New cucurbituril homologues: Syntheses, isolation, characterization, and X-ray crystal structures of cucurbit[n]uril (n = 5, 7, and 8)

Journal of the American Chemical Society

Volumn 122, Issue 3, 2000, Pages 540-541

  Kim, Jaheon ^a   Jung, In Sun ^a   Kim, Soo Young ^a   Lee, Eunsung ^a   Kang, Jin Koo ^a   Sakamoto, Shigeru ^b   Yamaguchi, Kentaro ^b   Kim, Kimoon ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CUCURBITURIL; FORMALDEHYDE; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0034716334     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993376p     Document Type: Article

References (28)

1. Reviews on cucurbituril: (a) Mock, W. L. Top. Curr. Chem. 1995, 175, 1. (b) Cintas, P. J. Incl. Phenom. Mol. Reco. Chem. 1994, 17, 205. (c) Mock, W. L. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Oxford, 1996; Vol. 2, 477.
2. Reviews on cucurbituril: (a) Mock, W. L. Top. Curr. Chem. 1995, 175, 1. (b) Cintas, P. J. Incl. Phenom. Mol. Reco. Chem. 1994, 17, 205. (c) Mock, W. L. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Oxford, 1996; Vol. 2, 477.
3. Reviews on cucurbituril: (a) Mock, W. L. Top. Curr. Chem. 1995, 175, 1. (b) Cintas, P. J. Incl. Phenom. Mol. Reco. Chem. 1994, 17, 205. (c) Mock, W. L. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Oxford, 1996; Vol. 2, 477.
4. (a) Behrend, R.; Meyer, E.; Rusche, F. Liebigs Ann. Chem. 1905, 339, 1.
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6. (a) Mock, W. L.; Shih, N.-Y. J. Org. Chem. 1983, 48, 3618.
7. (b) Mock, W. L.; Shih, N.-Y. J. Org. Chem. 1986, 51, 4440.
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9. Mock, W. L.; Shih, N.-Y. J. Am. Chem. Soc. 1989, 111, 2697.
10. Mock, W. L.; Irra, T. A.; Wepsiec, J. P.; Manimaran, T. L. J. Org. Chem. 1983, 48, 3619.
11. (a) Jeon, Y.-M.; Kim, J.; Whang, D.; Kim, K. J. Am. Chem. Soc. 1996, 118, 9790.
12. (b) Whang, D.; Heo, J.; Park, J. H.; Kim, K. Angew. Chem., Int. Ed. 1998, 37, 78.
13. (a) Jeon, Y.-M.; Whang, D.; Kim, J.; Kim, K. Chem. Lett. 1996, 503.
14. (b) Whang, D.; Jeon, Y.-M.; Heo, J.; Kim, K. J. Am. Chem. Soc. 1996, 118, 11333.
15. (c) Whang, D.; Kim, K. J. Am. Chem. Soc. 1997, 119, 451.
16. Whang, D.; Heo, J.; Kim, C.-A.; Kim, K. J. Chem. Soc., Chem. Commun. 1997, 2361.
17. (e) Whang, D.; Park, K.-M.; Heo, J.; Kim, K. J. Am. Chem. Soc. 1998, 120, 4899.
18. (f) Roh, S.-G.; Park, K.-M.; Park, G.-J.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. Engl. 1999, 38, 638. Polyrotaxanes based on organic polymers and CB[6] have also been reported recently.
19. (g) Meschke, C.; Buschmann, H.-J.; Schollmeyer, E. Polymer 1999, 40, 945.
20. (h) Tuncel, D.; Steinke, H. G. Chem. Commun. 1999, 1509.
21. (a) Buschmann, H.-J. Biol. Abwasserreinig. 1997, 9, 101.
22. (b) Karcher, S.; Kornmüller, A.; Jekel, M. Acta Hydrochim. Hydrobiol. 1999, 27, 38.
23. A cyclic pentamer has been obtained from the reaction of dimethylglycoluril and formaldehyde: Flinn, A.; Hough, G. C.; Stoddart, J. F. Williams, D. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1475.
24. +. Satisfactory elemental analyses were obtained for all the new compounds.
25. 2(all data) = 0.290, GOF = 1.042. In the crystal structure of CB[5], two water molecules are encapsulated in the cavity of the receptor. A disordered THF molecule is found inside the cavity of CB[7] and disordered water molecules and/or hydronium ions in the cavity of CB[8]. A detailed description of the structures will be published elsewhere.
26. The hydrochloride salt of 2,6-bis(4,5-dihydro-1H-imidazol-2-yl)-naphthalene (1) was synthesized from 2,6-dicarboxynaphthalene and ethylenediamine according to a literature method (Kraft, A. J. Chem. Soc., Perkin Trans, 1 1999, 705).
27. 2(all data) = 0.311, GOF = 1.019.
28. The 1:2 inclusion complex 2 presents a new type of stereoisomerism.