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

The title salt, C(8)H(20)N(+)center dot 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 sa...

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Bibliographic Details
Main Authors: Alhadi, A.A., Khaledi, H., Ali, H.M., Olmstead, M.M.
Format: Article
Published: Wiley-Blackwell 2010
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Online Access:http://eprints.um.edu.my/12421/
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Summary:The title salt, C(8)H(20)N(+)center dot 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 center dot center dot center dot 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)degrees.