Synthesis and assembly of new molecular hosts: Solvation and the energetics of encapsulation

Journal of the American Chemical Society

Volumn 119, Issue 1, 1997, Pages 77-85

  Meissner, R ^b   Garcias, X ^b   Mecozzi, S ^b   Rebek Jr , J ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; COMPLEX FORMATION; COMPUTER SIMULATION; ENCAPSULATION; ENTHALPY; ENTROPY; HYDROGEN BOND; MOLECULAR DYNAMICS; TEMPERATURE;

EID: 0031049706     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962991f     Document Type: Article

References (43)

1. This phrase first appears as the title of a lecture by D. J. Cram at the C. David Gutsche Symposium, Washington University, St. Louis, Missouri, May 5, 1990; for examples, see: Cram, D. J. Nature 1992, 356, 29-36.
2. Cram, D. J.; Choi, H-J.; Bryant, J. A.; Knobler; C. B. J. Am. Chem. Soc. 1992, 114, 7748-7765. Cram, D. J.; Blanda, M. T.; Paek, K.; Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7765-7773.
3. Cram, D. J.; Choi, H-J.; Bryant, J. A.; Knobler; C. B. J. Am. Chem. Soc. 1992, 114, 7748-7765. Cram, D. J.; Blanda, M. T.; Paek, K.; Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7765-7773.
4. Collet, A. Tetrahedron 1987, 43, 5725. Canceill, J.; Cesario, M.; Collet, A.; Guilhem, J.; Lacombe, L.; Lozach, B.; Pascard, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 1246-1248.
5. Collet, A. Tetrahedron 1987, 43, 5725. Canceill, J.; Cesario, M.; Collet, A.; Guilhem, J.; Lacombe, L.; Lozach, B.; Pascard, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 1246-1248.
6. Chapman, R. G.; Chopra, N.; Cochien, E. D.; Sherman J. C. J. Am. Chem. Soc. 1994, 116, 369-370.
7. Sherman J. C.; Cram, D. J. J. Am. Chem. Soc. 1989, 111, 4527-4528.
8. Quan, M. L. C.; Knobler, C. B.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1991, 660-662. Quan, M. L. C.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2754-2755.
9. Quan, M. L. C.; Knobler, C. B.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1991, 660-662. Quan, M. L. C.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2754-2755.
10. Cram, D. J.; Tanner, M. E. Angew. Chem., Int. Ed. Engl. 1991, 30, 1024-1027.
11. Timmerman, P.; Verboom, W.; VanVeggel, F. C. J. M.; Duynhoven, J. P. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 2345-2348.
12. Wyler, R.; de Mendoza, J.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1993, 32, 1699-1701.
13. Shimizu, K. D.; Rebek, J., Jr. Proc. Natl. Acad. of Sci. U.S.A. 1995, 92, 12403-12407.
14. Meissner, R. S.; de Mendoza, J.; Rebek, J., Jr. Science 1995, 270, 1485-1488.
15. Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255.
16. Wintner, E.; Rebek, J., Jr. Acta Chem. Scand. 1996, 50, 469-485.
17. Rebek, J. Jr. Chem. Soc. Rev. In press.
18. Valdés, C.; Spitz, U. P.; Toledo, L.; Kubik, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 12733-12745.
19. Rebek, J., Jr. Acta Chem. Scand. 1996, 50, 707-716.
20. Toledo, L.; Valdes, C.; Rebek, J., Jr. Chem. Eur. J. 1996, 2, 989-991.
21. Branda, N.; Wyler, R.; Rebek, J., Jr. Science 1994, 263, 1267-1268. Branda, N.; Grotzfeld, R. M.; Valdés, C.; Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 85-88. For methane complexation inside a cryptophane see: Garel, L.; Dutasta, J.-P.; Collet, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1169.
22. Branda, N.; Wyler, R.; Rebek, J., Jr. Science 1994, 263, 1267-1268. Branda, N.; Grotzfeld, R. M.; Valdés, C.; Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 85-88. For methane complexation inside a cryptophane see: Garel, L.; Dutasta, J.-P.; Collet, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1169.
23. Branda, N.; Wyler, R.; Rebek, J., Jr. Science 1994, 263, 1267-1268. Branda, N.; Grotzfeld, R. M.; Valdés, C.; Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 85-88. For methane complexation inside a cryptophane see: Garel, L.; Dutasta, J.-P.; Collet, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1169.
24. Garcias, X.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1225-1228.
25. MacroModel V:5.5: Mohamadi, F.; Richards, N. G. J.; Guidia, W. C.; Liskamp, R.; Caulfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467. Although appropriate force field parameters for all the functional groups in molecule 1 do not exist, we believe that the use of the force field Amber* of MacroModel 5.5 allows a reasonable approximation for the calculation and comparison of volumes.
26. Beerli, R.; Rebek, J., Jr. Tetrahedron Lett. 1995, 36, 1813-1816.
27. C. Wilcox, personal communication. We thank Prof. Wilcox for providing this information prior to publication.
28. Saenger, W. Angew. Chem., Int. Ed. Engl. 1980, 19, 344-362 and references therein.
29. Cram, D. J.; Choi, H-J.; Bryant, J. A.; Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7748-7765. Cram, D. J.; Blanda, M. T.; Paek, K.; Knobler, C. B. J. Am. Chem. Soc 1992, 114, 7765-7773.
30. Cram, D. J.; Choi, H-J.; Bryant, J. A.; Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7748-7765. Cram, D. J.; Blanda, M. T.; Paek, K.; Knobler, C. B. J. Am. Chem. Soc 1992, 114, 7765-7773.
31. For a recent discussion with leading references, see: Dunitz, J. D. Chem. Biol. 1995, 2, 709-712.
32. Peterson, B. R.; Wallimann, P.; Carcanague, D. R.; Diederich, F. Tetrahedron 1995, 51, 401-421.
33. Searle, M. S.; Westwell, M. S.; Williams, D. H. J. Chem. Soc., Perkin Trans. 2 1995, 141-151.
34. Canceill, J.; Cesario, M.; Collet, A.; Guilhem, J.; Lacombe, L.; Lozach, B.; Pascard, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 1246-1248.
35. Craven, I. E.; Hesling, M. R.; Laver, D. R.; Lukins, P. B.; Ritchie, G. L. D.; Vrbancich, J. J. Phys. Chem. 1989, 93, 627.
36. Gentle, I. R.; Ritchie, G. L. D. J. Phys. Chem. 1989, 93, 7740.
37. Helgeson, R. C.; Paek, K.; Knobler, C. B.; Maverick, E. B.; Cram, D. J. J. Am. Chem. Soc. 1996, 118, 5590-5604.
38. Chapman, R. G.; Sherman J. C. J. Am. Chem. Soc. 1995, 117, 9081-9082.
39. Temperature was kept constant at 300 K during the whole simulation. Total time = 100 ps, time steps = 1 fs. GB/SA chloroform solvation was used.
40. Nicholls, A.; Sharp, K. A., Honig, B. Proteins 1991, 11, 281.
41. This task is automatically accomplished by GRASP. During the triangulation of the surfaces of the two softball halves for the calculation of the interior volume, the program calculates the average position of all the triangles at the edges of these surfaces. Joining of these edges generates the surface of the internal cavity.
42. The occupancy factor of a guest molecule in the cavity of a host is usually defined as the ratio of the van der Waals radius of the guest to the volume of the cavity calculated on the van der Waals interior surface of the host. We calculated this factor based on the volumes generated by the program GRASP.
43. T = 300 K, total time = 150 ps, time step = 1fs. GB/SA chloroform solvation was used.