Structural rules governing self-assembly emerge from new molecular capsules

Journal of the American Chemical Society

Volumn 120, Issue 4, 1998, Pages 819-820

  Rivera, José M ^a,b   Martín, Tomás ^b   Rebek Jr , Julius ^b  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ENCAPSULATION; HYDROGEN BOND; MICROCAPSULE; NONHUMAN;

EID: 0032481321     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973341u     Document Type: Article

References (15)

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2. (b) Kang, J.; Rebek, Jr., J. Nature 1996, 382, 239.
3. (c) Conn, M. M.; Rebek, Jr., J. Chem. Rev. 1997, 97, 1647.
4. Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1997, 36, 846.
5. The compounds 2 and 3 were obtained together with their corresponding geometrical isomers (2s, 2w, 3s, 3w), which were separated by chromatographic methods. Tokunaga, Y.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1997, 36, 2656-2659.
6. Results obtained from the GRASP program. Nicholls, A.; Sharp, K. A.; Honig, B. Proteins 1991, 11, 281.
7. (aggregate)][g] (1)
8. The assumptions are (1) the amount of dimer (unfilled or filled with solvent) present before addition of the guest is negligible, (2) after addition of the guest, all of the host material not assembled into the capsule is in the aggregate state, and (3) the association of the guest with itself is negligible.
9. a
10. a for 21 was then used to calculate constants for the rest of the guests 15-20 by competition experiments.
11. Garel, L.; Dutasta, J.; Collet, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1169.
12. (a) Koh, K.; Araki, K.; Shinkai, S. Tetrahedron Lett. 1994, 35, 8255.
13. (b) Valdés, C.; Spitz, U. P.; Toledo, L. M.; Kubik, S. W.; Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 12733.
14. (c) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489.
15. Molecular modeling was performed using MACROMODEL 5.5 (MM2* force field). These distances were obtained from the energy-minimized structures of the corresponding dimers. Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.