The binding behavior of cyclodextrins toward a nitroxide spin probe in the presence of different alcohols as studied by EPR

Journal of Physical Chemistry A

Volumn 112, Issue 37, 2008, Pages 8706-8714

  Franchi, Paola ^a   Pedulli, Gian Franco ^a   Lucarini, Marco ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLODEXTRINS;

ACTIVATION PARAMETERS; BINDING BEHAVIORS; INCLUSION COMPLEXES; NITROXIDE; SPIN PROBES; STABILITY CONSTANTS;

THERMODYNAMIC STABILITY;

ALCOHOL DERIVATIVE; CYCLODEXTRIN; NITROGEN OXIDE; WATER;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON SPIN RESONANCE; HYDROPHOBICITY; METHODOLOGY; MOLECULAR PROBE; PARTICLE SIZE; REPRODUCIBILITY; SPIN LABELING; STEREOISOMERISM; THERMODYNAMICS;

ALCOHOLS; BINDING SITES; CYCLODEXTRINS; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROPHOBICITY; MOLECULAR PROBES; MOLECULAR STRUCTURE; NITROGEN OXIDES; PARTICLE SIZE; REPRODUCIBILITY OF RESULTS; SPIN LABELS; STEREOISOMERISM; THERMODYNAMICS; WATER;

EID: 53149136648     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp8051642     Document Type: Article

References (55)

1. Szejtli, J. Cyclodextrins and Their Inclusion Complexes; Akademiai Kiado: Budapest, 1982.
2. Wenz, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 803-822.
3. Horsky, J.; Pitha, J. J. Pharm. Sci. 1996, 96-100.
4. Connors, K. A. Chem. Rev. 1997, 97, 1325-1357.
5. Schneider, H. J.; Hacket, F.; Rüdiger, V. Chem. Rev. 1998, 98, 1755-1785.
6. Mulski, M.; Connors, K. A. Supramol. Chem. 1995, 271-278.
7. Allenmark, S. Chromatographic Enantioseparation: Methods and Applications; Ellis Horwood: New York, 1991.
8. Sbai, M.; Ait Lyazidi, A.; Lerner, D. A.; del Castello, B.; Martin, M. A. Anal. Chim. Acta 1995, 303, 47-55.
9. Villalonga, R.; Cao, R.; Fragoso, A. Chem. Rev. 2007, 107, 3088-3116.
10. Uekama, K.; Hirayama, F.; Tetsumi, I. Chem. Rev. 1998, 98, 2045-2076.
11. Fromming, K. H.; Szejtli, J. Cyclodextrins in Pharmacy; Kluwer Academic Publishers: Dordrecht, 1994.
12. Loftsson, T.; Brewster, M. J. Pharm. Sci. 1996, 85, 1017-1025.
13. Stella, V. J.; Rayewsky, R. A.; Zia, V. Pharm. Res. 2001, 18, 667-673.
14. Loftsson, T.; Jarvinen, T. Pharm. Res. 1998, 15, 1696-1701.
15. Nelson, G.; Patonay, G.; Warner, I. M. J. Inclusion Phenom. 1988, 6, 277-289.
16. Muñoz de la Peña, A.; Ndou, T. T.; Zung, J. B.; Greene, K. L.; Live, D. H.; Warner, I. M. J. Am. Chem. Soc. 1991, 113, 1572-1577.
17. Zung, J. B.; Muñoz de la Peña, A.; Ndou, T. T.; Warner, I. M. J. Phys. Chem. 1991, 95, 6701-6706.
18. Elliott, N. B.; Ndou, T. T.; Warner, I. M. J. Inclusion Phenom. Mol. Recognit. Chem. 1993, 16, 99-1031.
19. Schuette, J.; Will, Y.; Agbaria, R.; Warner, I. Appl. Spectrosc. 1994, 48, 581-586.
20. Hamay, S. J. Phys. Chem. 1989, 93, 2074-2078.
21. Schuette, J.; Ndou, T. T.; Muñoz de la Peña, A.; Mukundan, S.; Warner, I. J. Am. Chem. Soc. 1993, 115, 292-298.
22. Liao, Y.; Bohne, C. J. Phys. Chem. 1996, 100, 734-743.
23. Von Stam, J.; De Feiter, S.; De Schryver, F. C.; Evans, C. H. J. Phys. Chem. 1996, 100, 19959-19966.
24. Evans, C. H.; Partika, M.; van Stam, J. J. Inclusion Phenom. Macrocyclic Chem. 2000, 38, 381-396.
25. Partika, M.; Boo, H. A.; Evans, C. H. J. Photochem. Photobiol, A 2001, 140, 61-14.
26. Ma, L.; Tang, B.; Chu, C. Anal. Chim. Acta 2002, 469, 273-283.
27. Lucarini, M.; Luppi, B.; Pedulli, G. F.; Roberts, B. P. Chem.-Eur. J. 1999, 7, 1012-2048-1012-2054.
28. Lucarini, M.; Roberts, B. P. Chem. Commun. 1996, 1577-1578.
29. Franchi, P.; Lucarini, M.; Pedulli, G. F.; Sciotto, D. Angew. Chem., Int. Ed. 2000, 39, 263-266.
30. Brigati, G.; Franchi, P.; Lucarini, M.; Pedulli, G. F.; Valgimigli, L. Res. Chem. Intermed. 2002, 28, 131-141.
31. Franchi, P.; Lucarini, M.; Pedulli, G. F. Angew. Chem., Int. Ed. 2003, 42, 1842-1845.
32. Franchi, P.; Lucarini, M.; Mezzina, E.; Pedulli, G. F. J. Am. Chem. Soc. 2004, 126, 4343-4354.
33. Franchi, P.; Lucarini, M.; Pedulli, G. F.; Pengo, P.; Scrimin, P.; Pasquato, L. J. Am. Chem. Soc. 2004, 126, 9326-9329.
34. Franchi, P.; Lucarini, M.; Pedulli, G. F. Curr. Org. Chem. 2004, 8, 1831-1849.
35. Opallo, M.; Kobayashi, N.; Osa, T. J. J. Inclusion Phenom. Mol. Recognit. Chem. 1988, 7, 413-442.
36. Liu, Y.; Zhao, Y.; Zhang, H.; Fan, Z.; Wen, G.; Ding, F. J. Phys. Chem. B 2004, 108, 8836-8843.
37. Matsui, Y.; Mochida, K. Bull. Chem. Soc. Jpn. 1979, 52, 2808-2814.
38. Inoue, Y.; Rekharsky, M. Chem. Rev. 1998, 98, 1875-1917.
39. Liu, Y.; Yang, E. C.; Yang, Y. W.; Zhang, Z. F.; Fan, Z.; Ding, F.; Cao, R. J. Org. Chem. 2004, 69, 173-180.
40. Rekharsky, M. V.; Schwarz, F. P.; Tawari, Y. B.; Goldberg, R. N. J. Phys. Chem. 1994, 98, 10282-10286.
41. 2(R)).
42. Inoue, Y.; Rekharsky, M. J. Am. Chem. Soc. 2000, 122, 4418-4435.
43. 0 for alcohols 9-11 and 14 were calculated by means of ChemDraw 4.5 software. All of the other values have been taken from the literature: Leo, A.; Hausch, C.; Elkins, D. Chem. Rev. 1971, 71, 525.
44. 2 = 0.998.
45. Barone, G.; Castronuovo, G.; Del Vecchio, P.; Elia, V.; Muscetta, M. J. Chem. Soc., Faraday Trans. 1986, 82, 2089-2101.
46. Pathonay, G.; Fowler, K.; Shapira, A.; Nelson, J.; Warner, I. M. J. Inclusion Phenom. 1987, 5, 717-723.
47. Nishikawa, S.; Yamaguchi, K. Bull. Chem. Soc. Jpn. 1996, 69, 2465-2468.
48. Nishikawa, S. Bull. Chem. Soc. Jpn. 1997, 70, 1003-1007.
49. (a) Nishikawa, S.; Ugawa, T.; Fukahori, T. J. Phys. Chem. B 2001, 105, 7594-7597.
50. (b) Fukahori, T.; Nishikawa, S.; Yamaguchi, K. Bull. Chem. Soc. Jpn. 2004, 77, 2193-2198.
51. (a) Nishikawa, S.; Ugawa, T. J. Phys. Chem. A 2000, 704, 2914-2920.
52. (b) Nishikawa, S.; Kondo, M. J. Phys. Chem. B 2007, 111, 13451-13454.
53. (a) Inoue, Y.; Takehiko, W. Advances in Supramolecular Chemistry; JAI Press Inc.: Greenwich, 1997; Vol. 4, pp 55-96.
54. (b) Nakashima, H.; Yoshido, N. Org. Lett. 2006, 22, 4997-5001.
55. diss‡ are related to the change in randomness on passing from reactants or complex, respectively, to the transition state. In general, the following four terms should contribute to the activation entropy: (a) the freezing of motional degrees of freedom for the guest molecule, (b) the desolvation around the guest molecule and the reorganization of solvent water, (c) the release of water molecules from the CD cavity, and (d) any conformational changes of the CD torus. While the first term will be negative, the other ones are expected to contribute positively to the activation entropy. In the presence of alcohol, the picture is even more complicated, because the inclusion and the release of alcohol molecules by CD can significantly modify this picture. For this reason, we preferred to omit any detailed discussion on the activation entropies.