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Volumn 41, Issue 20, 2002, Pages 3793-3796

Solid-state and solution studies of a tetrameric capsule and its guests

Author keywords

Host guest systems; Hydrogen bonds; Molecular recognition; Self assembly; Supramolecular chemistry

Indexed keywords

CRYSTAL STRUCTURE; HYDROGEN BONDS; KETONES;

EID: 0037131498     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (27)

References (40)
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    • note
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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].
    • (1991) Proteins-Structure Function and Genetics , vol.11 , pp. 281-296
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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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    • Atwood, J.L.1    Barbour, L.J.2    Jerga, A.3
  • 39
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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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    • 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.
    • (1999) Chem. Commun. , pp. 2413-2414
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.