Heterocycles in encapsulation and assembly

Heterocycles

Volumn 52, Issue 1, 2000, Pages 493-504

  Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Encapsulation; Hydrogen bonding; Molecular recognition; Self assembly

Indexed keywords

HETEROCYCLIC COMPOUND; SOLVENT;

CATALYST; ENCAPSULATION; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; REVIEW; STEREOISOMERISM; SYNTHESIS;

EID: 0033978651     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-99-SR1     Document Type: Review

References (34)

1. For relevant behavior of covalently-bound molecule-within molecule capsules see R.C. Helgeson, K. Paek, C.B. Knobler, E.B. Maverick, and D.J. Cram, J. Am. Chem. Soc., 1996, 118, 5590.
2. A. Collet, J.P. Dutasta, B. Lozach, and J. Canceill, 'Topics in Current Chemistry, 165: Chemistry I-Directed Synthesis and Molecular Recognition,' ed. by E. Weber, Springer Verlag, Berlin, 1993, pp. 104.
3. For related processes that occur in covalently bound hosts see: D.J. Cram, M.E. Tanner, and R. Thomas, Angew. Chem., Int. Int. Ed. Engl., 1991, 30, 1024; R. Warmuth, Chem. Commun., 1998, 59.
4. For related processes that occur in covalently bound hosts see: D.J. Cram, M.E. Tanner, and R. Thomas, Angew. Chem., Int. Int. Ed. Engl., 1991, 30, 1024; R. Warmuth, Chem. Commun., 1998, 59.
5. P. Timmerman, W. Verboom, F.C.J.M. van Veggel, W.P. van Hoorn, and D.N. Reinhoudt, Angew. Chem., Int. Ed. Engl., 1994 33, 1292.
6. L.M. Tunstad, J.A. Tucker, E. Dalcanale, J. Weiser, J.A. Bryant, J.C. Sherman, R.C. Helgeson, C.B. Knobler, and D.J. Cram, J. Org. Chem., 1989, 54, 1305; D.J. Cram, H-J. Choi, J.A. Bryant, and C.B. Knobler, J. Am. Chem. Soc., 1992, 114, 7748; J.R. Moran, J.L. Ericson, E. Dalcanale, J.A. Bryant, C.B. Knobler, and D.J. Cram, J. Am. Chem. Soc., 1991, 113, 5707.
7. L.M. Tunstad, J.A. Tucker, E. Dalcanale, J. Weiser, J.A. Bryant, J.C. Sherman, R.C. Helgeson, C.B. Knobler, and D.J. Cram, J. Org. Chem., 1989, 54, 1305; D.J. Cram, H-J. Choi, J.A. Bryant, and C.B. Knobler, J. Am. Chem. Soc., 1992, 114, 7748; J.R. Moran, J.L. Ericson, E. Dalcanale, J.A. Bryant, C.B. Knobler, and D.J. Cram, J. Am. Chem. Soc., 1991, 113, 5707.
8. L.M. Tunstad, J.A. Tucker, E. Dalcanale, J. Weiser, J.A. Bryant, J.C. Sherman, R.C. Helgeson, C.B. Knobler, and D.J. Cram, J. Org. Chem., 1989, 54, 1305; D.J. Cram, H-J. Choi, J.A. Bryant, and C.B. Knobler, J. Am. Chem. Soc., 1992, 114, 7748; J.R. Moran, J.L. Ericson, E. Dalcanale, J.A. Bryant, C.B. Knobler, and D.J. Cram, J. Am. Chem. Soc., 1991, 113, 5707.
9. T. Heinz and D.M. Rudkevich, Nature, 1998, 394, 764.
10. F. Mohamadi, N. G. Richards, W. C. Guida, R. Liskamp, C. Caufield, G. Chang, T. Hendrickson, and W. C. Still, J. Comput. Chem., 1990, 11, 440; D. Q. McDonald and W. C. Still, Tetrahedron Lett., 1992, 33, 7743.
11. F. Mohamadi, N. G. Richards, W. C. Guida, R. Liskamp, C. Caufield, G. Chang, T. Hendrickson, and W. C. Still, J. Comput. Chem., 1990, 11, 440; D. Q. McDonald and W. C. Still, Tetrahedron Lett., 1992, 33, 7743.
12. R.G. Chapman and J.C. Sherman, J. Am. Chem. Soc., 1995, 117, 9081.
13. J. Kang and J. Rebek, Jr., Nature, 1996, 382, 239.
14. J. Kang and J. Rebek, Jr., Nature, 1997, 385, 50.
15. J. Kang, G. Hilmersson, J. Santamaría, and J. Rebek, Jr., J. Am. Chem. Soc., 1998, 120, 3650.
16. D. Hilvert, K.W. Hill, and M.T.M. Auditor, J. Am. Chem. Soc., 1989, 111, 9261.
17. For cycloaddition inside a cucurbituril see: W.L. Mock, T.A. Irra, J.P. Wepsiec, and M. Adhya, J. Org. Chem., 1989, 54, 5302.
18. T. Martin, U. Obst, and J. Rebek, Jr., Science, 1998, 281, 1842.
19. K. C. Russell, E. Leize, A. Van Dorsselaer, and J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 1995, 34, 209.
20. K.A. Jolliffe, M.C. Calama, R. Fokkens, N.M.M. Nibbering, P. Timmerman, and D.N. Reinhoudt, Angew. Chem., Int. Ed. Engl., 1998, 37, 1247.
21. X. Cheng, Q. Gao, R.D. Smith, E.E. Simanek, M. Mammen, and G.M. Whitesides, J. Org. Chem., 1996, 61, 2204.
22. For reviews of MS applications in supramolecular chemistry see: M. Vicenti, E. Pelizzetti, E. Dalcanale, and P. Soncini, Pure Appl. Chem., 1993, 65, 1507; M. Vicenti, C. Minero, E. Pelizzetti, A. Secchi, and E. Dalcanale, Pure Appl. Chem., 1995, 67, 1075; M. Vicenti, J. Mass Spectrom., 1995, 30, 925; M. Przybylski and M.O. Glocker, Angew. Chem., Int. Ed. Engl., 1996, 35, 806.
23. For reviews of MS applications in supramolecular chemistry see: M. Vicenti, E. Pelizzetti, E. Dalcanale, and P. Soncini, Pure Appl. Chem., 1993, 65, 1507; M. Vicenti, C. Minero, E. Pelizzetti, A. Secchi, and E. Dalcanale, Pure Appl. Chem., 1995, 67, 1075; M. Vicenti, J. Mass Spectrom., 1995, 30, 925; M. Przybylski and M.O. Glocker, Angew. Chem., Int. Ed. Engl., 1996, 35, 806.
24. For reviews of MS applications in supramolecular chemistry see: M. Vicenti, E. Pelizzetti, E. Dalcanale, and P. Soncini, Pure Appl. Chem., 1993, 65, 1507; M. Vicenti, C. Minero, E. Pelizzetti, A. Secchi, and E. Dalcanale, Pure Appl. Chem., 1995, 67, 1075; M. Vicenti, J. Mass Spectrom., 1995, 30, 925; M. Przybylski and M.O. Glocker, Angew. Chem., Int. Ed. Engl., 1996, 35, 806.
25. For reviews of MS applications in supramolecular chemistry see: M. Vicenti, E. Pelizzetti, E. Dalcanale, and P. Soncini, Pure Appl. Chem., 1993, 65, 1507; M. Vicenti, C. Minero, E. Pelizzetti, A. Secchi, and E. Dalcanale, Pure Appl. Chem., 1995, 67, 1075; M. Vicenti, J. Mass Spectrom., 1995, 30, 925; M. Przybylski and M.O. Glocker, Angew. Chem., Int. Ed. Engl., 1996, 35, 806.
26. Electrospray Ionization Mass Spectrometry, R.B. Cole, Ed., Wiley, New York, 1997.
27. C.A. Schalley, T. Martin, U. Obst, and J. Rebek, Jr., "Characterization of Encapsulation complexes in the Gas Phase and Solution", J. Am. Chem. Soc., 1999, in press.
28. O. Mogck, V. Böhmer, and W. Vogt, Tetrahedron, 1996, 52, 8489; J.M. Rivera, T. Martin, and J. Rebek, Jr., J. Am. Chem. Soc., 1998, 120, 819.
29. O. Mogck, V. Böhmer, and W. Vogt, Tetrahedron, 1996, 52, 8489; J.M. Rivera, T. Martin, and J. Rebek, Jr., J. Am. Chem. Soc., 1998, 120, 819.
30. R.K. Castellano, D.M. Rudkevich, and J. Rebek, Jr., J. Am. Chem. Soc., 1996, 118, 10002.
31. J.C. Ma and D.A. Dougherty, Chem. Rev., 1997, 97, 1303; J.B. Fenn, M. Mann, C.K. Meng, S.F. Wong, and C.M. Whitehouse, Mass Spectrom. Rev., 1990, 9, 37; P. Kebarle and L. Tang, Anal. Chem., 1993, 65, 972A; S.J. Gaskell, J. Mass Spectrom., 1997, 32, 677.
32. J.C. Ma and D.A. Dougherty, Chem. Rev., 1997, 97, 1303; J.B. Fenn, M. Mann, C.K. Meng, S.F. Wong, and C.M. Whitehouse, Mass Spectrom. Rev., 1990, 9, 37; P. Kebarle and L. Tang, Anal. Chem., 1993, 65, 972A; S.J. Gaskell, J. Mass Spectrom., 1997, 32, 677.
33. J.C. Ma and D.A. Dougherty, Chem. Rev., 1997, 97, 1303; J.B. Fenn, M. Mann, C.K. Meng, S.F. Wong, and C.M. Whitehouse, Mass Spectrom. Rev., 1990, 9, 37; P. Kebarle and L. Tang, Anal. Chem., 1993, 65, 972A; S.J. Gaskell, J. Mass Spectrom., 1997, 32, 677.
34. J.C. Ma and D.A. Dougherty, Chem. Rev., 1997, 97, 1303; J.B. Fenn, M. Mann, C.K. Meng, S.F. Wong, and C.M. Whitehouse, Mass Spectrom. Rev., 1990, 9, 37; P. Kebarle and L. Tang, Anal. Chem., 1993, 65, 972A; S.J. Gaskell, J. Mass Spectrom., 1997, 32, 677.