A magnesium-selective ionophore containing four amide carbonyl ligands derived from L-tartaric acid and axial furano oxygen binding sites

Journal of Inclusion Phenomena

Volumn 43, Issue 1-2, 2002, Pages 15-18

  Choi, Heung Jin ^a   Lee, Dong Hee ^a   Park, Yeon Sil ^a   Lee, In Kyu ^a   Kim, Young Chul ^a  

^a Kyungpook National University   (South Korea)

Author keywords

Circular dichroism; Ion selective electrode; Magnesium ionophore; NMR titration

Indexed keywords

IONOPHORE; LIGAND; MACROCYCLIC COMPOUND; MAGNESIUM; TARTARIC ACID;

ARTICLE; BINDING SITE; CIRCULAR DICHROISM; COMPLEX FORMATION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TITRIMETRY;

EID: 0142082567     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1020469618610     Document Type: Article

References (30)

1. F. Vögtle and E. Weber: Crown Ethers-Complexes and Selectivity. In S. Patai (ed.), The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and their Sulphur Analogues, John Wiley & Sons, New York (1980), pp. 59-156.
2. E. Graf and J.-M. Lehn: J. Am. Chem. Soc. 97, 5022 (1975).
3. E. Graf and J.-M. Lehn: J. Am. Chem. Soc. 98, 6403 (1976).
4. E. Graf, J.-P. Kintzinger, J.-M. Lehn and J. LeMoigne: J. Am. Chem. Soc. 104, 1672 (1982).
5. T.W. Bell, H.-J. Choi and G. Hiel: Tetrahedron Lett. 34, 971 (1993).
6. H.-J. Choi, M.-O. Kwak and J.-M. Kim: Tetrahedron Lett. 38, 6217 (1997).
7. H.-J. Choi, Y.-H. Kim and M.-O. Kwak: Bull. Korean Chem. Soc. 17, 395 (1996).
8. (a) J.M. Timko and D.J. Cram: J. Am. Chem. Soc. 96, 7159 (1974).
9. (b) J.M. Timko, S.S. Moore, D.M. Walba, P.C. Hiberty and D.J. Cram: J. Am. Chem. Soc. 99, 4207 (1977).
10. (a) C.T. Seto, J.P. Mathias and G.M. Whitesides: J. Am. Chem. Soc. 115, 1321 (1993).
11. (b) P.C. Kearney, L.S. Mizoue, R.A. Kumpf, J.E. Forman, A. McCurdy and D.A. Dougherty: J. Am. Chem. Soc. 115, 9907 (1993).
12. (c) J.S. Bradshaw, S.L. Baxter, J.D. Lamb, R.M. Izatt and J.J. Christensen: J. Am. Chem. Soc. 103, 1821 (1981).
13. H.-J. Choi, M.-O. Kwak and H. Song: Syn. Comm. 27, 1273 (1997).
14. 3) δ 156.0, 106.1, 39.7.
15. 10: C, 55.71; H, 5.75; N, 9.99. Found: C, 55.52; H, 6.01; N, 9.65.
16. 14: C, 55.32; H, 4.99. Found: C, 55.08; H, 5.08.
17. M. V. Rouilly, M. Badertscher, E. Pretsch, G. Suter and W. Simon: Anal. Chem. 60, 2013 (1988).
18. Low-energy conformations were determined by molecular mechanics with Monte Carlo minimization procedures, using the MMFF94 force field as implemented in the Spartan program. The equilibrium geometry for the low energy conformations was calculated at the AM1 level.
19. (a) E. Metzger, D. Ammann, U. Schefer, E. Pretsch and W. Simon: Chimia 38, 440 (1984).
20. (b) E. Metzger, D. Ammann, R. Asper and W. Simon: Anal. Chem. 58, 132 (1986).
21. U. Wuthier, H.V. Pham, R. Zünd, D. Welti, R.J.J. Funck, A. Bezegh, D. Ammann, E. Pretsch and W. Simon: Anal. Chem. 56, 535 (1984).
22. 2+, -2.6.
23. K. Suzuki, K. Watanabe, Y. Matsumoto, M. Kobayashi, S. Sata, D. Siswanta and H. Hisamoto: Anal. Chem. 67, 324 (1995).
24. CD spectra were obtained at 298 K for a series of acetonitrile solutions containing macrocycle 1 (0.125 mM) and varying amounts of magnesium perchlorate (0.10 equiv, 0.25 equiv, 0.50 equiv, 0.75 equiv and 1.00 equiv) in a cell of 1 cm path length.
25. (a) N. Harada, M. Ohashi and K. Nakanishi: J. Am. Chem. Soc. 90, 7349 (1968).
26. (b) N. Harada and K. Nakanishi: J. Am. Chem. Soc. 90, 7351 (1968).
27. (c) N. Harada and K. Nakanishi: J. Am. Chem. Soc. 91, 3989 (1969).
28. (d) N. Harada and K. Nakanishi: Acc. Chem. Res. 5, 257 (1972).
29. T.R. Kelly and M.H. Kim: J. Am. Chem. Soc. 116, 7072 (1994).
30. C.S. Wilcox: In H.-J. Schneider and H. Dürr (ed.), Frontiers in Supramolecular Organic Chemistry and Photochemistry. VCH, Weinheim (1991), pp. 123-143.