Binding of neutral substrates by calix[4]pyrroles

Journal of the American Chemical Society

Volumn 118, Issue 49, 1996, Pages 12471-12472

  Allen, William E ^a   Gale, Philip A ^a   Brown, Christopher T ^a   Lynch, Vincent M ^a   Sessler, Jonathan L ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; PYRROLE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; DRUG BINDING; DRUG STRUCTURE; MOLECULAR DYNAMICS;

EID: 0030469794     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9632217     Document Type: Article

References (43)

1. For reviews of neutral substrate binding, see:
2. (a) Weber, E.; Vogtle, F. In Comprehensive Supramolecitlar Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Elsevier Science Ltd.: Oxford, 1996; Vol. 2, pp 1-28 and references therein,
3. (b) Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993, 383-395.
4. For examples of alcohol recognition, see:
5. (a) Beer, P. D.; Gale, P. A.; Chen, Z.; Drew, M. G. B. Supramol. Chem. 1996, 7, 241-255.
6. (b) Huang, C.-Y.; Cabell, L. A.; Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2778-2792.
7. Sessler, J. L.; Mody, T. D.; Lynch, V. J. Am. Chem. Soc. 1993, 115, 3346-3347.
8. Cochran, J. E.; Parrott, T. J.; Whitlock, B. J.; Whitlock, H. W. J. Am. Chem. Soc. 1992, 114, 2269-2270.
9. (e) Bugge, K.-E.; Verboom, W.; Reinhoudt, D. N.; Harkema, S. Acta Crystallogr. 1992, C48, 1848-1851.
10. For examples of amide and peptide recognition, see:
11. (a) Ge, Y.; Lilienthal, R. R.; Smith, D. K. J. Am. Chem. Soc. 1996, 118, 3976-3977.
12. (b) Albert, J. S.; Goodman, M. S.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 1143-1144.
13. Torneiro, M.; Still, W. C. J. Am. Chem. Soc. 1995, 117, 5887-5888.
14. Nadin, A.; Derrer, S.; McGeary, R. P.; Goodman, J. M.; Raithby, P. R.; Holmes, A. B.; O'Hanlon, P. J.; Pearson, N. D. J. Am. Chem. Soc. 1995, 777, 9768-9769.
15. (e) Bisson, A. P.; Carver, F. J.; Hunter, C. A.; Waltho, J. P. J. Am. Chem. Soc. 1994, 776, 10292-10293.
16. (f) van Straaten-Nijenhuis, W. F.; van Doom, A. R.; Reichwein, A. M.; de Jong, F.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 2265-2271.
17. Substrate encapsulation can afford very stable complexes:
18. (a) Grotzfeld, R. M.; Branda, N.; Rebek, J., Jr. Science 1996, 277, 487-489.
19. (b) Eid, C. N., Jr.; Knobler, C. B.; Gronbeck, D. A.; Cram, D. J. J. Am. Chem. Soc. 1994, 116, 8506-8515.
20. (a) Jacoby, D.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. J. Chem. Soc., Chem. Commun. 1991, 790-792.
21. (b) Brown, W. H.; Hutchinson, B. J.; MacKinnon, M. H. Can. J. Chem. 1971, 49, 4017-4022.
22. Rothemund, P.; Gage, C. L. J. Am. Chem. Soc. 1955, 77, 3340-3342.
23. Dennstedt, M.; Zimmerman, J. Ber. Dtsch. Chem. Ges. 1887, 20, 850-857.
24. (e) Baeyer, A. Der. Dtsch. Chem. Ges. 1886, 19, 2184-2185.
25. (a) Gale, P. A.; Sessler, J. L.; Krai, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140-5141.
26. (b) Sessler, J. L.; Andrievsky, A.; Gale, P. A.; Lynch, V. Angew. Chem., Int. Ed. Engl. In press.
27. (a) Floriani, C. Chem. Commun. 1996, 1257-1263.
28. (b) von Maltzan, B. Angeu: Chem., Int. Ed. Engl. 1982, 21, 785-786.
29. Conformational rigidity is entropically favorable for a receptor which is designed to bind one particular substrate:
30. (a) Peterson, B. R.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1625-1628.
31. (b) Zimmerman, S. C.; Wu, W.; Zeng, Z. J. Am. Chem. Soc. 1991, 113, 196-201.
32. eq for the attached N atom.
33. A similar structural motif has been observed in the adduct formed between an oxidized porphyrin and water: Golder, A. J.; Milgrom, L. R.; Nolan, K. B.; Povey, D. C. J. Chem. Soc., Chem. Commun. 1989, 1751-1753.
34. w = 0.0952, GOF = 1.061 for 291 parameters. The NH protons of 1.2(DMF) were obtained from a ΔF map and refined with isotropic thermal parameters.
35. (a) Pappalardo, S.; Petringa, A.; Parisi, M. F.; Ferguson, G. Tetrahedron Lett. 1996, 37, 3907-3910.
36. (b) No, K.; Park, Y. J.; Kim, K. H.; Shin, J. M. Bull. Kor. Chem. Soc. 1996, 17, 447-452.
37. Compound 2 is a new substance. See the Supporting Information for synthetic experimental and characterization data.
38. lattice were obtained from a ΔF map and refined with isotropic thermal parameters.
39. Hynes, M. J. J. Chem. Soc., Dalton Trans. 1993, 311-312.
40. 2 may also be formed: Lenkinski, R. L.; Elgavish, G. A.; Reuben, J. J. Magn. Resort. 1978, 32, 367-376.
41. Kamlet, M. J.; Abboud, J.-L. M.: Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887.
42. 6.
43. A priori, tetramethylurea was expected to be the most strongly bound of the amides based upon electronic considerations (see ref 17).