Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Diaza-18-crown-6 Ethers Containing Partially-fluorinated Benzyl Sidearms: Effects of Covalently Bonded Fluorine on the Alkali Metal Complexation

  • Chi, Ki-Whan (Department of Chemistry, University of Ulsan) ;
  • Shim, Kwang-Taeg (Department of Chemistry, University of Ulsan) ;
  • Huh, Hwang (Department of Chemistry, University of Ulsan) ;
  • Lee, Uk (Department of Chemistry, Pukyong National University) ;
  • Park, Young-Ja (Department of Chemistry, Sookmyung Women's University)
  • Published : 2005.03.20
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Abstract

The stability constants for the diaza-18-crown-6 ethers 2-6 and alkali metal cations ($Na^+,\;K^+,\;Rb^+\;and\;Cs^+$) were determined using potentiometry in 95% methanol. For each metal ion the stability constants of the partiallyfluorinated ligands 3-6 were larger than that of the non-fluorinated ligand 2, which might reflect an interaction between fluorine atoms and alkali metal cations. The stability constant of the ligand 4 was larger than that of the ligand 5 for each metal cation tested. This finding was also supported by the results of cation-induced chemical shifts in $^1H-,\;^{19}F$-NMR and extraction experiment. The potentiometry and NMR results as well as the X-ray crystal structures revealed that the position and number of fluorine atoms in the benzyl side arms was crucial for the enhanced interaction between a ligand and an alkali metal.

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References

  1. Murray-Rust, P.; Stallings, W. C.; Monti, C. T.; Prestone, R. K.; Glusker, J. P. J. Am. Chem. Soc. 1983, 105, 3206 https://doi.org/10.1021/ja00348a041
  2. Plenio, H.; Diodone, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2175 https://doi.org/10.1002/anie.199421751
  3. Plenio, H.; Diodone, R. J. Am. Chem. Soc. 1996, 118, 356 https://doi.org/10.1021/ja952928a
  4. Plenio, H. Chem. Rev. 1997, 97, 3363 https://doi.org/10.1021/cr970465g
  5. Buschmann, H.-J.; Hermann, J.; Kaupp, M.; Plenio, H. Chem. Eur. J. 1999, 5, 2566 https://doi.org/10.1002/(SICI)1521-3765(19990903)5:9<2566::AID-CHEM2566>3.0.CO;2-3
  6. Habata, Y.; Saeki, T.; Akabori, S.; Zhang, X. X.; Bradshaw, J. S. Chem. Commun. 2000, 1469
  7. Takemura, H.; Kariyazono, H.; Yasutake, M.; Kon, N.; Tani, K.; Sako, K.; Shinmyozu, T.; Inazu, T. Eur. J. Org. Chem. 2000, 141
  8. Takemura, H.; Kon, N.; Kotoku, M.; Nakashima, S.; Otsuka, K.; Yasutake, M.; Shinmyozu, T.; Inazu, T. J. Org. Chem. 2001, 66, 2778 https://doi.org/10.1021/jo0016778
  9. Dietrich, B.; Lehn, J. M.; Sauvage, J. Tetrahedron Lett. 1969, 2899
  10. Lehn, J. M.; Sauvage, J. J. Chem. Soc., Chem. Comm. 1971, 440
  11. Lehn, J. M.; Sauvage, J. J. Am. Chem. Soc. 1975, 97, 6700 https://doi.org/10.1021/ja00856a018
  12. Nakatsuji, Y.; Nakayama, T.; Okahara, M.; Dishong, D. M.; Gokel, G. W. Tetrahedron Lett. 1982, 23, 1351 https://doi.org/10.1016/S0040-4039(00)87102-6
  13. Fronczok, F. R.; Gatto, V. J.; Schultz, R. A.; Jungk, S. J.; Colucci, W. J.; Grandour, R. D.; Gokel, G. W. J. Am. Chem. Soc. 1983, 105, 6717 https://doi.org/10.1021/ja00360a031
  14. Echegoyen, L.; Kafifer, A.; Durst, H.; Schultz, R. A.; Ishong, D. M.; Goli, D. M.; Gokel, G. W. J. Am. Chem. Soc. 1984, 106, 5100 https://doi.org/10.1021/ja00330a011
  15. Izatt, R. M.; Pawlak, K.; Bradshaw, J. S. Chem. Rev. 1995, 95, 2529 https://doi.org/10.1021/cr00039a010
  16. Comprehensive Supramolecular Chemistry; Gokel, G. W., Ed; Elsevier: Oxford, 1996; Vol. 1
  17. Su, N.; Bradshaw, J. S.; Zhang, X. X.; Izatt, R. M. J. Org. Chem. 1999, 64, 8855 https://doi.org/10.1021/jo991081o
  18. Zhang, X. X.; Bordunov, A. V.; Bradshaw, J. S.; Dalley, N. K.; Kou, X.-L.; Izatt, R. M. J. Am. Chem. Soc. 1995, 117, 11507 https://doi.org/10.1021/ja00151a014
  19. Elshani, S.; Kobzar, E.; Bartsch, R. A. Tetrahedron 2000, 56, 3291 https://doi.org/10.1016/S0040-4020(00)00248-9
  20. Bordunov, A. V.; Bradshaw, J. S.; Zhang, X. X.; Dalley, N. K.; Kou, X.; Izatt, R. M. Inorg. Chem. 1996, 35, 7229 https://doi.org/10.1021/ic9610290
  21. Izatt, R. M.; Pawlak, K.; Bradshaw, J. S. Chem. Rev. 1991, 91, 1721 https://doi.org/10.1021/cr00008a003
  22. Cation Binding by Macrocycles; Inoue, Y.; Gokel, G. W., Eds; Marcel Dekker, Inc.: New York and Basel, 1990
  23. Connors, K. A. Binding Constants: The Measurement of Molecular Complex Stability; John Wiley and Sons: New York, 1987; pp 21-27
  24. Martell, A. E.; Motekaitis, R. J. The Determination and Use of Stability Constant; VCH: Texas A & M University, USA, 1988
  25. STOE STAD14, X-RED & X-SHAPE, X-ray structure evaluation package; STOE-Cie GMbh: Hilpertstrase 10, D64295, Darmstadt, Germany, 1996
  26. Sheldrick, G. M. Acta Cryst. 1990, A46, 467
  27. Sheldrick, G. M. SHELXS97-2 and SHELXL97-2; University of Gottingen: Gottingen, Germany, 1997

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