Influence of the size of upper and lower rim substituents on the fluxional and complexation behaviour of calix[5]arenes

Tetrahedron Letters

Volumn 39, Issue 14, 1998, Pages 1965-1968

  Ferguson, George ^a   Notti, Anna ^b   Pappalardo, Sebastiano ^c   Parisi, Melchiorre F ^b   Spek, Anthony L ^d  

^a UNIVERSITY OF GUELPH   (Canada)

^b UNIVERSITY OF MESSINA   (Italy)

^c UNIVERSITY OF CATANIA   (Italy)

^d UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 0032473904     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00106-3     Document Type: Article

References (19)

1. 1. Gutsche, C. D. Calixarenes; Stoddart, J. F., Ed.; Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, 1989, Vol. 1. Calixarenes, a Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Ed.; Kluwer: Dordrecht, 1991. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745.
2. 1. Gutsche, C. D. Calixarenes; Stoddart, J. F., Ed.; Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, 1989, Vol. 1. Calixarenes, a Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Ed.; Kluwer: Dordrecht, 1991. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745.
3. 1. Gutsche, C. D. Calixarenes; Stoddart, J. F., Ed.; Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, 1989, Vol. 1. Calixarenes, a Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Ed.; Kluwer: Dordrecht, 1991. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745.
4. 2. Pappalardo, S.; Parisi, M. F. J. Org. Chem. 1996, 61, 8724-8725.
5. 3. Arnaud-Neu, F.; Fuangswasdi, S.; Notti, A.; Pappalardo, S.; Parisi, M. F. Angew. Chem., Int. Ed. Engl., in press.
6. 4. Gutsche, C. D.; Alam, I. Tetrahedron 1988, 44, 4689-4694. Markowitz, M. A.; Janout, V.; Castner, D. G.; Regen, S. L. J. Am. Chem. Soc. 1989, 111, 8192-8200.
7. 4. Gutsche, C. D.; Alam, I. Tetrahedron 1988, 44, 4689-4694. Markowitz, M. A.; Janout, V.; Castner, D. G.; Regen, S. L. J. Am. Chem. Soc. 1989, 111, 8192-8200.
8. 5. Stewart, D. R.; Gutsche, C. D. Org. Prep. Proced. Intl. 1993, 25, 137-139.
9. 6. Jakobi, R. A.; Böhmer, V.; Grüttner, C.; Kraft, D.; Vogt, W. New J. Chem. 1996, 20, 493-501.
10. 13C NMR spectroscopy, FAB (+) MS, and elemental analyses.
11. 8. (a) Iwamoto, K.; Araki, K.; Shinkai, S. Bull. Chem. Soc. Jpn. 1994, 67, 1499-1502.
12. (b) Stewart, D. R.; Krawiec, M.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. J. Am. Chem. Soc. 1995, 117, 586-601.
13. 12 Refinement of the modified data set then proceeded normally with anisotropic displacement parameters for all non-H atoms and H atoms treated and allowed for as riding atoms. The final R factor for the observed data is 0.067. Complete crystallographic details have been deposited with the Cambridge Crystallographic Data Centre and are also available from the authors in CIF format.
14. 10. Gabe, E. J.; Le Page, Y.; Charland, J. -P.; Lee, F. L.; White, P. S. J. Appl. Cryst. 1989, 22, 384-387.
15. 11. Sheldrick, G. M. SHELXL93, Program for the refinement of crystal structures, University of Göttingen, Germany, 1993.
16. 12. Spek, A. L. PLATON Molecular Geometry Program, University of Utrecht, Utrecht, Holland, November 1996 version.
17. 13. In the process of preparing this manuscript we became aware that similar results have also been found for p-H-calix[5]arene pentaketones. Bell, S. E. J.; Browne, J. K.; McKee, V.; McKervey, M. A.; Malone, J. F.; O'Leary, M.; Walker, A. J. Org. Chem., in press. We warmly thank Professor M. A. McKervey for providing us with a copy of his manuscript prior to publication.
18. 14. Barret, G.; McKervey, M. A.; Malone, J. F.; Walker, A.; Arnaud-Neu, F.; Guerra, L.; Schwing-Weill, M. -J.; Gusche, C. D.; Stewart, D. R. J. Chem. Soc. Perkin Trans. 2 1993, 1475-1479.
19. c = 388 K).