Hydrogen bonded homo- and heterodimers of tetra urea derivatives of calix[4]arenes

Tetrahedron

Volumn 52, Issue 25, 1996, Pages 8489-8496

  Mogck, Oliver ^a   Böhmer, Volker ^a   Vogt, Walter ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON; UREA DERIVATIVE;

ARTICLE; DIMERIZATION; DRUG CONFORMATION; DRUG SYNTHESIS; HYDROGEN BOND; KIDNEY CALYX; MACROMOLECULE; PRIORITY JOURNAL;

EID: 0002395534     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00404-8     Document Type: Article

References (21)

1. Lawrence, D. S., Jiang, T., Levett, M. Chem. Rev. 1995, 95, 2229-2260.
2. a) Ghadiri, M. R., Kobayashi, K., Granja,. J. R., Chadha, R. K., McRee, D. E. Angew. Chem 1995, 107, 76-78;
3. b) Cram., D. J., Choi, H.-J., Bryant, J. A., Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7748-7765;
4. c) Bonar-Law, R. P., Sanders, J. K. M. Tetrahedron Lett. 1993, 34, 1677-1680.
5. a) Branda, N., Grotzfeld, R. M., Valdes, C., Rebek, J. Jr. J. Am. Chem. Soc. 1995, 117, 85-88;
6. b) Valdes, C., Spitz, U. P., Toledo, L. M., Kubik, S. W., Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 12733-12745.
7. Etter, M., Urbanczyk-Lipkowska, Z., Zia-Ebrahimi, M., Panunto, T. W. J. Am. Chem. Soc. 1990, 112, 8415-8426.
8. Calix[4]arenes bearing ureafunctions at the upper rim were first prepared by D. N. Reinhoudt et al. and shown to complex anions: Scheerder, J., Engbersen, J. F. J., Reinhoudt, D. XXth International Symposium on Macrocyclic Chemistry, Jerusalem, July 1995. For calix[4]arenes and calix[6]arenes with urea functions at the lower rim see: a) Scheerder, J., Fochi, M., Engbersen, J. F. J., Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815-7820;
9. Calix[4]arenes bearing ureafunctions at the upper rim were first prepared by D. N. Reinhoudt et al. and shown to complex anions: Scheerder, J., Engbersen, J. F. J., Reinhoudt, D. XXth International Symposium on Macrocyclic Chemistry, Jerusalem, July 1995. For calix[4]arenes and calix[6]arenes with urea functions at the lower rim see: a) Scheerder, J., Fochi, M., Engbersen, J. F. J., Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815-7820;
10. b) Scheerder, J., Engbersen, J. F. J., Casnati, A., Ungaro, R., Reinhoudt, D. N. J. Org. Chem. 1995, 60, 6448-6454.
11. Jakobi, R. A., Böhmer, V., Grüttner, C., Kraft, D., Vogt, W. New J. Chem., in press.
12. Such a pinched cone conformation has been suggested for calix[4]arene with amide groups at the upper rim: Conner, M., Janout, V., Regen, S. L. J. Am. Chem. Soc. 1991, 113, 9670-9671.
13. a) Shimizu, K. D., Rebek, J., Jr. Proc. Nat. Acad. Sci., 1995, 92, 12403-12407;
14. b) Hamann, B. C., Shimizu, K. D., Rebek, J., Jr. submitted to Angew. Chem. (personal communication).
15. For a hydrogen bonded double calix[4]arene consisting of two different calix[4]arenes see: Koh, K., Araki, K., Shinkai, S. Tetrahedron Lett. 1994, 35, 8255-8258.
16. Both calix[4]arene moieties are mirror imaged (enantiomeric) conformers with the O=C-groups pointing in a clockwise or counterclockwise direction.
17. Timmermann, P., PhD Thesis, University of Enschede, The Netherlands.
18. 6 leads to a complete destruction of the dimer, which can also be achieved by the addition of a simple dialkyl or diaryl urea.
19. 1H NMR spectra with very broad signals are observed.
20. 4 due to the nonequivalence of A and B.
21. It is unclear from our results whether the signals around 3.5 ppm in the spectrum of 2b are caused by an included guest (compare ref. 8.).