Guest packing motifs within a supramolecular nanocapsule and a covalent analogue

Journal of the American Chemical Society

Volumn 135, Issue 11, 2013, Pages 4314-4324

  Liu, Simin ^a   Russell, David H ^b   Zinnel, Nathanael F ^b   Gibb, Bruce C ^a  

^a Tulane University   (United States)

^b TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GUEST MOLECULES; HYDROPHOBIC EFFECT; N-ALKANES; NMR DIFFUSION; PACKING MOTIFS; RELATIVE STABILITIES; SMOOTH TRANSITIONS;

SYNTHESIS (CHEMICAL);

CHEMISTRY;

METHYL GROUP; NANOCAPSULE;

ANISOTROPY; AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; CONFORMATION; CONTROLLED STUDY; DIFFUSION TENSOR IMAGING; ENCAPSULATION; HYDROPHOBICITY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SUPRAMOLECULAR CHEMISTRY;

ACIDS; ALKANES; DIAMINES; DIMERIZATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MODELS, MOLECULAR; NANOCAPSULES;

EID: 84875445995     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja310741q     Document Type: Article

References (44)

1. Tanaka, H.; Kato, K.; Yamashita, E.; Sumizawa, T.; Zhou, Y.; Yao, M.; Iwasaki, K.; Yoshimura, M.; Tsukihara, T. Science 2009, 323, 384-388
2. Xu, Z.; Horwich, A. L.; Sigler, P. B. Nature 1997, 388, 741-750
3. Horwich, A. L.; Farr, G. W.; Fenton, W. A. Chem. Rev. 2006, 106, 1917-1930
4. Clantin, B.; Delattre, A. S.; Rucktooa, P.; Saint, N.; Meli, A. C.; Locht, C.; Dubuisson, F. J.; Villeret, V. Science 2007, 317, 957-961
5. Sacchettini, J. C.; Gordon, J. I.; Banaszak, L. J. J. Mol. Biol. 1989, 208 (2) 327-39
6. Brown, C. J.; Miller, G. M.; Johnson, M. W.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2011, 133 (31) 11964-6
7. Murase, T.; Horiuchi, S.; Fujita, M. J. Am. Chem. Soc. 2010, 132, 2866-2867
8. Crisostomo, F. R. P.; Lkedo, A.; Shenoy, S. R.; Iwasawa, T.; Rebek, J., Jr. J. Am. Chem. Soc. 2009, 131, 7402-7410
9. Shenoy, S. R.; Crisostomo, F. R. P.; Iwasawa, T.; Rebek, J., Jr. J. Am. Chem. Soc. 2008, 130, 5658-5659
10. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2008, 130, 11423-11429
11. Yamaguchi, T.; Fujita, M. Angew. Chem., Int. Ed. 2008, 47, 2067-2069
12. Nishioka, Y.; Yamaguchi, T.; Kawano, M.; Fujita, M. J. Am. Chem. Soc. 2008, 130, 8160-8161
13. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Science 2007, 316, 85-88
14. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2007, 46, 8587-8589
15. Nishioka, Y.; Yamaguchi, T.; Yoshizawa, M.; Fujita, M. J. Am. Chem. Soc. 2007, 129, 7000-7001
16. Fiedler, D.; van Halbeek, H.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 10240-10252
17. Yoshizawa, M.; Tamura, M.; Fujita, M. Science 2006, 312, 251-254
18. Hooley, R. J.; Rebek, J., Jr. J. Am. Chem. Soc. 2005, 127, 11904-11905
19. Chen, J.; Rebek, J., Jr. Org. Lett. 2002, 4, 327-329
20. Kang, J.; Santamaría, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389-7390
21. Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50-52
22. Gibb, C. L. D.; Gibb, B. C. J. Am. Chem. Soc. 2006, 128, 16498-16499
23. Liu, S.; Gan, H.; Hermann, A. T.; Rick, S. W.; Gibb, B. C. Nat. Chem. 2010, 2, 847-852
24. Trembleau, L.; Rebek, J., Jr. Science 2003, 301, 1219-1220
25. Scarso, A.; Trembleau, L.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2003, 42, 5499-5502
26. Scarso, A.; Trembleau, L.; Rebek, J., Jr. J. Am. Chem. Soc. 2004, 126, 13512-13518
27. Gibb, C. L. D.; Gibb, B. C. Chem. Commun. 2007, 1635-1637
28. Rebek, J., Jr. Chem. Commun. 2007, 2777-2789
29. Asadi, A.; Ajami, D.; Rebek, J., Jr. J. Am. Chem. Soc. 2011, 133 (28) 10682-4
30. Ajami, D.; Rebek, J., Jr. J. Am. Chem. Soc. 2006, 128, 15038-15039
31. Ko, Y. H.; Kim, H.; Kim, Y.; Kim, K. Angew. Chem., Int. Ed. 2008, 47, 4106-4109
32. Baek, K.; Kim, Y.; Kim, H.; Yoon, M.; Hwang, I.; Ko, Y. H.; Kim, K. Chem. Commun. 2010, 4091-4093
33. Ko, Y. H.; Kim, Y.; Kim, H.; Kim, K. Chem.-Asian J. 2011, 6 (2) 652-657
34. Liu, S.; Whisenhunt-Ioup, S. E.; Gibb, C. L. D.; Gibb, B. C. Supramol. Chem. 2011, 24, 480-485
35. Gibb, C. L. D.; Gibb, B. C. J. Am. Chem. Soc. 2004, 126, 11408-11409
36. Cohen, Y.; Avram, L.; Frish, L. Angew. Chem., Int. Ed. 2005, 44, 520-554
37. Ajami, D.; Iwasawa, T.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 2006, 103 (24) 8934-6
38. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley and Sons: New York, 1994.
39. Kuad, P.; Miyawaki, A.; Takashima, Y.; Yamaguchi, H.; Harada, A. J. Am. Chem. Soc. 2007, 129, 12630-12631
40. Liu, Y.; Chen, Y. Acc. Chem. Res. 2006, 39, 681-691
41. Castellano, R. K.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3657-3663
42. Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 898-952
43. Sun, H.; Gibb, C. L. D.; Gibb, B. C. Supramol. Chem. 2008, 20, 141-147
44. Three points suggest that MS analysis of these complexes warrants further study: (1) The relative stability of these and related complexes (see for example: Tang, H.; de Oliveira, C.; Sonntag, G.; Gibb, C. L. D.; Gibb, B. C; Bohne, C. J. Am. Chem. Soc. 2012, 134, 5544-5547) suggests that the decrease in the hydrophobic effect as a result of droplet-size reduction during the ionization process may play a role in the observance of a preponderance of free host; (2) The apparent necessity for sodium ions in the 2:2 complex suggests a possible role of metal ion templation in the larger assemblies; (3) Variations in cluster distributions as a function in sample suggest other yet unappreciated important factors in the MS analysis. Further experiments on these and other complexes will be reported in future communications