Effect of competing alkali metal cations on neutral host's anion binding ability

Organic Letters

Volumn 2, Issue 20, 2000, Pages 3099-3102

  Shukla, Rameshwer ^a   Kida, Toshiyuki ^a   Smith, Bradley D ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001040238     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0063104     Document Type: Article

References (42)

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13. The carboxylate binding abilities of 1 and related urea derivatives are summarized in Hughes, M. P.; Smith, B. D. J. Org. Chem. 1997, 62, 4492-4501 and references therein.
14. The detailed NMR titration procedures and the subsequent fitting of the data to a 1:1 binding model using nonlinear computer methods are described in ref 7. Dilution studies show that host aggregation is very weak and so can be ignored. A number of other host/salt systems were examined, but they could not be analyzed due to precipitation problems.
15. (a) Swarc M. In Ions and Ion Pairs in Organic Reactions: Swarc, M., Ed.; Wiley: New York. 1972; Vol. 1, Chapter 1.
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22. 9d
23. Reviews that discuss salt-binding hosts: (a) Antonisse, M. M. G.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1998, 443-448.
24. (b) Kimura, E.; Koike, T. J. Chem. Soc., Chem. Commun. 1998, 1495-1500.
25. (c) Stibor I ; Hafeed, D. S. M.; Lhotak, P.; Hodacova, J.; Koca, J.; Cajan, M. Gazz. Chim. Ital. 1997, 127, 673-685.
26. (d) Reetz, M. T. In Comprehensive Supramoleculur Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Lehn, J.-M., Gokel, G. W., Eds.; Pergamon: Oxford, 1996; Vol. 2, pp 553-562. For a recent listing of papers that describe salt binding, see ref 17b.
27. (a) Kubik, S.; Goddard, R. J. Org. Chem. 1999, 64, 9475-9486.
28. (b) Beer, P. D.; Hopkins, P. K.; McKinney, J. D. J. Chem. Soc., Chem. Commun. 1999, 1253-1254.
29. (a) Teramae, N.; Shigemori, K.; Nishizawa, S. Chem. Lett. 1999, 1185-1186.
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32. (d) Tozawa, T.; Misawa, Y.; Tokita S.; Kubo, Y. Tetrahedron Lett. 2000, 41, 5219-5223.
33. While hosts 2-4 were designed to bind contact ion pairs, the host structures have enough flexibility to accommodate solvent-separated ion pairs.
34. For some recent X-ray structures of neutral hosts complexed with solvent-separated ion pairs, see: (a) Levitskaia, T. G.; Bryan, J. C.; Saclebon, R. A.; Lamb, J. D.; Moyer, B. A. J. Am. Chem. Soc. 2000, 122, 554-562.
35. (b) Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201-6207.
36. The syntheses of 1-4 are described in the Supporting Information.
37. The anion binding abilities of 1,3-phthalamides are described in ref 17b.
38. (a) Itai, A.; Toriumi, Y.; Saito, S.; Kagechika, H.; Shudo, K. J. Am. Chem. Soc. 1992, 114, 10649-10650.
39. (b) Krebs, F.; Larsen, M.; Jørgensen, M.; Jensen, P. R.; Bielecki, M.; Schaumburg, K. J. Org. Chem. 1998, 63, 9872-9879. (c) Reference 17b.
40. 20 For example, the aromatic signals in 3 and 4 are significantly upfield compared to analogues that are not N-methylated, indicating that the two aromatic rings in 3 and 4 are cofacial.
41. Factors such as the strength and stoichiometry of the crown ether -metal cation interactions (which depend on the host structures) will also affect the observed cooperativity factors, but it appears with the nonencapsulating crown systems reported here that salt ion-pairing has a dominating role.
42. Steed, J. W.; Junk, P. C. J. Chem. Commun., Dalton Trans. 1999, 2141-2146 and references therein.