Structure and thermodynamics of a multimeric cavitand assembly

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dc.contributor.author Aakeröy, Christer B.
dc.contributor.author Chopade, Prashant D.
dc.contributor.author Quinn, Colette F.
dc.contributor.author Desper, John
dc.date.accessioned 2014-06-20T13:33:02Z
dc.date.available 2014-06-20T13:33:02Z
dc.date.issued 2014-06-20
dc.identifier.uri http://hdl.handle.net/2097/17868
dc.description.abstract A set of COOH···N(pyridine) 5 hydrogen bonds have been utilized in the targeted synthesis of a cavitand-based assembly. A cavitand appended with four pyridyl groups was synthesized from a Suzuki coupling of a tetrabromocavitand and 3-pyridyl boronic acid. The product resulting from the reaction between the tetra-pyridyl cavitand and 4-nitrobenzoic acid was investigated in solution using isothermal titration calorimetry (ITC) under equilibrium conditions, and in the solid state through single-crystal X-ray diffraction and infrared spectroscopy. The results show that the targeted pentameric hydrogen-bonded architecture was isolated in the solid-state, and the infrared spectroscopy confirm the presence of COOH···N(py) interactions. The same assembly, with a 1:4 cavitand:acid stoichiometry, is also present in solution in acetonitrile and the enthalpy of binding for this reaction is approximately -45 kJ/mol. en_US
dc.language.iso en_US en_US
dc.relation.uri http://dx.doi.org/10.1039/C3CE42447B en_US
dc.subject Multimeric cavitand assembly en_US
dc.subject Cavitand en_US
dc.subject X-ray diffraction en_US
dc.subject Infrared spectroscopy en_US
dc.title Structure and thermodynamics of a multimeric cavitand assembly en_US
dc.type Article (author version) en_US
dc.date.published 2014 en_US
dc.citation.doi doi:10.1039/c3ce42447b en_US
dc.citation.epage 3801 en_US
dc.citation.issue 18 en_US
dc.citation.jtitle CrystEngComm en_US
dc.citation.spage 3796 en_US
dc.citation.volume 16 en_US
dc.contributor.authoreid aakeroy en_US
dc.contributor.authoreid desperj en_US


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