Ammonium ion binding with pyridine-containing crown ethers

Organic Letters

Volumn 2, Issue 19, 2000, Pages 2947-2950

  Chang, Theresa ^a   Heiss, Aaron M ^a   Cantrill, Stuart J ^a   Fyfe, Matthew C T ^a   Pease, Anthony R ^a   Rowan, Stuart J ^a   Stoddart, J Fraser ^a   White, Andrew J P ^b   Williams, David J ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000650979     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0061889     Document Type: Article

References (23)

1. Fyfe, M. C. T.; Stoddart, J. F. Adv. Supramol Chem. 1999, 5, 1-53.
2. Ashton, P. R.; Baxter, I.; Cantrill, S. J.; Fyfe, M. C. T.; Clink, P. T.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. 1998, 37, 1294-1297.
3. (a) Ashton, P. R.; Bartsch, R. A.; Cantrill, S. J.; Hanes, R. E., Jr.; Hickingbottom, S. K.; Lowe, J. N.; Preece, J. A.; Stoddart, J. F.; Talanov, V. S.; Wang, Z.-H. Tetrahedron Lett. 1999, 40, 3661-3664.
4. (b) Cantrill, S. J.; Fulton, D. A.; Heiss, A. M.; Pease, A. R.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 2000, 6, 2274-2287.
5. (c) Bryant, W. S.; Guzei, I. A.; Reingold, A. L.; Merola, J. S.; Gibson, H. W. J. Org. Chem. 1998, 63, 7634-7639.
6. Newcomb, M.; Timko, J. M.; Walba, D. M.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6392-6398.
7. Czekalla, M.; Stephan, H.; Habermann, B.; Trepte, J.; Gloe, K.; Schmidtchen, F. P. Thermochim. Acta 1998, 137-144.
8. Uiterwijk, J. W. H. M.; van Staveren, C. J.; Reinhoudt, D. N.; den Hertog, H. J., Jr.; Kruise, L.; Harkema, S. J. Org. Chem. 1986, 51, 1575-1587.
9. Bradshaw, J. S.; Izatt, R. M. Acc. Chem. Res. 1997, 30, 338-345.
10. For example, the binding of various crown ethers of [18]crown-6 constitution to glycine has been investigated. At 25°C in MeOH, the binding of glycine to pyrido[18]crown-6 was found to be five times larger than that of [18]crown-6. See ref 5.
11. Kamlet, M. J.; Abbout, J. L. Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887.
12. 6 can be found in the Supporting Information.
13. o|), 2θ ≤ 120°] and 289 parameters.
14. + (m/z 419) were observed by FABMS.
15. 1H NMR time scale under identical conditions.
16. 6/DB24C8 complexes display the peak corresponding to the resonance of the methylene protons next to the ammonium center (in both pseudorotaxanes and rotaxanes) as a singlet when unbound and a multiplet when encircled by DB24C8. The same phenomenon is observed when DP24C8 is used as the macrocyclic component.
17. Connors, K. A. Binding Constants; Wiley: New York, 1987.
18. 6 exhibits a similar, but much less dramatic, concentration dependence.
19. 3CN, 1 mM, 235 K). Ashton, P. R.; Chrystal, E. J. T.; Glink, P. T.; Menzer, S.; Schiavo, C.; Spencer, N.; Stoddart, J. F.; Tasker, P. A.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1996, 2, 709-728.
20. + (m/z 732) in addition to the protonated free crown ether (m/z 419).
21. Rowan, S. J.; Cantrill, S. J.; Stoddart, J. F. Org. Lett. 1999, 1, 129-132.
22. + (m/z 892) was also observed, probably arising as a consequence of fragmentation and decomplexation of the crown ether from around the dumbbell.
23. o|), 2θ ≤ 120°] and 984 parameters.