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Di-n-butyl­ammonium 2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]benzoate

The title salt, C(8)H(20)N(+)·C(22)H(27)O(3)S(−), is a proton-transfer compound derived from the recently reported parent carb­oxy­lic acid [Alhadi et al. (2010). Acta Cryst. E66, o1787] by the addition of a second equivalent of di-n-butyl­amine, yielding the di-n-butyl­ammonium carboxyl­ate salt. T...

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Autores principales: Alhadi, Abeer A., Khaledi, Hamid, Mohd Ali, Hapipah, Olmstead, Marilyn M.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007956/
https://www.ncbi.nlm.nih.gov/pubmed/21588774
http://dx.doi.org/10.1107/S1600536810033921
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author Alhadi, Abeer A.
Khaledi, Hamid
Mohd Ali, Hapipah
Olmstead, Marilyn M.
author_facet Alhadi, Abeer A.
Khaledi, Hamid
Mohd Ali, Hapipah
Olmstead, Marilyn M.
author_sort Alhadi, Abeer A.
collection PubMed
description The title salt, C(8)H(20)N(+)·C(22)H(27)O(3)S(−), is a proton-transfer compound derived from the recently reported parent carb­oxy­lic acid [Alhadi et al. (2010). Acta Cryst. E66, o1787] by the addition of a second equivalent of di-n-butyl­amine, yielding the di-n-butyl­ammonium carboxyl­ate salt. The structure of the carboxyl­ate anion resembles that of the parent carb­oxy­lic acid. The main difference lies in the position of the H atom in the 4-hy­droxy group. In the anion the O—H bond is perpendicular, rather than parallel, to the benzyl ring. This position appears to facilitate hydrogen bonding to an O atom of the carboxyl­ate group of a symmetry-related anion. In addition, there are three N—H⋯O hydrogen bonds. In contrast, the neutral species hydrogen bonds via a carboxylic acid dimer. The dihedral angle between the benzene rings in the anion is 79.19 (7)°.
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spelling pubmed-30079562010-12-30 Di-n-butyl­ammonium 2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]benzoate Alhadi, Abeer A. Khaledi, Hamid Mohd Ali, Hapipah Olmstead, Marilyn M. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title salt, C(8)H(20)N(+)·C(22)H(27)O(3)S(−), is a proton-transfer compound derived from the recently reported parent carb­oxy­lic acid [Alhadi et al. (2010). Acta Cryst. E66, o1787] by the addition of a second equivalent of di-n-butyl­amine, yielding the di-n-butyl­ammonium carboxyl­ate salt. The structure of the carboxyl­ate anion resembles that of the parent carb­oxy­lic acid. The main difference lies in the position of the H atom in the 4-hy­droxy group. In the anion the O—H bond is perpendicular, rather than parallel, to the benzyl ring. This position appears to facilitate hydrogen bonding to an O atom of the carboxyl­ate group of a symmetry-related anion. In addition, there are three N—H⋯O hydrogen bonds. In contrast, the neutral species hydrogen bonds via a carboxylic acid dimer. The dihedral angle between the benzene rings in the anion is 79.19 (7)°. International Union of Crystallography 2010-08-28 /pmc/articles/PMC3007956/ /pubmed/21588774 http://dx.doi.org/10.1107/S1600536810033921 Text en © Alhadi et al. 2010 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
Alhadi, Abeer A.
Khaledi, Hamid
Mohd Ali, Hapipah
Olmstead, Marilyn M.
Di-n-butyl­ammonium 2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]benzoate
title Di-n-butyl­ammonium 2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]benzoate
title_full Di-n-butyl­ammonium 2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]benzoate
title_fullStr Di-n-butyl­ammonium 2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]benzoate
title_full_unstemmed Di-n-butyl­ammonium 2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]benzoate
title_short Di-n-butyl­ammonium 2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]benzoate
title_sort di-n-butyl­ammonium 2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]benzoate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007956/
https://www.ncbi.nlm.nih.gov/pubmed/21588774
http://dx.doi.org/10.1107/S1600536810033921
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