Guest-induced assembly of tetracarboxyl-cavitand and tetra(3-pyridyl)-cavitand into a heterodimeric capsule via hydrogen bonds and CH - halogen and/or CH - π interaction: Control of the orientation of the encapsulated guest

Journal of the American Chemical Society

Volumn 125, Issue 35, 2003, Pages 10615-10624

  Kobayashi, Kenji ^a   Ishii, Kei ^a   Sakamoto, Shigeru ^b   Shirasaka, Toshiaki ^c   Yamaguchi, Kentaro ^b  

^a SHIZUOKA UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

^c UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; SINGLE CRYSTALS; X RAY ANALYSIS;

HETERODIMERIC CAPSULES;

AROMATIC HYDROCARBONS;

BENZENE DERIVATIVE; CARBOXYL GROUP; HALOGEN;

ANALYTIC METHOD; ARTICLE; COVALENT BOND; DIMERIZATION; DRUG DELIVERY SYSTEM; ENCAPSULATION; HYDROGEN BOND; PROTEIN ASSEMBLY; PROTON NUCLEAR MAGNETIC RESONANCE; THERMODYNAMICS; X RAY DIFFRACTION;

EID: 0042856768     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035337q     Document Type: Article

References (66)

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57. CSI-MS is a method for the low-temperature measurement of ESI-MS, wherein the ion source temperature is the range from -20 °C to room temperature. The CSI-MS is a very powerful method for the detection of supramolecular aggregates, and the molecular mass observed fairly reflects the structure in solution. (a) Sakamoto, S.; Fujita, M.; Kim, K.; Yamaguchi, K. Tetrahedron 2000, 56, 955-964. (b) Sakamoto, S.; Yamaguchi, K. Angew. Chem., Int. Ed. 2003, 42, 905-908 and references therein.
58. CSI-MS is a method for the low-temperature measurement of ESI-MS, wherein the ion source temperature is the range from -20 °C to room temperature. The CSI-MS is a very powerful method for the detection of supramolecular aggregates, and the molecular mass observed fairly reflects the structure in solution. (a) Sakamoto, S.; Fujita, M.; Kim, K.; Yamaguchi, K. Tetrahedron 2000, 56, 955-964. (b) Sakamoto, S.; Yamaguchi, K. Angew. Chem., Int. Ed. 2003, 42, 905-908 and references therein.
59. 2H⋯N hydrogen bonds are 2.28, 2.31, 2.42, and 2.54 Å for 1-iodo-4-methoxybenzene@(1b·2b) and 2.24, 2.39. 2.44, and 2.45 Å forp-xylene@(1b·2b). Although the final level has not yet been reached, we think the data obtained here are significant enough to demonstrate the supramolecular structure of guest@(1b·2b).
60. Godinez, C. E.; Zepeda, G.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2002, 124, 4701-4707.
61. (a) Eaton, D. F.; Anderson, A. G.; Tam, W.; Wang, Y. J. Am. Chem. Soc. 1987, 109, 1886-1888.
62. (b) Hoss, R.; König, O.; Kramer-Hoss, V.; Berger, U.; Rogin, P.; Hulliger, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1664-1666.
63. (c) Bénard, S.; Yu, P.; Audière, J. P.; Rivière, E. ; Clément, R.; Guilhem, J.; Tchertanov, L.; Nakatani, K. J. Am. Chem. Soc. 2000, 122, 9444-9454.
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