Acceleration of amide bond rotation by encapsulation in the hydrophobic interior of a water-soluble supramolecular assembly

Journal of Organic Chemistry

Volumn 73, Issue 18, 2008, Pages 7132-7136

  Pluth, Michael D ^a   Bergman, Robert G ^a   Raymond, Kenneth N ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CHEMICAL REACTIONS; ENCAPSULATION; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY;

AMIDE BONDS; CHEMICAL EQUATIONS; HYDROPHOBIC EFFECTS; SELF-ASSEMBLED; SUPRAMOLECULAR ASSEMBLIES; TERTIARY AMIDES; VARIABLE TEMPERATURES;

HYDROPHOBICITY;

AMIDE; CARBON 13; CARBONYL DERIVATIVE;

ACCELERATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; ENCAPSULATION; ENERGY; HYDROPHOBICITY; ISOTOPE LABELING; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILITY; TEMPERATURE DEPENDENCE;

AMIDES; CARBON ISOTOPES; HYDROPHOBICITY; ISOTOPE LABELING; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ROTATION; SOLUBILITY; TEMPERATURE; THERMODYNAMICS; WATER;

EID: 52449093620     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800991g     Document Type: Article

References (38)

1. Fischer, G. Angew. Chem., Int. Ed. 1994, 33, 1415.
2. Lummis, S. C. R.; Beene, D. L.; Lee, L. W.; Lester, H. A.; Broadhurst, R. W.; Dougherty, D. A. Nature 2005, 438, 248.
3. Wiberg, K. B.; Breneman, C. L. J. Am. Chem. Soc. 1992, 114, 831.
4. Wiberg, K. B.; Laidig, K. E. J. Am. Chem. Soc. 1987, 109, 5935.
5. Perrin, C. L. J. Am. Chem. Soc. 1991, 113, 2865.
6. Gatti, C.; Fantucci, P. J. Phys. Chem. 1993, 97, 11677.
7. Laidig, K. E. J. Am. Chem. Soc. 1992, 114, 7912.
8. Lauvergnat, D.; Hiberty, P. C. J. Am. Chem. Soc. 1997, 119, 9478.
9. Fischer, G. Chem. Soc. Rev. 2000, 29, 119.
10. Mohanty, J.; Bhasikuttan, A. C.; Nau, W. M.; Pal, H. J. Phys. Chem. B 2006, 110, 5132.
11. Kallen, J.; Spitzfaden, C.; Zurini, M. G. M.; Wider, G.; Widmer, H.; Wuthrich, K.; Walkinshaw, M. D. Nature 1991, 353, 276.
12. Michnick, S. W.; Rosen, M. K.; Wandless, T. J.; Karplus, M.; Schreiber, S. L. Science 1991, 252, 836.
13. Moore, J. M.; Peattie, D. A.; Fitzgibbon, M. J.; Thompson, J. A. Nature 1991, 351, 248.
14. Van Duyne, G. D.; Standaert, R. F.; Karplus, P. A.; Schreiber, S. L.; Clardy, J. Science 1991, 252, 839.
15. Kofron, J. L.; Kuzmic, P.; Kishore, V.; Colon-Bonilla, E.; Rich, D. H. Biochemistry 1991, 30, 6127.
16. Salvio, R.; Moisan, L.; Ajami, D.; Rebek, J., Jr Eur. J. Org. Chem. 2007, 16, 2722.
17. Sherman, J. C.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2194.
18. Caulder, D. L.; Powers, R. E.; Parac, T. N.; Raymond, K. N. Angew. Chem., Int. Ed. 1998, 37, 1840.
19. Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975.
20. Davis, A. V.; Fiedler, D.; Seeber, G.; Zahl, A.; van Eldik, R.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 1324.
21. Davis, A. V.; Raymond, K. N. J. Am. Chem. Soc. 2005, 127, 7912.
22. Fiedler, D.; Leung, D. H.; Bergman, R. G.; Raymond, K. N. Acc. Chem. Res. 2005, 38, 349.
23. Brumaghim, J. L.; Michels, M.; Pagliero, D.; Raymond, K. N. Eur. J. Org. Chem. 2004, 24, 5115.
24. Dong, V. M.; Fiedler, D.; Carl, B.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 14464.
25. Ziegler, M.; Brumaghim, J. L.; Raymond, K. N. Angew. Chem., Int. Ed. 2000, 39, 4119.
26. Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2004, 43, 6748-6751.
27. Davis, A. V.; Fiedler, D.; Seeber, G.; Zahl, A.; van Eldik, R.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 1324.
28. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Science 2007, 316, 85.
29. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 11459.
30. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2007, 119, 8741.
31. Biros, S. M.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 12094.
32. Allerhand, A.; Gutowsky, H. S.; Jonas, J.; Meinzer, R. A. J. Am. Chem. Soc. 1966, 88, 3185.
33. Drakenberg, T.; Dahlqvist, K. I.; Forsen, S. J. Phys. Chem. 1972, 76, 2178.
34. Eberhardt, E. S.; Loh, S. N.; Hinck, A. P.; Raines, R. T. J. Am. Chem. Soc. 1992, 114, 5437.
35. Yamada, S. Angew. Chem., Int. Ed. 1995, 24, 1113.
36. Yamada, S. J. Org. Chem. 1996, 61, 941.
37. Frisch, M. J. et al. Gaussian 03, Revision D.01, Gaussian, Inc.: Wallingford, CT, 2004.
38. Amman, C.; Meier, P.; Merbach, A. E. J. Magn. Reson. A 1982, 46, 319.