Synthesis and Properties of 5-Chloro-8-hydroxyquinoline-Substituted Azacrown Ethers: A New Family of Highly Metal Ion-Selective Lariat Ethers

Inorganic Chemistry

Volumn 35, Issue 25, 1996, Pages 7229-7240

  Bordunov, Andrei V ^a   Bradshaw, Jerald S ^a   Zhang, Xian Xin ^a   Kent Dalley, N ^a   Kou, Xiaolan ^a   Izatt, Reed M ^a  

^a Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001589949     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic9610290     Document Type: Article

References (48)

1. (a) Gatto, V. J.; Gokel, G. W. J. Am. Chem. Soc. 1984, 106, 8240.
2. (b) Gatto, V. J.; Arnold, K. A.; Viscariello, A. M.; Miller, S. R.; Morgan, C. R.; Gokel, G. W. J. Org. Chem. 1986, 51, 5373.
3. (c) Tsukube, H.; Yamashita, K.; Iwaehido, T.; Zenki, M. Tetrahedron Lett. 1989, 30, 3983.
4. (d) Tsukube, H.; Adachi, H.; Morosawa, S. J. Chem. Soc., Perkin Trans. 1 1989, 89.
5. (e) Matsumoto, K.; Minatogawa, H.; Munakata, M.; Toda, M.; Tsukube, H. Tetrahedron Lett. 1990, 31, 3923.
6. (a) Shinkai, S.; Ishikawa, Z.; Shinkai, H.; Tsuno, T.; Makishima, H.; Ueda, K.; Manabe, O. J. Am. Chem. Soc. 1984, 106, 1801.
7. (b) Nishida, H.; Katayama, Y.; Katsuki, H.; Nakamura, H.; Takagi, M.; Ueno, K.; Chem. Lett. 1982, 1853.
8. (c) Sakai, Y.; Kawano, N.; Nakamura, H.; Takagi, M. Talanta 1986, 33, 407.
9. (d) Katayama, Y.; Fukuda, R.; Iwasaki, T.; Nita, K.; Takagi, M. Anal. Chim. Acta 1988, 204, 113.
10. (e) Nakamura H.; Sakka, H.; Takagi, M.; Ueno, K. Chem. Lett. 1981, 1305.
11. (f) Nakamura H.; Nita, K.; Takagi, M.; Ueno, K. Heterocycles 1984, 21, 762.
12. (g) Nishida, H.; Tazaki, M.; Takagi, M.; Ueno, K. Mikrochim. Acta 1981, 1, 281.
13. (h) Shiga, M.; Nishida, H.; Nakamura, M.; Takagi, M.; Ueno, K. Bunseki Kagaku 1983, 32, E293.
14. (i) Katayama, Y.; Fukuda, R.; Takagi, M. Anal. Chim. Acta 1986, 185, 295.
15. (j) Katayama, Y.; Nita, K.; Ueda, M.; Nakamura, H.; Takagi, M. Anal. Chim Acta 1985, 173, 193.
16. For a review, see: McDaniel, C. W.; Bradshaw, J. S.; Izatt, R. M. Heterocycles 1990, 30, 665.
17. (a) Ueno, K.; Imamura, T.; Cheng, K. L. Handbook of Organic Analytical Reagents, 2nd ed.; CRC Press, Inc.: Boca Raton, FL, 1992.
18. (b) Van Veggel, F. C. J. M.; Verboom, W.; Reinhoudt, D. N. Chem. Rev. 1994, 94, 279.
19. (a) Stary, J. The Solvent Extraction of Metal Chelates: Pergamon Press: New York, 1964.
20. (b) Sandell, E. B.; Onishi, H. Photometric Determination of Traces of Metals, 4th ed.; John Wiley & Sons: New York, 1978; p 415.
21. (c) Welcher, F. J. 8-Hydroxyquinoline in Organic Analytical Reagents; Van Nostrand Reinhold: Princeton, NJ, 1947; Vol. 1, p 264.
22. (d) Gordon, L.; Salutsky, M. L.; Willard, H. H. Precipitation from Homogeneous Solution; John Wiley & Sons: New York, 1959.
23. Zhang, X. X.; Bordunov, A. V.; Bradshaw, J. S.; Dalley, N. K.; Kou, X.; Izatt, R. M. J. Am. Chem Soc. 1995, 117, 11507.
24. (a) Lukyanenko, N. G.; Pastushok, V. N.; Bordunov, A. V. Synthesis 1991, 241.
25. (b) Lukyanenko, N. G.; Pastushok, V. N.; Bordunov, A. V.; Vetrogon, V. I.; Vetrogon, N. I., Bradshaw, J. S. J. Chem. Soc., Perkin Trans, 1 1994, 1489.
26. (a) Bogatsky, A. V.; Lukyanenko, N. G.; Pastushok, V. N.; Kostyanovsky, R. G. Dokl. Acad. Nauk SSSR 1982, 265, 619; Chem. Abstr. 1982, 97, 216146.
27. (a) Bogatsky, A. V.; Lukyanenko, N. G.; Pastushok, V. N.; Kostyanovsky, R. G. Dokl. Acad. Nauk SSSR 1982, 265, 619; Chem. Abstr. 1982, 97, 216146.
28. (b) Bogatsky, A. V.; Lukyanenko, N. G.; Pastushok, V. N.; Kostyanovsky, R. G. Synthesis 1983, 992.
29. Weizmann, M.; Bograchov, E. J. Am. Chem. Soc. 1947, 69, 1222.
30. (a) Oscarson, J. L.; Izatt, R. M. In Physical Methods of Chemistry: Determination of Thermodynamic Properties; Rossiter, B. W., Baetzoid, R. C., Eds.; John Wiley & Sons: New York, 1992; Vol. VI, Chapter 7.
31. (b) Izatt, R. M.; Wu, G. Thermochim. Acta 1989, 154, 161-166.
32. (c) Eatough, D. J.; Izatt, R. M.; Christensen, J. J. In Biochemical and Clinical Applications of Thermometric and Thermal Analysis; Jespersen, N. D., Ed.; Elsevier Science: New York, 1982; Chapters 2 and 7.
33. (a) Gatto, V. J.; Arnold, K. A.; Viscariello, A. M.; Miller, S. R.; Gokel, G. W. Tetrahedron Lett. 1986, 27, 327.
34. (b) Buschmann, H.-J. Inorg. Chim. Acta 1986, 125, 31.
35. (c) Buschmann, H.-J. J. Solution Chem. 1986, 15, 453.
36. (c) Buschmann, H.-J. J. Solution Chem. 1986, 15, 453. (d) Buschmann, H.-J. Inorg. Chim. Acta 1985, 108, 241.
37. (e) Kashanian, S.; Shamsipur, M. Inorg. Chim. Acta 1989, 155, 203.
38. (a) Live, D.; Chan, S. I. J. Am. Chem. Soc. 1976, 98, 3769.
39. (b) Takai, Y.; Okumura, Y.; Takahashi, S.; Sawada, M.; Kawamura, M.; Uchiyama, T. J. Chem. Soc. Chem. Commun. 1993, 53.
40. (c) Li, Y.; Echegoyen, L.; Martinez-Diaz, M. V.; de Mendoza, J.; Torres, T. J. Org. Chem. 1991, 56, 4193.
41. (d) Tsukube, H.; Sohmiya, H. J. Org. Chem. 1991, 56, 875.
42. (e) Seel, C.; Vögtle, F. In Perspectives in Coordination Chemistry, Williams, A. F.; Floriani, C.; Merbach, A. E., Eds.; VCH Publishers Inc.: New York, 1992; p 47.
43. (f) Izatt, R. M.; Zhu, C. Y.; Dalley, N. K.; Curtis, J. C.; Kou, X.; Bradshaw, J. S. J. Phys. Org. Chem. 1992, 5, 656.
44. Sanders, J. K. M.; Hunter, B. K. Modern NMR Spectroscopy; Oxford University Press: Oxford, U.K., 1987.
45. Alihodžić, S.; Žinić, M.; Klaić, B.; Kiralj, R.; Kojić-Prodić, B.; Herceg, M.; Cimerman, Z. Tetrahedron Lett. 1993, 34, 8345.
46. Black, D. St. C.; McLean, I. A. Aust. J. Chem. 1971, 24, 1401.
47. International Tables for X-ray Crystallography; Ibers, J. A., Hamilton, W. C., Eds.; Kynoch Press: Birmingham, England, 1974; Vol. 4, p 99.
48. Sheldrick, G. M. SHELXTL-PLUS; Siemens Analytical X-ray Instruments, Inc.: Madison, WI, 1990.