Lariat ether carboxylic acids, O-benzylhydroxamates and hydroxamic acids with fluorinated substituents: Synthesis, metal ion complexation and solubility in supercritical carbon dioxide

Tetrahedron

Volumn 56, Issue 27, 2000, Pages 4651-4657

  Elshani, Sadik ^a,b   Du, Hongshan ^a   Laintz, Kenneth E ^a   Natale, Nicholas R ^a   Wai, Chien M ^a   Elkarim, Nazar S A ^b   Bartsch, Richard A ^b  

^a UNIVERSITY OF IDAHO   (United States)

^b TEXAS TECH UNIVERSITY   (United States)

Author keywords

Complexation; Crown ethers; Solvents and solvent effects; Substituent effects

Indexed keywords

CARBON DIOXIDE; CARBOXYLIC ACID DERIVATIVE; CHLOROFORM; FLUORINE; HYDROXAMIC ACID DERIVATIVE; METAL ION;

ARTICLE; COMPLEX FORMATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SOLUBILITY; SYNTHESIS;

EID: 0034733533     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00380-X     Document Type: Article

References (38)

1. For reviews on lariat ethers, their cation complexation properties and applications, see: (a) Gokel, G. W.; Trafton, J. E. In Cation Binding by Macrocycles; Inoue, Y., Gokel, G. W., Eds.; Marcel Dekker: New York, 1990; pp 253-310. (b) Gokel, G. W. Chem. Soc. Rev. 1992, 39. (c) Gokel, G. W.; Schall, O. F. In Comprehensive Supramolecular Chemistry; Gokel, G. W., Ed.; Pergamon: New York, 1996; Vol. 1, pp 97-152.
2. For reviews on lariat ethers, their cation complexation properties and applications, see: (a) Gokel, G. W.; Trafton, J. E. In Cation Binding by Macrocycles; Inoue, Y., Gokel, G. W., Eds.; Marcel Dekker: New York, 1990; pp 253-310. (b) Gokel, G. W. Chem. Soc. Rev. 1992, 39. (c) Gokel, G. W.; Schall, O. F. In Comprehensive Supramolecular Chemistry; Gokel, G. W., Ed.; Pergamon: New York, 1996; Vol. 1, pp 97-152.
3. For reviews on lariat ethers, their cation complexation properties and applications, see: (a) Gokel, G. W.; Trafton, J. E. In Cation Binding by Macrocycles; Inoue, Y., Gokel, G. W., Eds.; Marcel Dekker: New York, 1990; pp 253-310. (b) Gokel, G. W. Chem. Soc. Rev. 1992, 39. (c) Gokel, G. W.; Schall, O. F. In Comprehensive Supramolecular Chemistry; Gokel, G. W., Ed.; Pergamon: New York, 1996; Vol. 1, pp 97-152.
4. (a) McDaniel, C. W.; Bradshaw, J. S.; Izatt, R. M. Heterocycles 1990, 30, 665.
5. (b) Bradshaw, J. S. J. Incl. Phenom. Mol. Recognit. Chem. 1997, 29, 221.
6. McDowell W.J. Sep. Sci. Technol. 23:1988;1251.
7. Bartsch R.A., Heo G.S., Kang S.I., Liu Y., Strzelbicki J. J. Org. Chem. 47:1982;457.
8. Bartsch R.A., Liu Y., Kang S.I., Son B., Heo G.S., Hipes P.G., Bills L.J. J. Org. Chem. 48:1983;4864.
9. Elshani S., Noriyuki R., Wai C.M., Natale N.R., Bartsch R.A. J. Heterocycl. Chem. 35:1998;875.
10. Strzelbicki J., Bartsch R.A. Anal. Chem. 53:1981;1894.
11. Strzelbicki J., Bartsch R.A. Anal. Chem. 53:1981;2247.
12. Strzelbicki J., Bartsch R.A. Anal. Chem. 53:1981;2251.
13. Pugia M.J., Ndip G., Lee H.K., Yang I.-W., Bartsch R.A. Anal. Chem. 58:1986;2723.
14. Walkowiak W., Charewicz W.A., Kang S.I., Yang I.-W., Pugia M.J., Bartsch R.A. Anal. Chem. 62:1990;2018.
15. Hayashita T., Goo M.J., Lee J.C., Kim J.S., Krzykawski J., Bartsch R.A. Anal. Chem. 62:1990;2283.
16. Hayashita T., Lee J.H., Chen S., Bartsch R.A. Anal. Chem. 63:1991;1844.
17. Hayashita T., Lee J.H., Lee J.C., Krzykawski J., Bartsch R.A. Talanta. 39:1992;857.
18. Hayashita T., Lee J.H., Hankins M.G., Lee J.C., Kim J.S., Knobeloch J.M., Bartsch R.A. Anal. Chem. 64:1992;815.
19. Tang J., Wai C.M. Anal. Chem. 58:1986;3233.
20. Tang J., Wai C.M. Analyst. 114:1989;451.
21. Tang J., Wai C.M. J. Membr. Sci. 35:1988;339.
22. Tang J., Wai C.M. J. Radioanal. Nucl. Chem. Lett. 128:1988;61.
23. Wood D.J., Elshani S., Du H.S., Natale N.R., Wai C.M. Anal. Chem. 65:1993;1350.
24. Laintz K.E., Wai C.M., Yonker C.R., Smith R.D. J. Supercrit. Fluids. 4:1991;194.
25. Laintz K.E., Yu J.J., Wai C.M. Anal. Chem. 64:1992;311.
26. Laintz K.E., Wai C.M., Yonker C.R., Smith R.D. Anal. Chem. 64:1992;2875.
27. Wai C.M., Lin Y., Brauer R.D., Wang S., Beckert W.F. Talanta. 40:1993;1325.
28. Liu Y., Lopez-Avila V., Alcaraz M., Beckert W.F. J. High Resolut. Chromatogr. 16:1993;106.
29. Lin Y., Brauer R.D., Laintz K.E., Wai C.M. Anal. Chem. 65:1993;2549.
30. Lin Y., Wai C.M., Jean F.M., Brauer R.D. Environ. Sci. Technol. 28:1994;1190.
31. Lin Y., Smart N.G., Wai C.M. Environ. Sci. Technol. 29:1995;2706.
32. Stahl E., Schliz W., Schülz E., Willing E. Angew. Chem. Int. Ed. Engl. 17:1978;731.
33. Kimura K., Shono T. Inoue Y., Gokel G., Cation Binding by Macrocycles. 1990;429-464 Marcel Dekker, New York.
34. Ohki A., Lu J.-P., Bartsch R.A. Anal. Chem. 66:1994;651.
35. Bartsch R.A., Lu J.-P., Ohki A. J. Inclusion Phenom. Mol. Recognit. Chem. 32:1998;133.
36. Cram D.J., Trueblood K.N. Vögtle F., Weber E., Host Guest Complex Chemistry. 1985;125-128 Springer, New York.
37. Mok W.M., Shah N.K., Wai C.M. Anal. Chem. 58:1986;110.
38. Recommendations for nomenclature of ion-selective electrodes, Pure Appl. Chem. 1976, 48, 127.