Site-specific interaction between 2-dibenzofuran carboxylate and β- And γ-cyclodextrins determined by intermolecular NOE and molecular modeling

Journal of Physical Chemistry B

Volumn 108, Issue 37, 2004, Pages 14154-14162

  González Gaitano, Gustavo ^a   Sainz Rozas, Pablo R ^a   Isasi, José Ramón ^a   Guerrero Martínez, Andrés ^b   Tardajos, Gloria ^b  

^a UNIVERSITY OF NAVARRA   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; BOUNDARY CONDITIONS; COMPUTATIONAL GEOMETRY; COMPUTER SIMULATION; CONCENTRATION (PROCESS); FLUORESCENCE; MATHEMATICAL MODELS; MOLECULAR DYNAMICS; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONS; SOLVENTS; STOICHIOMETRY;

CYCLODEXTRINS (CD); DIBENZOFURAN (DBF); GLYCOSIDIC BONDS; MOLECULAR MODELING;

CARBOXYLIC ACIDS;

EID: 4644310946     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0484231     Document Type: Article

References (31)

1. Szejtli, J. Cyclodextrins and Their Inclusion Complexes; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1988.
2. (b) Duchene, D. Cyclodextrins and Their Industrial Uses; Editions de Santé: Paris, 1987.
3. Duchene, D. New Trends in Cyclodextrins and Derivatives; Editions de Santé: Paris, 1991.
4. Hedges, A. R. Chem. Rev. 1998, 98, 2035.
5. Connors, K. A. Chem. Rev. 1997, 97, 1325.
6. (b) Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 95, 1875.
7. Sainz-Rozas, P. R.; Isasi, J. R.; Sanchez, M.; Tardajos, G.; González-Gaitano, G. J. Phys. Chem. A. 2004, 108, 392.
8. Schneider, H. J.; Hacket, F.; Rüdiger, V. Chem. Rev. 1998, 98, 1755.
9. Neuhaus, D.; Williamsom, M. P. The Nuclear Overhauser Effect in Structural and Conformational Analysis; VCH: New York, 1989.
10. Bax, A.; Davis, D. G. J. Magn. Reson. 1985, 63, 207.
11. MestRe-C, version 3.5.1; Departamento de Química Orgánica, Universidad de Santiago de Compostela: Santiago de Compostela, Spain, 2003.
12. Ämmälahti, E.; Bardet, M.; Molko, D.; Cadet, J. J. Magn. Reson. A. 1996, 122, 230.
13. Insight II, version 2000: Accelrys Inc.: San Diego, CA, 2000.
14. Weiner, S. J.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comput. Chem. 1986, 7, 230.
15. Homans, S. W. Biochemistry 1990, 29, 9110.
16. Connors, K. A. Binding Constants. The Measurement of Molecular Complex Stability; John Wiley " Sons: New York, 1987; pp 189-192.
17. For a review of binding constants by NMR spectroscopy, see Fielding, L. Tetrahedron 2000, 56, 6151 and references therein.
18. González-Gaitano, G.; Guerrero-Martínez, A.; Núñez-Barriocanal, J. L.; Tardajos, G. J. Phys. Chem. B. 2002, 106, 6096.
19. See, for example: Gelb, R. I.; Schwartz, L. M.; Laufer, D. A. J. Am. Chem. Soc. 1978, 100, 5875. Salvatierra, D.; Díez, C.; Jaime, C. J. Inclusion Phenom. Macrocyclic Chem. 1997, 27, 215. Al-Soufi, W.; Ramos Cabrer, P.; Jover, A.; Budal, R. M.; Vázquez Tato, J. Steroids 2003, 68, 43.
20. See, for example: Gelb, R. I.; Schwartz, L. M.; Laufer, D. A. J. Am. Chem. Soc. 1978, 100, 5875. Salvatierra, D.; Díez, C.; Jaime, C. J. Inclusion Phenom. Macrocyclic Chem. 1997, 27, 215. Al-Soufi, W.; Ramos Cabrer, P.; Jover, A.; Budal, R. M.; Vázquez Tato, J. Steroids 2003, 68, 43.
21. See, for example: Gelb, R. I.; Schwartz, L. M.; Laufer, D. A. J. Am. Chem. Soc. 1978, 100, 5875. Salvatierra, D.; Díez, C.; Jaime, C. J. Inclusion Phenom. Macrocyclic Chem. 1997, 27, 215. Al-Soufi, W.; Ramos Cabrer, P.; Jover, A.; Budal, R. M.; Vázquez Tato, J. Steroids 2003, 68, 43.
22. MATLAB, version 5.2, The MathWorks, Inc.: Natick, MA, 1998.
23. Funasaki, N.; Ishikawa, S.; Neya, S. J. Phys. Chem. B 2002, 106, 6431.
24. Salvatierra, D.; Jaime, C.; Virgili, A.; Sánchez-Ferrando, F. J. Org. Chem. 1996, 61, 9578.
25. Salvatierra, D.; Sánchez-Ruiz, X.; Garduño, R.; Cervelló, E.; Jaime, C.; Virgili, A.; Sánchez-Ferrando, F. Tetrahedron 2000, 56, 3035.
26. Zubiaur, M.; Jaime, C. J. Org. Chem. 2000, 65, 8139.
27. Kim, H.; Jeong, K.; Lee, S.; Jung, S. Bull. Korean Chem. Soc. 2003, 24, 95.
28. Dodziuk, H.; Lukin, O. Chem. Phys. Lett. 2000, 327, 18.
29. Rodríguez, P.; Sánchez, M.; Isasi, J. R.; González-Gaitano, G. Appl. Spectrosc. 2002, 56, 1490.
30. - group is not affected by the complexation.
31. Minn, F. L.; Pinion, J. P.; Filipescu, N. J. Phys. Chem. 1971, 75, 1794.