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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....

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Autores principales: Wood, Mary H., Clarke, Stuart M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
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.
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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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