Probing binding-mode diversity in guanidinium-oxoanion host-guest systems

ChemPhysChem

Volumn 6, Issue 6, 2005, Pages 1181-1186

  Haj Zaroubi, Manal ^a   Schmidtchen, Franz P ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Calorimetry; Host guest systems; Ligand design; Molecular recognition; Thermodynamics

Indexed keywords

BINDING ENERGY; CALORIMETERS; CALORIMETRY; CATALYSIS; COMPLEXATION; ENTROPY; MOLECULAR RECOGNITION; THERMODYNAMICS;

BINDING INTERFACE; COMPLEX CONFIGURATION; ENTROPY PRODUCTION; HOMOGENEOUS CATALYSIS; HOST-GUEST COMPLEXATIONS; HOST-GUEST SYSTEM; ISOTHERMAL TITRATION CALORIMETRY; LIGAND DESIGN;

BINDING SITES;

EID: 20744454908     PISSN: 14394235     EISSN: None     Source Type: Journal    
DOI: 10.1002/cphc.200400559     Document Type: Article

References (39)

1. C. L. Hannon, E. V. Anslyn in Bioorganic Chemistry Frontiers, Vol. 3 (Eds.: F. P. Schmidtchen, H. Dugas), Springer, Berlin, 1993, pp. 193-255.
2. B. P. Orner, A. D. Hamilton, J. Inclusion Phenom. 2001, 41, 141-147.
3. M. D. Best, S. L. Tobey, E. V. Anslyn, Coord. Chem. Rev. 2003, 240, 3-15.
4. F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646.
5. a) F. P. Schmidtchen, Chem. Ber. 1980, 113, 2175-2182;
6. b) C. Schmuck, J. Org. Chem. 2000, 65, 2432-2437;
7. T. Haack, M. W. Peczuh, X. Salvatella, J. Sánchez-Quesada, J. de Mendoza, A. D. Hamilton, E. Giralt, J. Am. Chem. Soc. 1999, 121, 11813-11820;
8. A. Metzger, V. M. Lynch, E. V. Anslyn, Angew. Chem. 1997, 109, 911-914;
9. Angew. Chem. Int. Ed. Engl. 1997, 36, 862-865.
10. a) P. Schiessl, F. P. Schmidtchen, J. Org. Chem. 1994, 59, 509-511;
11. b) S. L. Tobey, E. V. Anslyn, J. Am. Chem. Soc. 2003, 125, 14807-14815;
12. S. L. Hauser, E. W. Johanson, H. P. Green, P. Smith, Org. Lett. 2000, 2, 3575-3578.
13. a) M. Berger, F. P. Schmidtchen, Angew. Chem. 1998, 110, 2840-2842;
14. Angew. Chem. Int. Ed. 1998, 37, 2694-2696;
15. b) M. Fibbioli, M. Berger, F. P. Schmidtchen, E. Pretsch, Anal. Chem. 2000, 72, 156-160.
16. F. P. Schmidtchen in Encyclopedia of Supramolecular Chemistry (Eds.: J. L. Atwood, J. Steed), Marcel Dekker, 2004, DOI: 10.1081/E-ESMC-120012656.
17. D. H. Waldeck, A. P. Sukharevsky, I. Read, B. Linton, A. D. Hamilton, J. Phys. Chem. B 1998, 102, 5394-5403.
18. X. Salvatella, M. Martinell, M. Gairi, M. G. Mateu, M. Feliz, A. D. Hamilton, J. de Mendoza, E. Giralt, Angew. Chem. 2004, 116, 198-200;
19. Angew. Chem. Int. Ed. 2004, 43, 196-198.
20. M. Garcia-Pérez, M. Pinto, J. A. Subirana, Biopolymers 2003, 69, 432-439.
21. M. H. V. Van Regenmortel, J. Mol. Recognit. 1999, 12, 1-2.
22. M. Berger, F. P. Schmidtchen, J. Am. Chem. Soc. 1999, 121, 9986-9993.
23. S. Otto, S. Kubik, J. Am. Chem. Soc. 2003, 125, 7804-7805.
24. M. Rekharsky, Y. Inoue, S. Tobey, A. Metzger, E. V. Anslyn, J. Am. Chem. Soc. 2002, 124, 14959-14967.
25. S. L. Wiskur, J. J. Lavigne, A. Metzger, S. L. Tobey, V. Lynch, E. V. Anslyn, Chem. Eur. J. 2004, 10, 3792-3804.
26. For a lucid discussion of the molecular interpretation of entropy, see: a) E. I. Kozliak, J. Chem. Educ. 2004, 87, 1595-1598;
27. b) R. M. Hanson, S. M. Green, Introduction to Molecular Thermodynamics, Integrated Graphics, Northfield, MN, 2000, and references therein.
28. F. P. Schmidtchen, Chem. Ber. 1980, 113, 2175-2182.
29. a) A. Gleich, F. P. Schmidtchen, Chem. Ber. 1990, 123, 907-915;
30. b) H. Kurzmeier, F. P. Schmidtchen, J. Org. Chem. 1990, 55, 3749-3755.
31. M. Haj-Zaroubi, N. Mitzel, F. P. Schmidtchen, Angew. Chem. 2002, 114, 111-114;
32. Angew. Chem. Int. Ed. 2002, 41, 104-107.
33. a) J. Cornforth, L. M. Huguenin, J. R. H. Wilson, J. Chem. Soc. Perkin Trans. 1 1987, 871 -875;
34. b) J. Cornforth, A. D. Robertson, J. Chem. Soc. Perkin Trans. 1 1987, 867-870.
35. The fidelity of the fit to the entire data set is much increased by including the higher-order complexes. However, as higher-order complexation affects only a small fraction in the titration run, the reliability of the numerical values reported is weak. The error minima probed are shallow, which leads to severe cross-correlations of these parameters.
36. F. Deanda, K. M. Smith, J. Liu, R. S. Pearlman, Mol. Pharm. 2004, 1, 23-39.
37. Structural definition may be viewed either by the sheer number of discrete molecular arrangements of host and guest including solvent, or through supplementation by molecular vibrations that are enabled on association involving all species. Both aspects refer to the entropy of binding.
38. F. P. Schmidtchen in Top. Curr. Chem., Vol. 255 (Ed.: I. Stibor), Springer, Heidelberg, 2005, 1-29.
39. L. D. Freedman, G. O. Doak, J. Org. Chem. 1956, 27, 238-239.