Abstract
Incorporation into a 20-crown-6 of a bulky substituent capable of impeding cation/anion access to one face of the crown ether cavity is shown to afford compounds exhibiting good extraction selectivity for potassium ion over both alkaline earth cations (Ca2+, Sr2+) and other alkali metal ions (Na+, Cs+), an apparent result of diminished flexibility of the crown ether cavity, inhibition of the formation of extractable “sandwich” complexes with large cations, and the destabilizing effect of forcing charge-neutralizing counter anions to approach from one face of the crown cavity.
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References
A. H. Bond, M. L. Dietz, R. D. Rogers (Eds), Metal Ion Separation and Preconcentration: Progress and Opportunities, American Chemical Society, Washington, DC, 1999.
R. M. Izatt, J. S. Bradshaw, S. A. Nielsen, J. D. Lamb, J. J. Christensen, Chem. Rev., 85 (1985) 271.
R. M. Izatt, K. Pawlak, J. S. Bradshaw, R. L. Bruening, Chem. Rev., 91 (1991) 1721.
R. M. Izatt, K. Pawlak, J. S. Bradshaw, R. L. Bruening, Chem. Rev., 95 (1995) 2529.
E. P. Kyba, J. M. Timko, L. J. Kaplan, F. DeJong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc., 100 (1978) 4555.
L. R. Sousa, G. D. Y. Sogah, D. M. Hoffman, D. J. Cram, J. Am. Chem. Soc., 100 (1978) 4569.
C. B. Knobler, F. C. A. Gaeta, D. J. Cram, J. Am. Chem. Soc., 110 (1988) 330.
K. Suzuki, H. Yamada, K. Sato, K. Watanabe, H. Hisamoto, Y. Tobe, K. Kobiro, Anal. Chem., 65 (1993) 3404.
K. Suzuki, K. Sato, H. Hisamoto, D. Siswanta, K. Hayashi, N. Kasahara, K. Watanabe, N. Yamamoto, H. Sasakura, Anal. Chem., 68 (1996) 208.
W. E. Bachmann, L. B. Scott, J. Am. Chem. Soc., 70 (1948) 1458.
J. M. Photis, L. A. Paquette, Org. Synth., 57 (1988) 53.
D. N. Reinhoudt, R. T. Gray, C. J. Smith, I. Veenstra, Tetrahedron, 32 (1976) 1161.
E. P. Horwitz, M. L. Dietz, D. E. Fisher, Solv. Extr. Ion Exch., 8 (1990) 199.
J. M. Lehn, J. P. Sauvage, J. Am. Chem. Soc., 97 (1975) 6700.
M. Ouchi, Y. Inoue, T. Kanzaki, T. Hakushi, J. Org. Chem., 49 (1984) 1408.
Y. Inoue, M. Ouchi, T. Hakushi, Bull. Chem. Soc. Japan, 58 (1985) 525.
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Gatrone, R.C., Dietz, M.L., Mitchell, C.D. et al. Steric effects as a basis for improved monovalent cation extraction selectivity in crown ethers. Journal of Radioanalytical and Nuclear Chemistry 258, 673–676 (2003). https://doi.org/10.1023/B:JRNC.0000011768.52925.d0
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DOI: https://doi.org/10.1023/B:JRNC.0000011768.52925.d0