Aakeröy, Christer B.Chopade, Prashant D.Quinn, Colette F.Desper, John2014-06-202014-06-202014-06-20http://hdl.handle.net/2097/17868A 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-USThis Rights Statement can be used for an Item that is in copyright. Using this statement implies that the organization making this Item available has determined that the Item is in copyright and either is the rights-holder, has obtained permission from the rights-holder(s) to make their Work(s) available, or makes the Item available under an exception or limitation to copyright (including Fair Use) that entitles it to make the Item available.Multimeric cavitand assemblyCavitandX-ray diffractionInfrared spectroscopyArticle (author version)