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Volumn 51, Issue 5-6, 2011, Pages 559-577

Deep inside cucurbiturils: Physical properties and volumes of their inner cavity determine the hydrophobic driving force for host-guest complexation

Author keywords

Cucurbiturils; Host guest systems; Macrocycles; Packing coefficients; Solvatochromic probes; Supramolecular chemistry

Indexed keywords


EID: 79957562110     PISSN: 00212148     EISSN: 18695868     Source Type: Journal    
DOI: 10.1002/ijch.201100044     Document Type: Review
Times cited : (314)

References (186)
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    • CB5 has a much higher tendency to include anions than other CBs, at least in the solid state. This tendency is not understood. While in the case of cyclodextrins dispersion interactions are considered to be largest (cf. V. Rüdiger, A. Eliseev, S. Simova, H. J. Schneider, M. J. Blandamer, P. M. Cullis, A. J. Meyer, J. Chem. Soc. Perkin Trans. 2 1996, 2119-2123
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    • and ref. [38] for the smallest homologue (α-cyclodextrin), this reason appears to be unlikely for CB5, owing to the low polarizability of CBs in general. Alternative reasons could include i a particularly high driving force for the removal of the two very-high-energy water molecules from the cavity (see Section 5), ii favorable ion pairing with cations docked to the upper rim, and/or iii geometrically more favorable electrostatic interactions of the anions with the electron-deficient carbonyl carbons. The latter are well known to drive anion binding to the structurally related macrocycles termed hemicucurbit[6]uril, cf.
    • and ref. [38]) for the smallest homologue (α-cyclodextrin), this reason appears to be unlikely for CB5, owing to the low polarizability of CBs in general. Alternative reasons could include i) a particularly high driving force for the removal of the two very-high-energy water molecules from the cavity (see Section 5), ii) favorable ion pairing with cations docked to the upper rim, and/or iii) geometrically more favorable electrostatic interactions of the anions with the electron-deficient carbonyl carbons. The latter are well known to drive anion binding to the structurally related macrocycles termed hemicucurbit[6]uril, cf. H. J. Buschmann, E. Cleve, E. Schollmeyer, Inorg. Chem. Commun. 2005, 8, 125-127,
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    • -1 for CB5. For CB6, this value has not yet been reached for neutral guests (Table 3), which may be due to the use of salt-containing solutions (see above), while for CB5 no absolute binding constants with neutral guests have yet been reported.
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    • The fact that CB8 forms numerous 2 :1 complexes with aromatic molecules (cf., for example, refs. [139] and [140]) provides no indication for significant dispersion interactions either, because one of the included guests (e.g., methylviologen) is always held in place by (two) ion-dipole interactions, while the inclusion of a second, electron-rich aromatic neutral guest (e.g., 2,6-dihydroxynaphthalene or 1,4-dihydroxybenzene) is, arguably, driven by dispersion and charge-transfer interactions with the first guest rather than with the cavity, in addition to hydrophobic interactions, see also
    • The fact that CB8 forms numerous 2 :1 complexes with aromatic molecules (cf., for example, refs. [139] and [140]) provides no indication for significant dispersion interactions either, because one of the included guests (e.g., methylviologen) is always held in place by (two) ion-dipole interactions, while the inclusion of a second, electron-rich aromatic neutral guest (e.g., 2,6-dihydroxynaphthalene or 1,4-dihydroxybenzene) is, arguably, driven by dispersion and charge-transfer interactions with the first guest rather than with the cavity, in addition to hydrophobic interactions, see also U. Rauwald, F. Biedermann, S. Deroo, C. V. Robinson, O. A. Scherman, J. Phys. Chem. B 2010, 114, 8606-8615.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.