The quest for chain-link hydrogen-bonded capsules: Self-assembly of C-methyl calix[4]resorcinarene with 1,2-bis(5′-pyrimidyl)ethyne

Crystal Growth and Design

Volumn 4, Issue 2, 2004, Pages 235-239

  Georgiev, Ivan ^a   Bosch, Eric ^a   Barnes, Charles L ^b   Draganjac, Mark ^c  

^a MISSOURI STATE UNIVERSITY   (United States)

^b UNIVERSITY OF MISSOURI   (United States)

^c ARKANSAS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE;

ARTICLE; CHEMICAL STRUCTURE; CROSS LINKING; HYDROGEN BOND; LIGAND BINDING;

EID: 1642445335     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg034108c     Document Type: Article

References (25)

1. (a) See, for example, Calixarenes in Action; Mandolini, L., Ungaro, R., Eds.; Imperial College Press: London, 2000.
2. (b) Shivanyuk, A.; Rebek, J., Jr. Chem. Commun. 2002, 2326.
3. (c) Alarjarin, M.; Pastor, A.; Orenes, R.-A.; Steed, J. W. J. Org. Chem. 2002, 67, 7091.
4. (d) Zadmard, R.; Schrader, T.; Grawe, T.; Kraft, A. Org. Lett. 2002, 4, 1687.
5. For a review see Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663.
6. MacGillivray, L. R.; Atwood, J. L. Chem. Commun. 1999, 181.
7. (b) MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. CrystEngComm 1999, 1.
8. (a) MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. Chem. Commun. 2001, 1034.
9. (b) MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. CrystEngComm 1999, 1.
10. (c) MacGillivray, L. R.; Papaefstathiou, G. S.; Reid, J. L.; Ripmeester, J. A. Cryst. Growth Des. 2001, 1, 373.
11. (d) MacGillivray, L. R.; Diamente, P. R.; Reid, J. L.; Ripmeester, J. A. Chem. Commun. 2000, 359.
12. (e) Frisic, T.; MacGillivray, L. R. J. Organomet. Chem. 2003, 666, 43.
13. (a) Ma, B. Q.; Zhang, Y.; Coppens, P. CrystEngComm 2001, 20, 1.
14. (b) Ma, B. Q.; Zhang, Y.; Coppens, P. Cryst. Growth Des. 2001, 1, 271.
15. (c) Ma, B. Q.; Coppens, P. Chem. Commun. 2003, 5412.
16. (d) Ma, B. Q.; Coppens, P. Chem. Commun. 2003, 504.
17. Cave, G. W. V.; Hardie, M. J.; Roberts, B. A.; Raston, C. L. Eur. J. Org. Chem. 2001, 3227.
18. Georgiev, I.; Bosch, E.; Barnes, C. L. J. Supramol. Chem., 2001, 1, 153.
19. Sheldrick, G. M. SHELXS-97, Crystal Structure Solution; University of Göttingen, Germany, 1997.
20. Sheldrick, G. M. SHELXL-97, Crystal Structure Refinement; University of Göttingen, Germany, 1997.
21. Drawings prepared using the program X-seed, L. Barbour, University of Missouri, Columbia, MO 65211.
22. These values are typical for these intramolecular hydrogen bonds. See for example refs 3-5.
23. Moorthy, J. N.; Natarajan, R.; Venugopalan, P. Angew. Chem., Int. Ed. 2002, 41, 3417.
24. For a review see Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647.
25. For an elegant example of this strategy based on hydrogen bonding see MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. J. Am. Chem. Soc. 2000, 112, 7817.