Encapsulation of ion-molecule complexes: Second-sphere supramolecular chemistry [26]

Journal of the American Chemical Society

Volumn 121, Issue 32, 1999, Pages 7455-7456

  Lützen, Arne ^a   Renslo, Adam R ^a   Schalley, Christoph A ^a   O'Leary, Brendan M ^a,b   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL STRUCTURE; ENCAPSULATION; LETTER; MASS SPECTROMETRY; MOLECULAR INTERACTION; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0344993966     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991747w     Document Type: Letter

References (23)

1. Dietrich, B. Cryptands. In Comprehensive Supramolecular Chemistry; Gokel, G. W., Ed.; Elsevier Science: New York, 1996; Vol. 1, Chapter 4.
2. Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, U.K., 1994.
3. Beno, B. R.; Sheu, C.; Houk, K. N.; Warmuth, R.; Cram, D. J. Chem. Commun. 1998, 301-302.
4. van Wageningen, A. M. A.; Andre, M. A.; Timmerman, P.; van Duynhoven, J. P. M.; Verboom, W.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Chem. Eur. J. 1997, 3, 639-654.
5. Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278-286.
6. Kang, J.; Santamaria, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389-7390.
7. Castellano, R. K.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3657-3663.
8. Szabo, T.; O'Leary, B. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1998, 37, 3410-3413.
9. Sherman, J. C.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2194-2204.
10. The new compound 3 was fully characterized by NMR and mass spectrometry.
11. MacroModel, Amber* force field: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
12. Volumes were calculated with the GRASP program: Nicholls, A.; Sharp, K. A.; Honig, B. Proteins: Struct., Funct., Genet. 1991, 11, 281-296.
13. A packing coefficient of 0.55% ± 0.09% appears to be ideal for guests with shapes congruent to that of the cavity. See: Mecozzi, S.; Rebek, J., Jr. Chem. Eur. J. 1998, 4, 1016-1022.
14. This unusual downfield shift has been observed earlier with smaller, but structurally similar, capsules and seems to be characteristic for guests inside this type of host. See ref 8.
15. 2O signals.
16. The simultaneous binding of anions and cations has been described a number of times and ion pairs less frequently. For a recent review, see: Antonisse, M. M. G.; Reinhoudt, D. N. Chem. Commun. 1998, 443-448.
17. Computational modeling found a packing coefficient of 0.85 for the proposed complex. This value exceeds that found in many super-dense solids.
18. For a description of our experimental methods and leading references on ESI-MS, see: Schalley, C. A.; Martin, T.; Obst, U.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 2133-2138.
19. 12) as evidenced by NMR spectroscopy.
20. For a discussion of the @ symbol in chemistry, see: Braun, T. ACH - Models Chem. 1996, 133, 427-428.
21. Incomplete desolvation seems unlikely because no signals have been observed that would indicate complexes of the capsule containing one or more solvent molecules in addition to the guest.
22. Vögtle, F.; Müller, W. M. Angew. Chem., Int. Ed. Engl. 1979, 18, 623-624.
23. Kamitori, S.; Hirotsu, K.; Higuchi, T. J. Am. Chem. Soc. 1987, 109, 9, 2409-2414.