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note
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22
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0034600293
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The symbol "⊂" signifies "is encapsulated by". In this context the term "head-to-tail" reflects a "heterorecognition" of the hydrogen bonding groups (sulfamide to glycoluril) rather than a "homorecognition" (e.g. glycoluril to glycoluril). A structurally similar version of the monomers 1 and 2 was reported as a component in a library of heteromeric capsules studied by mass spectrometry: F. Hof, C. Nuckolls, J. Rebek, Jr., J. Am. Chem. Soc. 2000, 122, 4251-4252. The solution-phase and solid-state assembly of this monomer were not reported.
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All cavity and guest volume measurements were calculated from crystal structures using the GRASP program (A. Nicholls, K. A. Sharp, B. Honig, Proteins-Structure Function and Genetics 1991, 11, 281-296) following a procedure described in reference [17].
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38
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0037117632
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The multiple solvent guests are internally ordered in the solid state by hydrogen bonds formed with the interior of their hexameric hydrogen-bonded capsule host: J. L. Atwood, L. J. Barbour, A. Jerga, Proc. Natl. Acad. Sci. USA 2002, 99, 4837-4841.
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The formation of four similar hydrogen bonds to a single carbonyl group is an unusual demonstration that the purely electrostatic nature of the hydrogen bond is often more important than the directionality imposed by the location of the lone pairs. In a rare solid-state example of a ketone carbonyl group accepting two intermolecular hydrogen bonds, the lone pairs of the oxygen atom were perfectly aligned with the hydrogen-bond donors: O. Saied, M. Simard, J. D. Wuest, J. Org. Chem. 1998, 63, 3756-3757. In another solid-state example, a calix[4]pyrrole donates four long hydrogen bonds to a solvent ketone: L. Bonomo, E. Solari, G. Toraman, R. Scopelliti, M. Latronico, C. Floriani, Chem. Commun. 1999, 2413-2414.
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0002746602
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The formation of four similar hydrogen bonds to a single carbonyl group is an unusual demonstration that the purely electrostatic nature of the hydrogen bond is often more important than the directionality imposed by the location of the lone pairs. In a rare solid-state example of a ketone carbonyl group accepting two intermolecular hydrogen bonds, the lone pairs of the oxygen atom were perfectly aligned with the hydrogen-bond donors: O. Saied, M. Simard, J. D. Wuest, J. Org. Chem. 1998, 63, 3756-3757. In another solid-state example, a calix[4]pyrrole donates four long hydrogen bonds to a solvent ketone: L. Bonomo, E. Solari, G. Toraman, R. Scopelliti, M. Latronico, C. Floriani, Chem. Commun. 1999, 2413-2414.
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