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Dimethylammonium 2,4,5-tricarboxybenzoate: an example of the decarbonylation of N,N-dimethylformamide in the presence of a metal and a benzenepolycarboxylic acid. Is zirconium(IV) the Tsotsi?
The title salt, C(2)H(8)N(+)·C(10)H(5)O(8) (−), was the unexpected product of an attempt to prepare a Zr(IV) metal–organic framework with benzene-1,2,4,5-tetracarboxylic acid (1,2,4,5-H(3)B4C). In the reaction, the DMF solvent has been decarbonylated, forming the dimethylammonium cation, wit...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5095824/ https://www.ncbi.nlm.nih.gov/pubmed/27840699 http://dx.doi.org/10.1107/S2056989016014948 |
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author | Hulushe, S. T. Hosten, E. C. Watkins, G. M. |
author_facet | Hulushe, S. T. Hosten, E. C. Watkins, G. M. |
author_sort | Hulushe, S. T. |
collection | PubMed |
description | The title salt, C(2)H(8)N(+)·C(10)H(5)O(8) (−), was the unexpected product of an attempt to prepare a Zr(IV) metal–organic framework with benzene-1,2,4,5-tetracarboxylic acid (1,2,4,5-H(3)B4C). In the reaction, the DMF solvent has been decarbonylated, forming the dimethylammonium cation, with one proton lost from the tetracarboxylic acid. It is proposed that the Zr(IV) salt acts as a Tsotsi or robber, plundering CO from the DMF molecule. The resulting salt crystallizes with two cations and two anions in the asymmetric unit. An intramolecular hydrogen bond forms between a carboxylic acid substituent and the carboxylate group of each of the monodeprotonated (1,2,4,5-H(3)B4C(−)) anions. In the crystal, an extensive array of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds generates a three-dimensional network, with columns of cations and anions forming along the b axis. |
format | Online Article Text |
id | pubmed-5095824 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-50958242016-11-11 Dimethylammonium 2,4,5-tricarboxybenzoate: an example of the decarbonylation of N,N-dimethylformamide in the presence of a metal and a benzenepolycarboxylic acid. Is zirconium(IV) the Tsotsi? Hulushe, S. T. Hosten, E. C. Watkins, G. M. Acta Crystallogr E Crystallogr Commun Research Communications The title salt, C(2)H(8)N(+)·C(10)H(5)O(8) (−), was the unexpected product of an attempt to prepare a Zr(IV) metal–organic framework with benzene-1,2,4,5-tetracarboxylic acid (1,2,4,5-H(3)B4C). In the reaction, the DMF solvent has been decarbonylated, forming the dimethylammonium cation, with one proton lost from the tetracarboxylic acid. It is proposed that the Zr(IV) salt acts as a Tsotsi or robber, plundering CO from the DMF molecule. The resulting salt crystallizes with two cations and two anions in the asymmetric unit. An intramolecular hydrogen bond forms between a carboxylic acid substituent and the carboxylate group of each of the monodeprotonated (1,2,4,5-H(3)B4C(−)) anions. In the crystal, an extensive array of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds generates a three-dimensional network, with columns of cations and anions forming along the b axis. International Union of Crystallography 2016-10-04 /pmc/articles/PMC5095824/ /pubmed/27840699 http://dx.doi.org/10.1107/S2056989016014948 Text en © Hulushe et al. 2016 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 | Research Communications Hulushe, S. T. Hosten, E. C. Watkins, G. M. Dimethylammonium 2,4,5-tricarboxybenzoate: an example of the decarbonylation of N,N-dimethylformamide in the presence of a metal and a benzenepolycarboxylic acid. Is zirconium(IV) the Tsotsi? |
title | Dimethylammonium 2,4,5-tricarboxybenzoate: an example of the decarbonylation of N,N-dimethylformamide in the presence of a metal and a benzenepolycarboxylic acid. Is zirconium(IV) the Tsotsi? |
title_full | Dimethylammonium 2,4,5-tricarboxybenzoate: an example of the decarbonylation of N,N-dimethylformamide in the presence of a metal and a benzenepolycarboxylic acid. Is zirconium(IV) the Tsotsi? |
title_fullStr | Dimethylammonium 2,4,5-tricarboxybenzoate: an example of the decarbonylation of N,N-dimethylformamide in the presence of a metal and a benzenepolycarboxylic acid. Is zirconium(IV) the Tsotsi? |
title_full_unstemmed | Dimethylammonium 2,4,5-tricarboxybenzoate: an example of the decarbonylation of N,N-dimethylformamide in the presence of a metal and a benzenepolycarboxylic acid. Is zirconium(IV) the Tsotsi? |
title_short | Dimethylammonium 2,4,5-tricarboxybenzoate: an example of the decarbonylation of N,N-dimethylformamide in the presence of a metal and a benzenepolycarboxylic acid. Is zirconium(IV) the Tsotsi? |
title_sort | dimethylammonium 2,4,5-tricarboxybenzoate: an example of the decarbonylation of n,n-dimethylformamide in the presence of a metal and a benzenepolycarboxylic acid. is zirconium(iv) the tsotsi? |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5095824/ https://www.ncbi.nlm.nih.gov/pubmed/27840699 http://dx.doi.org/10.1107/S2056989016014948 |
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