Advertisement

Investigation of Host–Guest Compounds of Cucurbit[n=5–8]uril with Some Ortho Aminopyridines and Bispyridine

  • Hai-Yan Fu
  • Sai-Feng Xue
  • Qian-Jiang Zhu
  • Zhu Tao
  • Jian-Xin Zhang
  • Anthony I. Day
Article

Abstract

Host–guest complexes of cucurbit[n=5–8]uril and some examples of ortho substituted pyridines or aminopyridines were examined by 1H NMR spectroscopy. Portal binding of two ortho aminopyridine free bases, by cucurbit[5]uril, was observed in 1H NMR spectra. Combined cavity and portal binding in cucurbit[6]uril were observed for both the free base 2-aminomethylpyridine, ampy, the HCl salt, ampy·1HCl, and the salt of 2,2′-bispyridine, bpy·1HCl. Two novel complexes were formed with cucurbit[6]uril. The free base ampyas a dual occupant, formed a 2:1 complex, and bpy·1HCl formed a stable asymmetric 1:1 complex. Only portal binding of 2,6-bisaminomethylpyridine and its salts was observed for cucurbit[6]uril. Fast exchange of the free base and pyridineammonium salts was observed for cucurbit[7-8]uril.

Keywords

cavity binding cucurbit[5]uril cucurbit[6]uril host–guest portal binding pyridine binding 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    (a) W.A. Freeman, W.L. Mock, and N.Y. Shih: J. Am. Chem. Soc. 103 , 7367 (1981); (b) J. Kim, I.-S. Jung, S.-Y. Kim, E. Lee, J.-K. Kang, S. Sakamoto, K. Yamaguchi, and K. Kim: J. Am. Chem. Soc. 122, 540 (2000); (c) A. Day, A.P. Arnold, R.J. Blanch, and B. Snushall: J. Org. Chem. 66 , 8094 (2001); (d) K. Jansen, H.-J. Buschmann, A. Wego, D. Dopp, C. Mayer, H.-J. Drexler, H.-J. Holdt, and E. Schollmeyer: J. Incl. Phenom. Macrocycl. Chem. 39 , 357 (2001)Google Scholar
  2. 2.
    Marquez, C., Nau, W.N. 2001Angew Chem Int Ed Engl.403155Google Scholar
  3. 3.
    Day, A.I., Blanch, R.J., Arnold, A.P., Lorenzo, S., Lewis, G.R., Dance, I. 2002Angew Chem Int Ed Engl.41275PubMedGoogle Scholar
  4. 4.
    Reviews: (a) J.W. Lee, S. Samal, N. Selvapalam, H.-J. Kim, and K. Kim: Accounts Chem. Res . ASAP (2003); (b) O.A. Gerasko, D.G. Samsonenko, and V.P. Fedin: Rus. Chem. Rev. 71 , 741 (2002); (c) T.J. Hubin, A.G. Kolchinski, A.L. Vance, and D.H. Busch: Adv. Supramol. Chem. 5 , 237 (1999); (d) W.L. Mock: Top. Curr. Chem . 175 , 1 (1995); (e) P. Cintas: J. Incl. Phenom. Mol. Recogn. Chem . 17 , 205 (1994); (f) J.A.A.W. Elemans, A.E. Rowan, and R.J.M. Nolte: Ind. Eng. Chem. Res. 39 , 3419 (2000); (g) C. Marquez, R. R.Hudgins, and W.M. Nau: J. Am. Chem. Soc. 126 , 5806 (2004)Google Scholar
  5. 5.
    Blanch, R.J., Sleeman, A.J., White, T.J., Arnold, A.P., Day, A.I. 2002Nano Lett.2147Google Scholar
  6. 6.
    (a) J. Heo, J. Kim, D. Whang, and K. Kim: Inorg. Chim. Acta 297 , 307 (2000); (b) J. Heo, S.-Y. Kim, D. Whang, and K. Kim: Angew. Chem. Int. Ed. Engl. 38 , 641 (1999); (c) D. Whang, J. Heo, J.H. Park, and K. Kim: Angew. Chem. Int. Ed. Engl. 37 , 78 (1998); (d) Y.-M Jeon, J. Kim, D. Whang, and K. Kim: J. Am. Chem. Soc. 118 , 9790 (1996)Google Scholar
  7. 7.
    (a) H.-J. Buschmann, K. Jansen, C. Meschke, and E. Schollmeyer: J. Solution Chem . 27 , 135 (1998); (b) H.-J. Buschmann and E. Schollmeyer: Inorg. Chim. Acta 193 , 93 (1992); (c) R. Hoffmann, W. Knoche, C. Fenn, and H.-J. Buschmann: J. Chem. Soc. Faraday Trans. 90 , 1507 (1994); (d) H.-J. Buschmann, E. Cleve, K. Jansen, A. Wego, and E. Schollmeyer: J. Incl. Phenom. Macrocycl. Chem. 40 , 117 (2001)Google Scholar
  8. 8.
    Zhang, X.X., Krakowiak, K.E., Xue, G., Bradshaw, J.S., Izatt, R.M. 2000Ind Eng Chem Res.393516Google Scholar
  9. 9.
    (a) D. Whang, J. Heo, C.-A. Kim, and K. Kim: Chem. Commun. 2361 (1997); (b) H.-J. Buschmann, C. Meschke, and E. Schollmeyer: Anal. Quim. Int. Ed. 94 , 241 (1998); (c) J.W. Lee, S.W. Choi, Y.H. Ko, S.-Y. Kim, and K. Kim: Bull. Kor. Chem. Soc. 23 , 1347 (2002)Google Scholar
  10. 10.
    McBryde, W.A.E. 1965Can J Chem.433472Google Scholar
  11. 11.
    Matsumoto I., Kubo K. (1974). Appl. JP 70-8643819701003Google Scholar
  12. 12.
    Day, A.I., Blanch, R.J., Coe, A., Arnold, A.P. 2002J Incl Phenom Macrocycl Chem.43247Google Scholar
  13. 13.
    Tuncel D., Steinke H.G. (2002). Chem Commun. 496Google Scholar

Copyright information

© Springer 2005

Authors and Affiliations

  • Hai-Yan Fu
    • 1
  • Sai-Feng Xue
    • 1
  • Qian-Jiang Zhu
    • 1
  • Zhu Tao
    • 1
  • Jian-Xin Zhang
    • 2
  • Anthony I. Day
    • 3
  1. 1.Institute of Applied ChemistryGuizhou UniversityGuiyangPeoples Republic of China
  2. 2.The Key Laboratory of Chemistry for Natural Products of Guizhou ProvinceGuiyangPeoples Republic of China
  3. 3.Discipline of Chemistry, School of Physical, Environmental and Mathematical Sciences, University College (UNSW)Australian Defence Force AcademyCanberraAustralia

Personalised recommendations