Kinetically Stable Complexes in Water: The Role of Hydration and Hydrophobicity

Journal of the American Chemical Society

Volumn 126, Issue 9, 2004, Pages 2870-2876

  Biros, Shannon M ^a   Ullrich, Elke C ^a   Hof, Fraser ^a   Trembleau, Laurent ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALORIMETRY; COMPLEXATION; MICELLES; PH EFFECTS; REACTION KINETICS; SYNTHESIS (CHEMICAL); THERMODYNAMICS; TITRATION; WATER;

ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR RECEPTORS;

AROMATIC COMPOUNDS;

BUFFER; CARBOXYLIC ACID; DODECYL SULFATE SODIUM; SODIUM CHLORIDE; WATER;

ARTICLE; CALORIMETRY; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONCENTRATION RESPONSE; HYDRATION; HYDROPHOBICITY; KINETICS; MEASUREMENT; MICELLE; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; SYNTHESIS; THERMODYNAMICS; TITRIMETRY;

BENZIMIDAZOLES; ETHERS, CYCLIC; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; QUATERNARY AMMONIUM COMPOUNDS; RESORCINOLS; THERMODYNAMICS; WATER;

EID: 1542347929     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038823m     Document Type: Article

References (47)

1. Webb, T. H.; Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 8554-8555.
2. Méric, R.; Vigneron, J.-P.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1993, 129-131.
3. Ngola, S. M.; Dougherty, D. A. J. Org. Chem. 1998, 63, 4566-4567.
4. Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192-1201.
5. Kano, K.; Kitae, T.; Shimofuri, Y.; Tanaka, N.; Mineta, Y. Chem.-Eur. J. 2000, 6, 2705-2713.
6. Metzger, A.; Lynch, V. M.; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 862.
7. Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649-652.
8. Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763.
9. Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533-8534.
10. Rekharsky, M.; Inoue, Y.; Tobey, S.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 2002, 124, 14959-14967.
11. Atwood, J. L.; Barbour, L. J.; Junk, P. C.; Orr, G. W. Supramol. Chem. 1995, 5, 105-108.
12. Lehn, J.-M.; Meric, R.; Vigneron, J.-P.; Cesario, M.; Guilhem, J.; Pascard, C.; Asfari, Z.; Vicens, J. Supramol. Chem. 1995, 5, 97-103.
13. Sansone, F.; Barboso, S.; Casnati, A.; Sciotto, D.; Ungaro, R. Tetrahedron Lett. 1999, 40, 4741-4744.
14. Arena, G.; Contino, A.; Fujimoto, T.; Sciotto, D.; Aoyama, Y. Supramol. Chem. 2000, 11, 279-288.
15. Park, S. J.; Hong, J.-I. Tetrahedron Lett. 2000, 41, 8311-8315.
16. Lazzarotto, M.; Sansone, F.; Baldini, L.; Casnati, A.; Cozzini, P.; Ungaro, R. Eur. J. Org. Chem. 2001, 595-602.
17. Corbellini, F.; Costanzo, L. D.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947.
18. Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907-908.
19. Jain, R. K.; Hamilton, A. D. Org. Lett. 2000, 2, 1721-1723.
20. Mizutani, T.; Wada, K.; Kitagawa, S. J. Am. Chem. Soc. 2001, 123, 6459-6460.
21. Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975.
22. See, for example, Zadmard, R.; Junkers, M.; Schrader, T.; Grawe, T.; Kraft, A. J. Org. Chem. 2003, 68, 6511-6521.
23. Hof, F.; Trembleau, L.; Ullrich, E. C.; Rebek, J. J. Angew. Chem., Int. Ed. 2003, 42, 3150-3153.
24. Amrhein, P.; Shivanyuk, A.; Johnson, D. W.; Rebek, J. J. J. Am. Chem. Soc. 2002, 124, 10349.
25. Church, T. J.; Cutshall, N. S.; Gangloff, A. R.; Jenkins, T. E.; Linsell, M. S.; Litvak, J.; Rice, K. D.; Spencer, J. R.; Wang, V. R. (Axys Pharmaceuticals Corp.). PCT Int. Appl. WO 97-US21849, 1998; p 108.
26. Cram, D. J.; Choi, H.-J.; Bryant, J. A.; Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7748-7765.
27. Haino, T.; Rudkevich, D. M.; Rebek, J. J. J. Am. Chem. Soc. 1999, 121, 11253-11254.
28. Haino, T.; Rudkevich, D. M.; Shivanyuk, A.; Rissanen, K.; Rebek, J. J. Chem.-Eur. J. 2000, 6, 3797-3805.
29. Far, A. R.; Shivanyuk, A.; Rebek, J. J. J. Am. Chem. Soc. 2002, 124, 2854-2855.
30. Diederich, F. Cyclophanes: Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, U.K., 1991.
31. Two guests, choline chloride (11) and tetraethylammonium bromide (10), generated negative entropic values, with choline's being strongly negative at -10.0 cal/(mol K). As this guest also gave an "n" value of 0.6, it is possible there may be another association process occurring in solution which is not detectable by NMR. Please see the Supporting Information for raw ITC data and other thermodynamic values.
32. Johnson, Darren W. Personal communication. For nicotine binding, please see: Terpin, A. J.; Ziegler, M.; Johnson, D. W.; Raymond, K. N. Angew. Chem., Int. Ed. 2001, 40, 157-160.
33. Johnson, Darren W. Personal communication. For nicotine binding, please see: Terpin, A. J.; Ziegler, M.; Johnson, D. W.; Raymond, K. N. Angew. Chem., Int. Ed. 2001, 40, 157-160.
34. Hansch, C.; Leo, A. Exploring QSAR: Fundamentals and Applications in Chemistry and Biology; American Chemical Society: Washington, DC, 1995.
35. Leto, J. R.; Leto, M. F. J. Am. Chem. Soc. 1961, 83, 2944-2951.
36. Imai, H.; Yaehashi, Y.; Misuno, Y. Nippon Kagaku Zasshi 1969, 90, 1048-1050.
37. Glasoe, P. K.; Long, F. A. J. Phys. Chem. 1960, 64, 188.
38. Zadmard, R.; Junkers, M.; Schrader, T.; Grawe, T.; Kraft, A. J. Org. Chem. 2003, 68, 6511-6521.
39. It is surprising that the host binds only amantadine in the presence of both adamantane derivatives when the association constant for rimantadine is at least an order of magnitude greater, and that this binding does not saturate the host.
40. Hofmeister, F. Arch. Exp. Pathol. Pharmakol. 1888, 24, 247.
41. Cacace, M. G.; Landau, E. M.; Ramsden, J. J. Q. Rev. Biophys. 1997, 30, 241-277.
42. Trembleau, L.; Rebek, J. J. Chem. Commun. 2004, 58-59.
43. Kornhuber, J.; Schoppmeyer, K.; Riederer, P. Neurosci. Lett. 1993, 163, 129-131.
44. McGahen, J. W.; Neumayer, E. M.; Grunert, R. R.; Hoffmann, C. E. Ann. N. Y. Acad. Sci. 1970, 173 (Art. 1), 557-567.
45. Sklenar, V.; Piotto, M.; Leppik, R.; Saudek, V. J. Magn. Reson., Ser. A 1993, 102, 241-245.
46. Piotto, M.; Saudek, V.; Sklenar, V. J. Biomol. NMR 1992, 2, 661-666.
47. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.