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Benzylammonium heptanoate–heptanoic acid (1/1)
The title salt, C(7)H(10)N(+)·C(7)H(13)O(2) (−)·C(7)H(14)O(2), is an unusual 2:1 stoichiometric combination of two carboxylic acid molecules and one amine. Although there are crystal structures of a number of 1:1 complexes reported in the literature, 2:1 acid amine complexes are rather uncommon....
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588549/ https://www.ncbi.nlm.nih.gov/pubmed/23476539 http://dx.doi.org/10.1107/S1600536813003012 |
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author | Wood, Mary H. Clarke, Stuart M. |
author_facet | Wood, Mary H. Clarke, Stuart M. |
author_sort | Wood, Mary H. |
collection | PubMed |
description | The title salt, C(7)H(10)N(+)·C(7)H(13)O(2) (−)·C(7)H(14)O(2), is an unusual 2:1 stoichiometric combination of two carboxylic acid molecules and one amine. Although there are crystal structures of a number of 1:1 complexes reported in the literature, 2:1 acid amine complexes are rather uncommon. In this case, a proton is transferred between one acid molecule and the amine to give an acid anion and an ammonium cation whilst the other carboxylic acid remains protonated. The species interact strongly via electrostatic forces and hydrogen bonds. In addition we note that the N atom of the ammonium group makes four close contacts to surrounding O atoms. Three of these are hydrogen bonds with neighbouring acid anions while the fourth does not involve a hydrogen atom but is directed towards the carbonyl O atom of the protonated acid. Each of the acid anion O atoms accepts two hydrogen bonds from adjacent N atoms. There is also evidence of short C—H⋯O contacts. There is disorder (occupancy ratio 0.51:0.49) in the alkyl chain of one of the carboxylic acid molecules. |
format | Online Article Text |
id | pubmed-3588549 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-35885492013-03-08 Benzylammonium heptanoate–heptanoic acid (1/1) Wood, Mary H. Clarke, Stuart M. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title salt, C(7)H(10)N(+)·C(7)H(13)O(2) (−)·C(7)H(14)O(2), is an unusual 2:1 stoichiometric combination of two carboxylic acid molecules and one amine. Although there are crystal structures of a number of 1:1 complexes reported in the literature, 2:1 acid amine complexes are rather uncommon. In this case, a proton is transferred between one acid molecule and the amine to give an acid anion and an ammonium cation whilst the other carboxylic acid remains protonated. The species interact strongly via electrostatic forces and hydrogen bonds. In addition we note that the N atom of the ammonium group makes four close contacts to surrounding O atoms. Three of these are hydrogen bonds with neighbouring acid anions while the fourth does not involve a hydrogen atom but is directed towards the carbonyl O atom of the protonated acid. Each of the acid anion O atoms accepts two hydrogen bonds from adjacent N atoms. There is also evidence of short C—H⋯O contacts. There is disorder (occupancy ratio 0.51:0.49) in the alkyl chain of one of the carboxylic acid molecules. International Union of Crystallography 2013-02-06 /pmc/articles/PMC3588549/ /pubmed/23476539 http://dx.doi.org/10.1107/S1600536813003012 Text en © Wood and Clarke 2013 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 Wood, Mary H. Clarke, Stuart M. Benzylammonium heptanoate–heptanoic acid (1/1) |
title | Benzylammonium heptanoate–heptanoic acid (1/1) |
title_full | Benzylammonium heptanoate–heptanoic acid (1/1) |
title_fullStr | Benzylammonium heptanoate–heptanoic acid (1/1) |
title_full_unstemmed | Benzylammonium heptanoate–heptanoic acid (1/1) |
title_short | Benzylammonium heptanoate–heptanoic acid (1/1) |
title_sort | benzylammonium heptanoate–heptanoic acid (1/1) |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588549/ https://www.ncbi.nlm.nih.gov/pubmed/23476539 http://dx.doi.org/10.1107/S1600536813003012 |
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