Energetics of the Inclusion of Organic Molecules by Rigidified Cone Calix[4]arenes in Carbon Tetrachloride

Supramolecular Chemistry

Volumn 13, Issue 2, 2001, Pages 379-386

  Arena, Giuseppe ^a   Contino, Annalinda ^a   Magrì, Antonio ^a   Sciotto, Domenico ^a   Arduini, Arturo ^b   Pochini, Andrea ^b   Secchi, Andrea ^b  

^a UNIVERSITY OF CATANIA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

Calixarenes; Calorimetry; CH interactions; Host guest chemistry; Inclusion compounds; Molecular recognition

Indexed keywords

EID: 0035564597     PISSN: 10610278     EISSN: None     Source Type: Journal    
DOI: 10.1080/10610270108027492     Document Type: Article

References (41)

1. (a) Sanemasa, I. and Akamine, Y. (1987). Bull. Chem. Soc. Jpn., 60, 2059;
2. (b) Fujiki, M., Deguchi, T. and Sanemasa, I. (1988). Bull. Chem. Soc. Jpn., 61, 1163;
3. (c) Vizitiu, D. and Thatcher, G. R. J. (1999). J. Org. Chem., 64, 6235;
4. (d) Huuskonen, J., Buston, J. E. H., Scotchmer, N. D. and Anderson, H. L. (1999). New J. Chem., 23, 1245.
5. (a) Fergurson, S. B., Seward, E. M., Diederich, F., Sanford, E. M., Chou, A., Inocencio-Szweda, P. and Knobler, C. B. (1988). J. Org. Chem., 53, 5595;
6. (b) Smithrud, D. B., Wyman, T. B. and Diederich, F. (1991). J. Am. Chem. Soc., 113, 5420;
7. (c) Petti, M. A., Shepodd, T. J., Barrans, R. E. and Dougherty, D. A. (1988). J. Am. Chem. Soc., 110, 6825.
8. (a) Danil de Namor, A. F., Wang, J., Gomez Orellana, I., Sueros Velarde, F. J. and Pacheko Tanaka, D. A. (1994). J. Incl. Phenom. Mol. Recognit. Chem., 19, 371;
9. (b) Danil de Namor, A. F., Garrido, Pardo, M. T., Pacheko Tanaka, D. A., Sueros Velarde, F. J. and Cardenas Garcia, J. D. (1993). J. Chem. Soc. Faraday Trans., 89, 2727.
10. Arena, G., Casnati, A., Contino, A., Sciotto, D. and Ungaro, R. (1997). Tetrahedron Lett., 38, 4685.
11. Arena, G., Contino, A., Gulino, F. G., Magrì, A., Sansone, F., Sciotto, D. and Ungaro, R. (1999). Tetrahedron Lett., 40, 1597.
12. Kobayashi, K., Asakawa, Y., Kikuchi, Y., Toi, H. and Aoyama, Y. (1993). J. Am. Chem. Soc., 115, 2648.
13. (a) Subramanian, S. and Zaworotko, M. J. (1994). Coord. Chem. Rev., 137, 357;
14. (b) Nishio, M., Umezawa, Y., Hirota, M. and Takeuchi, Y. (1995). Tetrahedron, 51, 8665;
15. (c) Malone, J. F., Murray, C. M., Charlton, M. H., Docherty, R. and Lavery, A. J. (1997). J. Chem. Soc., Faraday Trans, 3429;
16. (d) Steiner, T. and Desiraju, G. R. (1998). Chem. Commun., 891;
17. (e) Umezawa, Y., Tsuboyama, S., Honda, K., Uzawa, J. and Nishio, M. (1998). Bull. Chem. Soc. Jpn., 71, 1207;
18. (f) Umezawa, Y., Tsuboyama, S., Takahashi, H., Uzawa, J. and Nishio, M. (1999). Tetrahedron, 55, 10047.
19. Schneider, H.-J. (1991). Angew. Chem. Int. Ed. Engl., 30, 1417.
20. (a) Gutsche, C. D. (1989). Calixarenes, Monographs in Supramolecular Chemistry, Stoddart, J. F. Ed., The Royal Society of Chemistry, Cambridge;
21. (b) Gutsche, C. D. (1998). Calixarenes Revisited Monographs in Supramolecular Chemistry, Stoddart, J. F. Ed., The Royal Society of Chemistry, Cambridge;
22. (c) Andreetti, G. D. and Ugozzoli, F. (1991). In: Calixarenes, A Versatile Class of Macrocyclic Compounds, Vicens, J. and Böhmer, V. Eds., Kluwer Academic Publishers, Dordrecht and references therein; reference 1b, p. 169;
23. (d) Brouwer, E. B., Enright, G. D. and Ripmeester, J. A. (1997). J. Am. Chem. Soc., 119, 5404;
24. (e) Arduini, A., Nachtigall, F. F., Secchi, A., Pochini, A. and Ugozzoli, F. (2001). Supramol. Chem., in press.
25. Arduini, A., Fabbi, M., Mantovani, M., Mirone, L., Pochini, A., Secchi, A. and Ungaro, R. (1995). J. Org. Chem., 60, 1454.
26. Arduini, A., McGregor, W. M., Paganuzzi, D., Pochini, A., Secchi, A., Ugozzoli, F. and Ungaro, R. (1996). J. Chem. Soc., Perkin Trans 2, 839.
27. Arduini, A., McGregor, W. M., Pochini, A., Secchi, A., Ugozzoli, F. and Ungaro, R. (1996). J. Org. Chem., 61, 6881.
28. (a) Leggett, D. J. (1985). The Determination of Formation Constants: An Overview of Computational Methods for data Processing, In: Computational Methods for the Determination of Formation Constants; Leggett, D. J. Ed.; Plenum Press: New York, pp. 1-17;
29. (b) See e.g., Wilcox, C. S. (1991). In: Frontiers in Supramolecular Chemistry and Photochemistry, Schneider, H. J. and Durr, H. Eds., VCH, p. 123.
30. Sinanoglu, O. (1982). In: Molecular Interactions; Ratajczak, H. and Orville-Thomas, W. J. Eds., Wiley New York, 3, 283.
31. Williams, D. H. and Westwell, M. S. (1998). Chem. Soc. Rev., 27, 57.
32. (a) Calì, R., Rizzarelli, E., Sammartano, S. and Pettit, L. (1980). Thermochim. Acta, 35, 169;
33. (b) Arena, G., Gianguzza, A., Pellerito, L., Musumeci, S., Purrello, R. and Rizzarelli, E. (1990). J. Chem. Soc. Dalton Trans., p. 2603;
34. (c) Bonomo, R. P., Cucinotta, V., D'Alessandro, F., Impellizzeri, G., Maccarrone, G., Vecchio, G. and Rizzarelli, E. (1991). Inorg. Chem., 30, 2708.
35. (a) Anaud-Neu, F., Barboso, S., Berny, F., Casnati, A., Muzet, N., Pinalli, A., Ungaro, R., Schwing-Weill, M.-J. and Wipff, G. (1999). J. Chem. Soc. Perkin 2, 1727;
36. (b) Anaud-Neu, F., Barret, G., Fanni, S., Marrs, D., Mc Gregor, W., McKervey, M. A., Schwing-Weill, M.-J., Vetrogon, V. and Wechsler, S. (1995). J. Chem. Soc. Perkin 2, 453.
37. (a) Danil de Namor, A. F., Gil, E., Llosa Tanco, M. A., Pacheko Tanaka, D. A., Pulcha Salazar, L. E., Schulz, R. A. and Wang, J. (1995). J. Phys. Chem., 99, 16776;
38. (b) Danil de Namor, A. F., Gil, E., Llosa Tanco, M. A., Pacheko Tanaka, D. A., Pulcha Salazar, L. E., Schulz, R. A. and Wang, J. (1995). J. Phys. Chem., 99, 16781.
39. Zielenkiewicz, W., Lebedeva, N. S., Antina, E. V., Vygin, A. I. and Kaminski, M. (1998). J. Sol. Chem., 27, 879.
40. Izatt, R. M., Terry, R. E., Haymore, B. L., Hansen, L. D., Dalley, N. K., Avondet, A. G. and Christensen, J. J. (1976). J. Am. Chem. Soc., 98, 7620.
41. Eatough, E. A., Christensen, J. J. and Izatt, R. M. (1972). Thermochimica Acta, 3, 219.