Does size really matter? The steric isotope effect in a supramolecular host-guest exchange reaction

Angewandte Chemie - International Edition

Volumn 49, Issue 21, 2010, Pages 3635-3637

  Mugridge, Jeffrey S ^a   Bergman, Robert G ^a   Raymond, Kenneth N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Host guest systems; Isotope effects; Kinetics; Noncovalent interactions; Supramolecular chemistry

Indexed keywords

HOST-GUEST SYSTEM; ISOTOPE EFFECT; ISOTOPE EFFECTS; NON-COVALENT INTERACTION; NONCOVALENT INTERACTIONS;

CARRIER MOBILITY; DEUTERIUM; MACROMOLECULES;

SUPRAMOLECULAR CHEMISTRY;

EID: 77952388251     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906569     Document Type: Article

References (28)

1. A. Konen, H. Limbach, Isotope Effects in Chemistry and Biology, Taylor & Francis, London, 2006.
2. D. Wade, Chem.-Biol. Interact. 1999, 117, 191-217.
3. K. Kuchitsu, L. S. Barteil, J. Chem. Phys. 1962, 36, 2470-2481.
4. N. L. Allinger, H. L. Flanagan, J. Comput. Chem. 1983, 4, 399-403.
5. J. D. Dunitz, R. M. Ibberson, Angew. Chem. 2008, 120, 4276-4278;
6. Angew. Chem. Int. Ed. 2008, 47, 4208-4210.
7. L. Melander, R. E. Carter, J. Am. Chem. Soc. 1964, 86, 295-296.
8. K. Mislow, R. Graeve, A. J. Gordon, G. H. Wahl, Jr., J. Am. Chem. Soc. 1964, 86, 1733-1741.
9. S. A. Sherrod, R. L. Costa, R. A. Barnes, V. Boekelheide, J. Am. Chem. Soc 1974, 96, 1565-1577.
10. T. Felder, C. A. Schalley, Angew. Chem. 2003, 115, 2360-2363;
11. Angew. Chem. Int. Ed 2003, 42, 2258-2260.
12. These types of KIEs have classically been explained in terms of a difference between C-H/D bond distances (a consequence of the anharmonicity of the potential function and the different ZPEs of the C-H/D bonds) and this is the context in which we frame our introduction. As we subsequently describe, these IEs are more fully explained by changes in the shape of potential energy wells at the transition state and the differences in coupling of vibrational modes with the host deformation.
13. D. L. Caulder, R. E. Powers, T. N. Parac, K. N. Raymond, Angew. Chem. 1998, 110, 1940-1943
14. ; Angew. Chem. Int. Ed. 1998, 37, 1840-1843.
15. M. D. Pluth, D. W. Johnson, G. Szigethy, A. V. Davis, S. J. Teat, A. G. Oliver, R. G. Bergman, K. N. Raymond, Inorg. Chem. 2009, 48, 111-120.
16. T. N. Parac, D. L. Caulder, K. N. Raymond, J. Am. Chem. Soc. 1998, 120, 8003-8004.
17. D. Fiedler, D. Pagliero, J. L. Brumaghim, R. G. Bergman, K. N. Raymond, Inorg. Chem. 2004, 43, 846-848.
18. S. M. Biros, R. G. Bergman, K. N. Raymond, J. Am. Chem. Soc. 2007, 129, 12094-12095.
19. C. Hastings, M. D. Pluth, S. M. Biros, R. G. Bergman, K. N. Raymond, Tetrahedron 2008, 64, 8362-8367.
20. D. Fiedler, D. H. Leung, R. G. Bergman, K. N. Raymond, Acc. Chem. Res. 2005, 38, 349-358.
21. M. D. Pluth, R. G. Bergman, K. N. Raymond, Acc. Chem. Res 2009, 42, 1650-1659.
22. A. V. Davis, K. N. Raymond, J. Am. Chem. Soc 2005, 127, 79127919.
23. A. V. Davis, D. Fiedler, G. Seeber, A. Zahl, R. van Eldik, K. N. Raymond, J. Am. Chem. Soc. 2006, 128, 1324-1333.
24. D. H. Leung, R. G. Bergman, K. N. Raymond, J. Am. Chem. Soc. 2006, 128, 9781-9797.
25. Y Zhao, K. N. Houk, D. Rechavi, A. Scarso, J. Rebek, Jr., J Am. Chem. Soc 2004, 126, 11428-11429.
26. T. Hayama, K. K. Baldridge, Y.-T. Wu, A. Linden, J. S. Siegel, J. Am. Chem. Soc 2008, 130, 1583-1591.
27. T. Haino, K. Fukuta, I. Hajime, S. Iwata, Chem. Eur. J. 2009, 15, 13286-13290.
28. C. Chang, M. K. Gilson, J. Am. Chem. Soc. 2004, 126, 13156-13164.