Novel dual-host approach in ion pair extraction: A simple tripodal nitrate host facilitates CsNO3 transfer to 1,2-dichloroethane by a large crown ether

Chemical Communications

Volumn , Issue 3, 2000, Pages 187-188

  Kavallieratos, Konstantinos ^a   Sachleben, Richard A ^a   Van Berkel, Gary J ^a   Moyer, Bruce A ^a  

^a OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICHLOROETHANE; AMIDE; BENZENE DERIVATIVE; CESIUM; CROWN ETHER; NITRATE;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; EXTRACTION; ION PAIR EXTRACTION; MASS SPECTROMETRY; NUCLEAR WASTE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0034615097     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908562i     Document Type: Article

References (48)

1. B. Dietrich, P. Viout and J.-M. Lehn, Macrocyclic Compounds Chemistry, Aspects of Organic and Inorganic Supramolecular Chemistry, VCH, Weinheim, 1992.
2. The Supramolecular Chemistry of Anions, ed. A. Bianchi, K. Bowman-James and E. García-España, Wiley-VCH, New York, 1997; J. L. Atwood, K. T. Holman and J. W. Steed, Chem. Commun., 1996, 1401;
3. The Supramolecular Chemistry of Anions, ed. A. Bianchi, K. Bowman-James and E. García-España, Wiley-VCH, New York, 1997; J. L. Atwood, K. T. Holman and J. W. Steed, Chem. Commun., 1996, 1401;
4. F. P. Schmidtchen and M. Berger, Chem. Rev., 1997, 97, 1609.
5. M. T. Reetz, in Comprehensive Supramolecular Chemistry, ed. F. Vögtle, Pergamon, Oxford, 1996, vol. 2, pp. 553-562.
6. (a) Science and Technology for Disposal of Radioactive Tank Wastes, ed. W. W. Schultz and N. J. Lombardo, Plenum, New York, 1998;
7. (b) C. F. Mason, Biology of Freshwater Pollution, 2nd edn., Longman, New York, 1991.
8. (a) W. J. McDowell, Sep. Sci. Technol., 1988, 23, 1251. For calixarene complexants see:
9. (b) C. D. Gutsche, Calixarenes Revisited, The Royal Society of Chemistry, Cambridge, 1998, ch. 7, pp. 185-208.
10. Y. Marcus, M. J. Kamlet and R. W. Taft, J. Phys. Chem., 1988, 92, 3613.
11. (a) B. A. Moyer, in Comprehensive Supramolecular Chemistry, ed. G. W. Gokel, Pergamon, Oxford, 1996, vol. 1, pp. 401-405;
12. (b) B. A. Moyer and P. V. Bonnesen, in The Supramolecular Chemistry of Anions, ed. A. Bianchi, K. Bowman-James and E. García-España, Wiley-VCH, New York, 1997, pp. 31-33.
13. F. Hofmeister, Arch. Exp. Pathol. Pharmakol., 1888, 24, 247.
14. Y. Marcus, Solvent Extr. Ion Exch., 1989, 7, 567; E. P. Horwitz, M. L. Dietz and D. E. Fisher, Solvent Extr. Ion Exch., 1990, 8, 199; 1991, 9, 1; B. K. Tait and D. P. Shillington, Solvent Extr. Ion Exch., 1993, 11, 877; P, V. Bonnesen, T. J. Haverlock, N. L. Engle, R. A. Sachleben and B. A. Moyer, in Calixarene Molecules for Separations, The American Chemical Society, Washington, DC, in press.
15. Y. Marcus, Solvent Extr. Ion Exch., 1989, 7, 567; E. P. Horwitz, M. L. Dietz and D. E. Fisher, Solvent Extr. Ion Exch., 1990, 8, 199; 1991, 9, 1; B. K. Tait and D. P. Shillington, Solvent Extr. Ion Exch., 1993, 11, 877; P, V. Bonnesen, T. J. Haverlock, N. L. Engle, R. A. Sachleben and B. A. Moyer, in Calixarene Molecules for Separations, The American Chemical Society, Washington, DC, in press.
16. Y. Marcus, Solvent Extr. Ion Exch., 1989, 7, 567; E. P. Horwitz, M. L. Dietz and D. E. Fisher, Solvent Extr. Ion Exch., 1990, 8, 199; 1991, 9, 1; B. K. Tait and D. P. Shillington, Solvent Extr. Ion Exch., 1993, 11, 877; P, V. Bonnesen, T. J. Haverlock, N. L. Engle, R. A. Sachleben and B. A. Moyer, in Calixarene Molecules for Separations, The American Chemical Society, Washington, DC, in press.
17. Y. Marcus, Solvent Extr. Ion Exch., 1989, 7, 567; E. P. Horwitz, M. L. Dietz and D. E. Fisher, Solvent Extr. Ion Exch., 1990, 8, 199; 1991, 9, 1; B. K. Tait and D. P. Shillington, Solvent Extr. Ion Exch., 1993, 11, 877; P, V. Bonnesen, T. J. Haverlock, N. L. Engle, R. A. Sachleben and B. A. Moyer, in Calixarene Molecules for Separations, The American Chemical Society, Washington, DC, in press.
18. Y. Marcus, Solvent Extr. Ion Exch., 1989, 7, 567; E. P. Horwitz, M. L. Dietz and D. E. Fisher, Solvent Extr. Ion Exch., 1990, 8, 199; 1991, 9, 1; B. K. Tait and D. P. Shillington, Solvent Extr. Ion Exch., 1993, 11, 877; P, V. Bonnesen, T. J. Haverlock, N. L. Engle, R. A. Sachleben and B. A. Moyer, in Calixarene Molecules for Separations, The American Chemical Society, Washington, DC, in press.
19. Related work in a collaboration led by K. Bowman-James at the University of Kansas uses receptors derived from N,N,N-tris(aminoethyl)amine; K. Kavallieratos, R. A. Sachleben, J. C. Bryan, B. A. Moyer, A. M. Danby and K. Bowman-James, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 1999;
20. K. Kavallieratos, A. M. Danby, G. J. Van Berkel, M. A. Kelly, R. A. Sachleben, B. A. Moyer and K. Bowman-James, manuscript in preparation.
21. F. de Jong and H. C. Visser, in Comprehensive Supramolecular Chemistry, ed. D. N. Reinhoudt, Pergamon, Oxford, 1996, vol. 10, pp. 13-51; L. A. J. Chrisstoffels, PhD Thesis, University of Twente, 1998.
22. F. de Jong and H. C. Visser, in Comprehensive Supramolecular Chemistry, ed. D. N. Reinhoudt, Pergamon, Oxford, 1996, vol. 10, pp. 13-51; L. A. J. Chrisstoffels, PhD Thesis, University of Twente, 1998.
23. (a) P. Bisson, V. Lynch, M. K. C. Monahan and E. V. Anslyn, Angew. Chem., Int. Ed. Engl., 1997, 36, 2340;
24. (b) R. Jagessar and D. H. Burns, Chem. Commun., 1997, 1685;
25. (c) M. Staffilani, K. S. B. Hancock, J. W. Steed, K. T. Holman, J. L. Atwood, R. K. Juneja and R. S. Burkhalter, J. Am. Chem. Soc., 1997, 119, 6324;
26. (d) R. D. Schnebeck, E. Freisinger and B. Lippert, Angew. Chem., Int. Ed., 1999, 38, 168;
27. (e) P. D. Beer, M. G. B. Drew, D. Hesek and R. Jagessar, J. Chem. Soc., Chem. Commun., 1995, 1187;
28. (f) S. Mason, T. Clifford, L. Seib, K. Kuczera and K. Bowman-James, J. Am. Chem. Soc., 1998, 120, 8899;
29. (g) G. Y. S. Chan, M. G. B. Drew, M. J. Hudson, N. S. Isaacs, P. Byers and C. Madic, Polyhedron, 1996, 15, 3385;
30. (h) R. J. Motekaitis, A. E. Martell, J.-M. Lehn and E.-I. Watanabe, Inorg. Chem., 1982, 21, 4253.
31. 1H NMR prior to extraction.
32. Y. Morzherin, D. M. Rudkevich, W. Verboom and D. N. Reinhoudt, J. Org. Chem., 1993, 58, 7602; C. Seel and F. Vögtle, Angew. Chem., Int. Ed. Engl., 1992, 104, 542.
33. Y. Morzherin, D. M. Rudkevich, W. Verboom and D. N. Reinhoudt, J. Org. Chem., 1993, 58, 7602; C. Seel and F. Vögtle, Angew. Chem., Int. Ed. Engl., 1992, 104, 542.
34. A. P. Davis, J. J. Perry and R. P. Williams, J. Am. Chem. Soc., 1997, 119, 1793.
35. (a) K. Kavallieratos, S. R. de Gala, D. J. Austin and R. H. Crabtree, J. Am. Chem. Soc., 1997, 119, 2325;
36. (b) K. Kavallieratos, C. M. Bertao and R. H. Crabtree, J. Org. Chem., 1999, 64, 1675.
37. E. Fan, S. A. van Arman, S. Kincaid and A. D. Hamilton, J. Am. Chem. Soc., 1993, 115, 369.
38. C. J. Pedersen, J. Am. Chem. Soc., 1967, 89, 7017.
39. R. A. Sachleben, Y. Deng, D. R. Bailey and B. A. Moyer, Solvent. Extr. Ion Exch., 1996, 14, 995; R. A. Sachleben, Y. Deng and B. A. Moyer, Sep. Sci. Technol., 1997, 32, 275.
40. R. A. Sachleben, Y. Deng, D. R. Bailey and B. A. Moyer, Solvent. Extr. Ion Exch., 1996, 14, 995; R. A. Sachleben, Y. Deng and B. A. Moyer, Sep. Sci. Technol., 1997, 32, 275.
41. Y. Deng, R. A. Sachleben and B. A. Moyer, J. Chem. Soc., Faraday Trans., 1995, 4215; T. G. Levitskaia, J. C. Bryan, R. A. Sachleben, J. D. Lamb and B. A. Moyer, J. Am. Chem. Soc., in press.
42. Y. Deng, R. A. Sachleben and B. A. Moyer, J. Chem. Soc., Faraday Trans., 1995, 4215; T. G. Levitskaia, J. C. Bryan, R. A. Sachleben, J. D. Lamb and B. A. Moyer, J. Am. Chem. Soc., in press.
43. + was determined by gamma scintillation.
44. KaleidaGraph, Version 3.0.2. Synergy Software (PCS Inc.), Reading, PA 19606. Developed by Abelbeck Software Inc.
45. K. A. Connors, Binding Constants, Wiley, New York, 1987.
46. J. S. Brodbelt and D. V. Dearden, in Comprehensive Supramolecular Chemistry, ed. J. E. D. Davies and J. A. Ripmeester, Pergamon, Oxford, 1996, vol. 8, ch. 14, pp. 567-589 and references therein.
47. - ion is under investigation.
48. - complexes. Probable aggregation of R or formation of R·crown complexes would be expected to reduce the enhancement and to be stronger for 1 than for 2.