Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Selective Recognition of Dihydrogen Phosphate by Urea-Anthraquinone

  • Jeon, Seung-Won (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Park, Duck-Hee (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Hyo-Kyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Park, Jin-Young (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kang, Sung-Ok (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Nam, Kye-Chun (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • Published : 2003.10.20
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Abstract

A neutral ligand is synthesized and studied for the binding properties with anions by electrochemical methods. The binding of 1,8-bis[(N'-phenylureido)ethyloxy]anthraquinone (BPUA) with $H_2PO_4^-$ makes cathodic shift of its electrochemical potentials and red shift of absorption band. This novel neutral anion receptor BPUA binds anions through hydrogen bonding and show high selectivity with $H_2PO_4^-$ over $CH_3CO_2^-,CI^-,{\;}and{\;}HSO_4^-$. The selecivity of H_2PO_4^-$ over $CH_3CO_2^-,CI^-,{\;}and{\;}HSO_4^-$ may be attributed to the stronger hydrogen bonding with urea moiety and also with anthraquinone moiety of BPUA receptor, and also the higher complementarity of the cavity of BPUA for tetrahedral H_2PO_4^-$.

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References

  1. Jagessar, R. C.; Shang, M.; Scheidt, W. R.; Burns, D. H. J. Am.Chem. Soc. 1998, 120, 11684. https://doi.org/10.1021/ja982052i
  2. Kanyo, Z. F.; Christianson, D. W. J. Biol. Chem. 1991, 266,4264.
  3. Atwood, J. L.; Holman, K. T.; Steed, J. W. Chem. Comm. 1996,1401.
  4. Beer, P. D.; Chen, Z.; Goulden, A. J.; Graydon, A.; Stokes, A. E.;Wear, T. J. Chem. Soc., Chem. Commun. 1993, 1834.
  5. Gale, P. A.; Chen, Z.; Drew, M. G. B.; Heath, J. A.; Beer, P. D.Polyhedron 1998, 17, 405. https://doi.org/10.1016/S0277-5387(97)00389-6
  6. Beer, P. D.; Cadman, J.; Lloris, J. M.; Martinez-Manez, R.;Padiila, M. E.; Pardo, T.; Smith, D. K.; Soto, J. J. Chem. Soc.,Dalton Trans. 1999, 127.
  7. Beer, P. D.; Chen, Z.; Drew, M. G. B.; Johnson, A. O. M.; Smith,D. K.; Spensor, P. Inorg. Chim. Acta 1996, 246, 143 https://doi.org/10.1016/0020-1693(96)05061-X
  8. Yeo, W.-S.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 8137. https://doi.org/10.1016/S0040-4039(98)01806-1
  9. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y.Tetrahedron 1997, 53, 1647. https://doi.org/10.1016/S0040-4020(96)01094-0
  10. Nishizawa, S.; Buhlmann, P.; Iwao, M.; Umezawa, Y. TetrahedronLett. 1995, 36, 6483. https://doi.org/10.1016/0040-4039(95)01296-T
  11. Fan, E.; Arman, S. A. V.; Kincaid, S,; Hamilton, A. D. J. Am.Chem. Soc. 1993, 115, 369. https://doi.org/10.1021/ja00054a066
  12. Sasaki, S.-i.; Mizuno, M.; Naemura, K.; Tobe, Y. J. Org. Chem.2000, 65, 275. https://doi.org/10.1021/jo991237k
  13. Lee, C. L.; Lee, D. H.; Hong, J.-I. Tetrahedron Lett. 2001, 42,8665. https://doi.org/10.1016/S0040-4039(01)01876-7
  14. Scheerder, J.; Fochi, M.; Engbersen, J. F. L.; Reinhoudt, D. N. J.Org. Chem. 1994, 59, 7815. https://doi.org/10.1021/jo00104a044
  15. Scheerder, J.; Engbersen, J. F. L.; Casnati, A.; Ungaro, R.;Reinhoudt, D. N. J. Org. Chem. 1995, 60, 6448. https://doi.org/10.1021/jo00125a035
  16. Fan, E.; Van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am.Chem. Soc. 1993, 115, 369. https://doi.org/10.1021/ja00054a066
  17. Chung, T. D.; Choi, D.; Kang, S. K.; Lee, S. K.; Chang, S. K.;Kim, H. J. Electroanal. Chem. 1995, 396, 431. https://doi.org/10.1016/0022-0728(95)04112-2
  18. Chung, T. D.; Kang, S. K.; Kim, H. S.; Kim, H. J. Electroanal.Chem. 1997, 438, 71. https://doi.org/10.1016/S0022-0728(97)00100-9
  19. Gomez-Kaiter, M.; Reddy, P. A.; Gutsche, C. D.; Echegoyen, L. J.Am. Chem. Soc. 1994, 116, 3580. https://doi.org/10.1021/ja00087a051
  20. Nam, K. C.; Kang, S. O.; Jeong, H. S.; Jeon, S. Tetrahedron Lett.1999, 40, 7343. https://doi.org/10.1016/S0040-4039(99)01505-1
  21. Jeong, H. S.; Choi, E. M.; Kang, S. O.; Nam, K. C.; Jeon, S. J. ofElectroanal. Chem. 2000, 485(2), 154. https://doi.org/10.1016/S0022-0728(00)00108-X
  22. Gustowski, D. A.; Delagdo, M.; Gatto, V. J.; Echegoyen, L.;Gokel, G. W. Tetrahedron Lett. 1986, 27, 3487. https://doi.org/10.1016/S0040-4039(00)84829-7
  23. Delagdo, M.; Echegoyen, L.; Gatto, V. J.; Gustowski, D. A.;Gokel, G. W. J. Am. Chem. Soc. 1986, 108, 4135. https://doi.org/10.1021/ja00274a047
  24. Echegoyen, L.; Gustowski, D. A.; Gatto, U. J.; Gokel, G. W. J.Chem. Soc. Chem. Commun. 1986, 220.
  25. Ozeki, E.; Kimnra, S.; Imanishi, Y. J. Chem. Soc, Chem. Commun.1988, 1353.
  26. Park, D. H.; Kang, S. O.; Lee, H.-J.; Nam, K. C.; Jeon, S. Bull.Korean Chem. Soc. 2001, 22, 638.

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