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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...

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Autores principales: Halz, Jan Henrik, Hentsch, Andreas, Wagner, Christoph, Merzweiler, Kurt
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2022
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.
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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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