Gating and entropy in guest exchange by Rebek's sportsballs. Theoretical studies of one-door, side-door, and back-door gating

Organic Letters

Volumn 1, Issue 4, 1999, Pages 591-594

  Wang, Xue ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000411878     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9900820     Document Type: Article

References (25)

1. Szabo, T.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 6193-6194.
2. Gracias, X.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1225-1228.
3. Rebek, J., Jr. Chem. Soc. Rev. 1996, 255-264.
4. Conn M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668.
5. Fox, T.; Thomas IV, B. E.; McCarrick, M.; Kollman, P. A. J. Phys. Chem. 1996, 100, 10779-10783.
6. Valdés, C.; Spitz, U. P.; Toledo, L. M.; Kubik, S. W.; Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 12733-12745.
7. Branda, N.; Grotzfeld, R. M.; Valdés, C.; Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 85-88.
8. Rivera, J. M.; Martin, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819-820.
9. Kang, J.; Santamaría, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389-7390.
10. Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239-241.
11. Meissner, R.; Gardas, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77-85.
12. Tokunaga, Y.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1997, 36, 2656-2659.
13. Rivera, J. M.; Martín, T.; Rebek, J., Jr. Science 1998, 279, 1021-1023.
14. Kang, J.; Hilmersson, G.; Santamaría, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650-3656.
15. Santamaría, J.; Martín, T.; Hilmersson, G.; Rebek, J., Jr., submitted for publication.
16. Rebek, J., Jr. Pure Appl. Chem. 1996, 68, 1261-1266.
17. Houk, K. N.; Nakamura, K.; Sheu, C. M.; Keating, A. E. Science 1996, 273, 627-629.
18. Nakamura, K.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 1853-1854.
19. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Canfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
20. Qiu, D.; Shenkin, P. S.; Hollinger, F. P.; Still, W. C. J. Phy. Chem. 1997, 101, 3005-3014.
21. Hammes, G. G.; Park, A. C. J. Am. Chem. Soc. 1968, 90, 4151-4157.
22. The dissociation energy is computed as ΔE = E(dimer) -2E(monomer).
23. Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1678-1683.
24. Computations using ab initio RHF/3-21G gave the same energy.
25. Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875-1917.