New Lariat Ether Carboxylic and Hydroxamic Acids: Synthesis and Lanthanide Ion Complexation

Journal of Heterocyclic Chemistry

Volumn 35, Issue 4, 1998, Pages 875-885

  Elshani, Sadik ^a,b   Noriyuki, Randal ^a   Wai, Chien M ^a   Natale, N R ^a   Bartsch, Richard A ^b  

^a UNIVERSITY OF IDAHO   (United States)

^b TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001347279     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570350416     Document Type: Article

References (54)

1. For recent reviews: [a] G. W. Gokel, Chem. Soc. Rev., 39 (1992); [b] Y. Inoue and G. W. Gokel, Cation Binding by Macrocycles, Marcel Dekker, New York, 1990; R. D. Hancock and A. E. Martell, Chem. Rev., 89, 1875 (1989); R. M. Izatt, K. Pawlak, J. S. Bradshaw and R. L. Bruening, Chem. Rev., 91, 1721 (1991); [e] R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 92, 1261 (1992); [f] R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 95, 2529 (1995); [g] J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu and J. K. Hathaway, Comprehensive Supramolecular Chemistry, Vol l, G. W. Gokel, ed, Pergamon, New York, 1996, p 35.
2. For recent reviews: [a] G. W. Gokel, Chem. Soc. Rev., 39 (1992); [b] Y. Inoue and G. W. Gokel, Cation Binding by Macrocycles, Marcel Dekker, New York, 1990; R. D. Hancock and A. E. Martell, Chem. Rev., 89, 1875 (1989); R. M. Izatt, K. Pawlak, J. S. Bradshaw and R. L. Bruening, Chem. Rev., 91, 1721 (1991); [e] R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 92, 1261 (1992); [f] R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 95, 2529 (1995); [g] J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu and J. K. Hathaway, Comprehensive Supramolecular Chemistry, Vol l, G. W. Gokel, ed, Pergamon, New York, 1996, p 35.
3. For recent reviews: [a] G. W. Gokel, Chem. Soc. Rev., 39 (1992); [b] Y. Inoue and G. W. Gokel, Cation Binding by Macrocycles, Marcel Dekker, New York, 1990; R. D. Hancock and A. E. Martell, Chem. Rev., 89, 1875 (1989); R. M. Izatt, K. Pawlak, J. S. Bradshaw and R. L. Bruening, Chem. Rev., 91, 1721 (1991); [e] R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 92, 1261 (1992); [f] R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 95, 2529 (1995); [g] J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu and J. K. Hathaway, Comprehensive Supramolecular Chemistry, Vol l, G. W. Gokel, ed, Pergamon, New York, 1996, p 35.
4. For recent reviews: [a] G. W. Gokel, Chem. Soc. Rev., 39 (1992); [b] Y. Inoue and G. W. Gokel, Cation Binding by Macrocycles, Marcel Dekker, New York, 1990; R. D. Hancock and A. E. Martell, Chem. Rev., 89, 1875 (1989); R. M. Izatt, K. Pawlak, J. S. Bradshaw and R. L. Bruening, Chem. Rev., 91, 1721 (1991); [e] R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 92, 1261 (1992); [f] R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 95, 2529 (1995); [g] J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu and J. K. Hathaway, Comprehensive Supramolecular Chemistry, Vol l, G. W. Gokel, ed, Pergamon, New York, 1996, p 35.
5. For recent reviews: [a] G. W. Gokel, Chem. Soc. Rev., 39 (1992); [b] Y. Inoue and G. W. Gokel, Cation Binding by Macrocycles, Marcel Dekker, New York, 1990; R. D. Hancock and A. E. Martell, Chem. Rev., 89, 1875 (1989); R. M. Izatt, K. Pawlak, J. S. Bradshaw and R. L. Bruening, Chem. Rev., 91, 1721 (1991); [e] R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 92, 1261 (1992); [f] R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 95, 2529 (1995); [g] J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu and J. K. Hathaway, Comprehensive Supramolecular Chemistry, Vol l, G. W. Gokel, ed, Pergamon, New York, 1996, p 35.
6. For recent reviews: [a] G. W. Gokel, Chem. Soc. Rev., 39 (1992); [b] Y. Inoue and G. W. Gokel, Cation Binding by Macrocycles, Marcel Dekker, New York, 1990; R. D. Hancock and A. E. Martell, Chem. Rev., 89, 1875 (1989); R. M. Izatt, K. Pawlak, J. S. Bradshaw and R. L. Bruening, Chem. Rev., 91, 1721 (1991); [e] R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 92, 1261 (1992); [f] R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 95, 2529 (1995); [g] J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu and J. K. Hathaway, Comprehensive Supramolecular Chemistry, Vol l, G. W. Gokel, ed, Pergamon, New York, 1996, p 35.
7. For recent reviews: [a] G. W. Gokel, Chem. Soc. Rev., 39 (1992); [b] Y. Inoue and G. W. Gokel, Cation Binding by Macrocycles, Marcel Dekker, New York, 1990; R. D. Hancock and A. E. Martell, Chem. Rev., 89, 1875 (1989); R. M. Izatt, K. Pawlak, J. S. Bradshaw and R. L. Bruening, Chem. Rev., 91, 1721 (1991); [e] R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 92, 1261 (1992); [f] R. M. Izatt, K. Pawlak and J. S. Bradshaw, Chem. Rev., 95, 2529 (1995); [g] J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu and J. K. Hathaway, Comprehensive Supramolecular Chemistry, Vol l, G. W. Gokel, ed, Pergamon, New York, 1996, p 35.
8. D. J. Cram, Angew. Chem., Int. Ed, Engl., 27, 1009 (1988).
9. [3a] J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 27, 89 (1988);
10. For reviews of macrocycle complexes with the lanthanide ions; [b] J. C. G. Bunzli and D. Wessner, Coord. Chem. Rev., 10, 191 (1984); J. C. G. Bunzli, Handbook on the Physics and Chemistry of Rare Earths, Vol 9, K. A. Gschneidner, Jr. and L. Eyring, eds, Elsevier, Amsterdam, 1987, p 321; G. A. Adachi and Y. Hirashima, Cation Binding by Macrocycles, Y. Inoue and G. W. Gokel, eds, Marcel Dekker, New York, 1990, p 701; [e] For a review of crown ether and acyclic polyether complexes with the lanthanides and actinides: R. D. Rogers and C. R. Bauer, Comprehensive Supramolccular Chemistry, Vol 1, G. W. Gokel, ed, Pergamon, New York, 1996, p 315; [f] For a comprehensive review on the design and synthesis of marcrocyclic ligands and their complexes with lanthanides and actinides, V. Alexander, Chem. Rev., 95, 273 (1995).
11. For reviews of macrocycle complexes with the lanthanide ions; [b] J. C. G. Bunzli and D. Wessner, Coord. Chem. Rev., 10, 191 (1984); J. C. G. Bunzli, Handbook on the Physics and Chemistry of Rare Earths, Vol 9, K. A. Gschneidner, Jr. and L. Eyring, eds, Elsevier, Amsterdam, 1987, p 321; G. A. Adachi and Y. Hirashima, Cation Binding by Macrocycles, Y. Inoue and G. W. Gokel, eds, Marcel Dekker, New York, 1990, p 701; [e] For a review of crown ether and acyclic polyether complexes with the lanthanides and actinides: R. D. Rogers and C. R. Bauer, Comprehensive Supramolccular Chemistry, Vol 1, G. W. Gokel, ed, Pergamon, New York, 1996, p 315; [f] For a comprehensive review on the design and synthesis of marcrocyclic ligands and their complexes with lanthanides and actinides, V. Alexander, Chem. Rev., 95, 273 (1995).
12. For reviews of macrocycle complexes with the lanthanide ions; [b] J. C. G. Bunzli and D. Wessner, Coord. Chem. Rev., 10, 191 (1984); J. C. G. Bunzli, Handbook on the Physics and Chemistry of Rare Earths, Vol 9, K. A. Gschneidner, Jr. and L. Eyring, eds, Elsevier, Amsterdam, 1987, p 321; G. A. Adachi and Y. Hirashima, Cation Binding by Macrocycles, Y. Inoue and G. W. Gokel, eds, Marcel Dekker, New York, 1990, p 701; [e] For a review of crown ether and acyclic polyether complexes with the lanthanides and actinides: R. D. Rogers and C. R. Bauer, Comprehensive Supramolccular Chemistry, Vol 1, G. W. Gokel, ed, Pergamon, New York, 1996, p 315; [f] For a comprehensive review on the design and synthesis of marcrocyclic ligands and their complexes with lanthanides and actinides, V. Alexander, Chem. Rev., 95, 273 (1995).
13. For reviews of macrocycle complexes with the lanthanide ions; [b] J. C. G. Bunzli and D. Wessner, Coord. Chem. Rev., 10, 191 (1984); J. C. G. Bunzli, Handbook on the Physics and Chemistry of Rare Earths, Vol 9, K. A. Gschneidner, Jr. and L. Eyring, eds, Elsevier, Amsterdam, 1987, p 321; G. A. Adachi and Y. Hirashima, Cation Binding by Macrocycles, Y. Inoue and G. W. Gokel, eds, Marcel Dekker, New York, 1990, p 701; [e] For a review of crown ether and acyclic polyether complexes with the lanthanides and actinides: R. D. Rogers and C. R. Bauer, Comprehensive Supramolccular Chemistry, Vol 1, G. W. Gokel, ed, Pergamon, New York, 1996, p 315; [f] For a comprehensive review on the design and synthesis of marcrocyclic ligands and their complexes with lanthanides and actinides, V. Alexander, Chem. Rev., 95, 273 (1995).
14. For reviews of macrocycle complexes with the lanthanide ions; [b] J. C. G. Bunzli and D. Wessner, Coord. Chem. Rev., 10, 191 (1984); J. C. G. Bunzli, Handbook on the Physics and Chemistry of Rare Earths, Vol 9, K. A. Gschneidner, Jr. and L. Eyring, eds, Elsevier, Amsterdam, 1987, p 321; G. A. Adachi and Y. Hirashima, Cation Binding by Macrocycles, Y. Inoue and G. W. Gokel, eds, Marcel Dekker, New York, 1990, p 701; [e] For a review of crown ether and acyclic polyether complexes with the lanthanides and actinides: R. D. Rogers and C. R. Bauer, Comprehensive Supramolccular Chemistry, Vol 1, G. W. Gokel, ed, Pergamon, New York, 1996, p 315; [f] For a comprehensive review on the design and synthesis of marcrocyclic ligands and their complexes with lanthanides and actinides, V. Alexander, Chem. Rev., 95, 273 (1995).
15. W. J. McDowell, Sep. Sci. Technol., 23, 1251 (1988).
16. [5a] J. Strzelbicki and R. A. Bartsch, Anal. Chem., 53, 1894 (1981);
17. [b] J. Strzelbicki and R. A. Bartsch, Anal. Chem., 53, 2247 (1981);
18. [c] J. Strzelbicki and R. A. Bartsch, Anal. Chem., 53, 2251 (1981);
19. [d] M. J. Pugia, G. Ndip, H. K. Lee, Il-Woo Yang and R. A. Bartsch, Anal. Chem., 58, 2723 (1986);
20. [e] W. Walkowiak, W. A. Charewicz, S. I. Rang, I. W. Yang, M. J. Pugia and R. A. Bartsch, Anal Chem., 62, 2018 (1990);
21. [f] T. Hayashita, M. J. Goo, J. C. Lee, J. S. Kim, J. Krzykawski and R. A. Bartsch, Anal. Chem., 62, 2283 (1990);
22. [g] T. Hayashita, J. J. Lee, S. Chen and R. A. Bartsch, Anal. Chem., 63, 1844 (1991);
23. [h] T. Hayashita, J. H. Lee, J. C. Lee, J. Krzykawski and R. A. Bartsch, Talanta, 39, 857 (1992);
24. [i] T. Hayashita, J. H. Lee, M. G. Hankins, J. C. Lee, J. S. Kim, J. M. Knobeloch and R. A. Bartsch, Anal Chem., 64, 815 (1992).
25. [6a] J. Tang and C. M. Wai, Anal Chem., 58, 3233 (1986);
26. [b] J. Tang and C. M. Wai, Analyst, 114, 451 (1989).
27. [7a] J. Tang and C. M. Wai, Radioanal Nucl. Chem. Letters, 128, 61 (1989);
28. [b] For the separation of thorium from the lanthanides, H. S. Du, D. J. Wood, S. Elshani and C. M. Wai, Talanta, 40, 173 (1993).
29. [8a] L. Bauer and O. Exner, Angew. Chem., Int. Ed. Engl., 13, 376 (1974);
30. [b] B. Chatterjee, Coord. Chem. Rev., 26, 281 (1978).
31. V. Prelog, Pure Appl. Chem., 6, 327 (1963).
32. H. Maehr, Pure Appl Chem., 28, 603 (1971).
33. Y. Sun, A. E. Martell and R. J. Motekaitis, Inorg. Chem., 24, 4343 (1985).
34. Y. Sun and A. E. Martell, J. Am. Chem. Soc., 111, 8023 (1989).
35. Y. Sun and A. E. Martell, Tetrahedron, 46, 2725 (1990).
36. R. J. Motekaitis, Y. Sun and A. E. Martell, Inorg. Chem., 30, 1554 (1991).
37. L. C. Uhlir, P. C. Durbin, N. Jeung and K. N. Raymond, J. Med. Chem., 36, 5041 (1993).
38. J. Xu, S. J. Franklin, D. W. Whisenhunt, Jr. and K. N. Raymond, J. Am. Chem. Soc., 117, 7245 (1995).
39. J. R. Telford and K. N. Raymond, Comprehensive Supramolecular Chemistry, Vol 1, G. W. Gokel, ed, Pergamon, New York, 1996, p 245.
40. D. J. Wood, S. Elshani, H. S. Du, N. R. Natale and C. M. Wai, Anal. Chem., 65, 1350 (1993).
41. R. A. Bartsch, G. S. Heo, S. I. Kang, Y. Liu and J. Strzelbicki, J. Org. Chem., 47, 457 (1982).
42. G. S. Heo, R. A. Bartsch, L. L. Schlobohm and J. G. Lee, J. Org. Chem., 46, 3574 (1981).
43. R. A. Bartsch, V. Liu, S. I. Kang, B. Son, G. S. Heo, P. G. Hipes and L. J. Bills, J. Org. Chem., 48, 4864 (1983).
44. R. H. Jaeger and R. Robinson, Tetrahedron, 14, 320 (1961).
45. [23a] P. J. Maurer and M. S. Miller, J. Am. Chem. Soc., 104, 3096 (1982);
46. [b] Y. Sun and A. E. Martell, J. Am. Chem. Soc., 111, 8023 (1989).
47. E. Lipczynska-Kochany and E. Ewamura, J. Org. Chem., 47, 5277 (1982).
48. D. D. Brown, K. W. Glass, R. Mageswaran and B. Girmay, Mag. Reson. Chem., 26, 970 (1982).
49. N. J. Fitzpatrick and R. Mageswaran, Polyhedron, 8, 2255 (1989).
50. L. Turi, J. J. Dannenberg, J. Rama and O. N. Ventura, J. Phys. Chem., 96, 3709 (1992).
51. J. D. Simon, W. R. Moomaw and T. H. Ceckler, J. Phys. Chem., 89, 5659.
52. J. C. G. Bimzli, H. T. Oanh and B. Gillel, Inorg. Chem. Acta, 53, 2219 (1981).
53. M. J. Pugia, B. E. Knudsen, C. V. Cason and R. A. Bartsch, J. Org. Chem., 52, 541 (1987).
54. G. M. Sheldrick, SHELXTL-Plus Users Manual. Release 4.0, Siemens Analytical Instruments, Madison, Wisconsin, 1990.