. The carboxyphenyl groups attached to the nitrogen atom are almost coplanar to the central molecular fragment. Depending on the position of the carboxyl unit, different supramolecular structures with hydrogen-bonding networks are formed in the three title structures. |
format | Online Article Text |
id | pubmed-8739200 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-87392002022-01-24 Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and o-, m- and p-aminobenzoic acid Halz, Jan Henrik Hentsch, Andreas Wagner, Christoph Merzweiler, Kurt Acta Crystallogr E Crystallogr Commun Research Communications Treatment of 3-formylacetylacetone with the isomeric o-, m- and p-aminobenzoic acids led to the formation of the corresponding Schiff bases, namely, 3-[(2-carboxyphenylamino)methylidene]pentane-2,4-dione, 1, 3-[(3-carboxyphenylamino)methylidene]pentane-2,4-dione, 2, and 3-[(4-carboxyphenylamino)methylidene]pentane-2,4-dione, 3, all C(13)H(13)NO(4), that contain a planar amino-methylene-pentane-2,4-dione core with a strong intramolecular N—H⋯O hydrogen bridge. The carboxyphenyl groups attached to the nitrogen atom are almost coplanar to the central molecular fragment. Depending on the position of the carboxyl unit, different supramolecular structures with hydrogen-bonding networks are formed in the three title structures. International Union of Crystallography 2022-01-01 /pmc/articles/PMC8739200/ /pubmed/35079425 http://dx.doi.org/10.1107/S2056989021013050 Text en © Halz et al. 2022 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Research Communications Halz, Jan Henrik Hentsch, Andreas Wagner, Christoph Merzweiler, Kurt Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and o-, m- and p-aminobenzoic acid |
title | Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and o-, m- and p-aminobenzoic acid |
title_full | Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and o-, m- and p-aminobenzoic acid |
title_fullStr | Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and o-, m- and p-aminobenzoic acid |
title_full_unstemmed | Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and o-, m- and p-aminobenzoic acid |
title_short | Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone and o-, m- and p-aminobenzoic acid |
title_sort | synthesis and crystal structures of three schiff bases derived from 3-formylacetylacetone and o-, m- and p-aminobenzoic acid |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8739200/ https://www.ncbi.nlm.nih.gov/pubmed/35079425 http://dx.doi.org/10.1107/S2056989021013050 |
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