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New polydentate macrocyclic ligands of hybrid amine-imine and amide-imine types as artificial anion receptors. Synthesis and study of anion binding

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Abstract

Three new macrocyclic Schiff bases containing an amine or amide structural fragment along with imine groups were synthesized by condensation of 2,6-bis(2-aminophenyliminomethyl)pyridine (1) and N, N’-bis(2-aminophenyl)pyridine-2,6-dicarboxamide (2) with 2,5-diformylpyrrole (3) and 2,2-bis(5-formylpyrrol-2-yl)propane (4). The reaction of compound 1 with 3 proceeds abnormally and is accompanied by redox disproportionation of compound 1 in the first step. The structure of the macrocyclic product of this reaction was established by X-ray diffraction analysis. Spectrophotometric titration showed that hybrid macrocycle 10, which was prepared by condensation of compound 2 with 4, possesses the properties of an anion receptor and selectively binds hydrosulfate and dihydrophosphate anions in the presence of bromide and nitrate anions. The structures of 10 and its adduct with the hydrosulfate anion were calculated by density functional theory.

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References

  1. J.-M. Lehn, Supramolecular Chemistry. Concept and Perspectives, VCH, Weinheim, 1995.

    Google Scholar 

  2. A. Bianchi, K. Bowman-James, and E. Garcia-Espaca, Supramolecular Chemistry of Anions, Wiley-VCH, New York, 1997.

    Google Scholar 

  3. P. D. Beer and P. A. Gale, Angew. Chem., Int. Ed. Engl., 2001, 40, 486.

    Google Scholar 

  4. R. Martinez-Macez and F. Sancenon, Chem. Rev., 2003, 103, 4419.

    Article  PubMed  Google Scholar 

  5. P. A. Gale, J. L. Sessler, V. Kral, and V. Lynch, J. Am. Chem. Soc., 1996, 118, 5140.

    Article  Google Scholar 

  6. J. L. Sessler, P. J. Anzenbacher, Jr., J. A. Shriver, K. Jursikova, V. M. Lynch, and M. Marquez, J. Am. Chem. Soc., 2000, 122, 12061.

    Article  Google Scholar 

  7. M. Van Kuijck, H. Miyaji, and J. L. Sessler, Supramolecular Chemistry, 2002, 13, 661.

    Google Scholar 

  8. W. Sato, H. Miyaji, and J. L. Sessler, Tetrahedron Lett., 2000, 41, 6731.

    Article  Google Scholar 

  9. A. Andrievsky, F. Ahuis, J. L. Sessler, F. Voegtle, D. Gudat, and M. Moini, J. Am. Chem. Soc., 1998, 120, 9712.

    Article  Google Scholar 

  10. J. L. Sessler, W.-S. Cho, S. P. Dudek, L. Hicks, V. M. Lynch, and M. T. Huggins, J. Porphyrins Phthalocyanines, 2003, 7, 97.

    Google Scholar 

  11. C.-H. Lee, H. K. Na, D.-W. Yoon, D.-H. Won, W.-S. Cho, V. M. Lynch, S. V. Shevchuk, and J. L. Sessler, J. Am. Chem. Soc., 2003, 125, 7301.

    Article  PubMed  Google Scholar 

  12. Yu. A. Ustynyuk, N. E. Borisova, V. M. Nosova, M. D. Reshetova, S. S. Talismanov, S. E. Nefedov, G. G. Aleksandrov, I. L. Eremenko, and I. I. Moiseev, Izv. Akad. Nauk, Ser. Khim., 2002, 454 [Russ. Chem. Bull., Int. Ed., 2002, 51, 488].

    Google Scholar 

  13. N. E. Borisova, Yu. A. Ustynyuk, M. D. Reshetova, G. G. Aleksandrov, I. L. Eremenko, and I. I. Moiseev, Mendeleev Commun., 2003, 2002.

  14. N. E. Borisova, M. D. Reshetova, and Yu. A. Ustynyuk, Izv. Akad. Nauk, Ser. Khim., 2004, 174 [Russ. Chem. Bull., Int. Ed., 2004, 53, 181].

    Google Scholar 

  15. E. A. Katayev, M. D. Reshetova, and Yu. A. Ustynyuk, Izv. Akad. Nauk, Ser. Khim., 2004, 322 [Russ. Chem. Bull., Int. Ed., 2004, 53, 335].

    Google Scholar 

  16. N. E. Borisova, Yu. A. Ustynyuk, M. D. Reshetova, G. G. Aleksandrov, I. L. Eremenko, and I. I. Moiseev, Izv. Akad. Nauk, Ser. Khim., 2004, 326 [Russ. Chem. Bull., 2004, Int. Ed., 53, 340].

    Google Scholar 

  17. J. L. Sessler, E. Katayev, G. D. Pantos, and Yu. A. Ustynyuk, Chem. Commun., 2004, 1276.

  18. C. Picard, N. Arnaud, and P. Tisnes, Synthesis, 2001, 1471.

  19. K. Kavallieratos, C. M. Bertao, and R. H. Crabtree, J. Org. Chem., 1999, 64, 1675.

    Article  PubMed  Google Scholar 

  20. K. Niikura, A. P. Bisson, and E. V. Anslyn, J. Chem. Soc., Perkin Trans. 2, 1999, 1111.

  21. J. B. Love, A. J. Blake, C. Wilson, S. D. Reid, A. Novak, and P. B. Hitchcock, Chem. Commun., 2003, 1682.

  22. K. Brychcy, K. Draeger, K.-J. Jens, M. Tilset, and U. Behrens, Chem. Ber., 1994, 127, 465.

    Google Scholar 

  23. F. Benetollo, G. Bombieri, K. K. Fonda, A. Polo, J. R. Quagliano, and L. M. Vallarino, Inorg. Chem., 1991, 30, 1345.

    Article  Google Scholar 

  24. G. J. Kirkovits, R. S. Zimmerman, M. T. Huggins, V. M. Lynch, and J. L. Sessler, Eur. J. Org. Chem., 2002, 3768.

  25. J. L. Sessler, G. D. Pantos, E. Katayev, and V. M. Lynch, Org. Lett., 2003, 5, 4141.

    Article  PubMed  Google Scholar 

  26. K. A. Connors, Binding Constants; John Wiley & Sons, New York, 1987, (a) p. 148; (b) p. 24.

    Google Scholar 

  27. P. D. Beer, D. Hesek, and K. C. Nam, Organometallics, 1999, 18, 3933.

    Article  Google Scholar 

  28. K. Choi and A. D. Hamilton, J. Am. Chem. Soc., 2001, 123, 2456.

    Article  PubMed  Google Scholar 

  29. S. Kubik, R. Kirchner, D. Nolting, and J. Seidel, J. Am. Chem. Soc., 2002, 124, 12752.

    Article  PubMed  Google Scholar 

  30. H. Ihm, S. Yun, H. G. Kim, J. K. Kim, and K. S. Kim, Org. Lett., 2002, 4, 2897.

    Article  PubMed  Google Scholar 

  31. R. Herges, A. Dikmans, U. Jana, F. Kohler, P. G. Jones, I. Dix, T. Fricke, and B. Konig, Eur. J. Org. Chem., 2002, 3004.

  32. D. H. Lee, H. Y. Lee, and J.-I. Hong, Tetrahedron Lett., 2002, 43, 7273.

    Article  Google Scholar 

  33. S. O. Kang, J. M. Oh, Y. S. Yang, J. C. Chun, S. Jeon, and K. C. Nam, Bull. Korean Chem. Soc., 2002, 23, 145.

    Google Scholar 

  34. S. J. Coles, G. Denuault, P. A. Gale, P. N. Horton, M. B. Hursthouse, M. E. Light, and C. N. Warriner, Polyhedron, 2003, 22, 699.

    Article  Google Scholar 

  35. S. O. Kang, J. M. Llinares, D. Powell, D. Vander Velde, and K. Bowman-James, J. Am. Chem. Soc., 2003, 125, 10152.

    Article  PubMed  Google Scholar 

  36. S. L. Tobey and E. V. Anslyn, J. Am. Chem. Soc., 2003, 125, 14807.

    Article  PubMed  Google Scholar 

  37. Y. S. Yang, S. W. Ko, I. H. Song, B. J. Ryu, and K. C. Nam, Bull. Korean Chem. Soc., 2003, 24, 681.

    Google Scholar 

  38. J. D. Vienna, M. J. Schweiger, D. E. Smith, H. D. Smith, J. V. Crum, D. K. Peeler, I. A. Reamer, C. A. Musick, and R. D. Tillotson, Report PNNL-12234, Pacific Northwest National Laboratory, Richland, Washington, July 1999.

  39. C. I. Crawford, D. M. Ferrara, R. F. Schumacher, and N. E. Bibler, Report WSRC-MS-2002-00449, Westinghouse Savannah River Company, Aiken, South Carolina, Apr. 2002.

  40. D. E. Kurath, J. R. Bontha, D. L. Blanchard, S. K. Fiskum, and B. M. Rapko, Report PNWD-3053, BNFL-RPT-036, Rev. 0, Pacific Northwest National Laboratory, Richland, Washington, USA, August 2000.

  41. B. A. Moyer, L. H. Delmau, C. J. Fowler, A. Ruas, D. A. Bostick, J. L. Sessler, J. M. Llinares, A. Hossain, S. O. Kang, and K. Bowman-James, Supramolecular Chemistry of Environmentally Relevant Anions, ACS Symp. Ser., American Chemical Society, Washington, D. C., 2005–2006.

    Google Scholar 

  42. M. Freemantle, Chem. Eng. News, 2004, 82, No.23, 8.

    Google Scholar 

  43. R. Miller and K. Olsson, Acta Chem. Scand. Ser. B, 1981, 35, 303.

    Google Scholar 

  44. Z. Otwinowski and W. Minor, in Methods in Enzymology, 276: Macromolecular Crystallography, Part A, Eds C. W. Carter, Jr., and R. M. Sweets, Academic Press, New York, 1997, p. 307.

    Google Scholar 

  45. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, and R. J. Spagna, J. Appl. Cryst., 1999, 32, 115.

    Article  Google Scholar 

  46. G. M. Sheldrick, SHELXL97. Program for the Refinement of Crystal Structures, University of Gottingen, Gottingen Germany, 1994.

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119992, Moscow, Russian Federation

    E. A. Katayev, M. D. Reshetova & Yu. A. Ustynyuk

  2. Department of Chemistry and Biochemistry and Institute for Cellular and Molecular Biology, University of Texas at Austin, 1 University Station, A5300, Austin, Texas, 78712 0165, USA

    G. D. Pantos, V. M. Lynch & J. L. Sessler

Authors
  1. E. A. Katayev
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  2. G. D. Pantos
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  3. V. M. Lynch
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  4. J. L. Sessler
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  5. M. D. Reshetova
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  6. Yu. A. Ustynyuk
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 161–168, January, 2005.

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Katayev, E.A., Pantos, G.D., Lynch, V.M. et al. New polydentate macrocyclic ligands of hybrid amine-imine and amide-imine types as artificial anion receptors. Synthesis and study of anion binding. Russ Chem Bull 54, 165–172 (2005). https://doi.org/10.1007/s11172-005-0233-4

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  • DOI: https://doi.org/10.1007/s11172-005-0233-4

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