Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A Novel Linking Schiff-Base Type Ligand (L: py-CH=N-C6H4-N=CH-py) and Its Zinc Coordination Polymers:Preparation of L, 2-Pyridin-3-yl-1H-benzoimidazol, trans-[Zn(H2O)4L2].(NO3)2.(MeOH)2[Zn(NO3)(H2O)2(L)].(NO3).(H2O)2 and [Zn(L)(OBC)(H2O)] (OBC = 4,4'-Oxybis(benzoate))

  • Kim, Han-Na (Department of Chemistry (BK21), Institute of Basic Science, Sungkyunkwan University, Natural Science Campus) ;
  • Lee, Hee-K. (Department of Chemistry (BK21), Institute of Basic Science, Sungkyunkwan University, Natural Science Campus) ;
  • Lee, Soon-W. (Department of Chemistry (BK21), Institute of Basic Science, Sungkyunkwan University, Natural Science Campus)
  • Published : 2005.06.20
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Abstract

A long, bis(monodentate), linking Schiff-base ligand L (py-CH=N-$C_6H_4$-N=CH-py) was prepared from 1,4-phenylenediamine and 3-pyridinecarboxaldehyde by the Schiff-base condensation. Ligand L has two terminal pyridyl groups capable of coordinating to metals through their nitrogen atoms. In contrast, the same reaction between 1,2-phenylenediamine and 3-pyridinecarboxaldehyde produced a mixture of imidazol isomers (2-pyridin-3-yl-1H-benzoimidazole), which are connected to one another by the N-H…N hydrogen bonding to form a tetramer. From Zn($NO_3)_2{\cdot}6H_2O$ and ligand L under various conditions, one discrete molecule, trans- [Zn($H_2O)_4L_2]{\cdot}(NO_3)_2{\cdot}(MeOH)_2$, and two 1-D zinc polymers, [Zn$(NO_3)(H_2O)_2(L)]{\cdot}(NO_3){\cdot}(H_2O)_2$ and [Zn(L) (OBC)($H_2O$)], were prepared. In ligand L, the N$\ldots$N separation between the terminal pyridyl groups is 13.994 $\AA$, with their nitrogen atoms at the meta positions (3,3’) in a trans manner. The corresponding N$\ldots$N separations in its compounds range from 13.853 to 14.754 $\AA$.

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References

  1. Janiak, C. Dalton Trans. 2003, 2781
  2. Kesanli, B.; Lin, W. Coord. Chem. Rev. 2003, 246, 305 https://doi.org/10.1016/j.cct.2003.08.004
  3. Swiergers, G. F.; Malefetse, T. J. Coord. Chem. Rev. 2002, 225, 91 https://doi.org/10.1016/S0010-8545(01)00407-6
  4. Eddaoudi, M.; Kim, J.; Rosi, N.; Vodak, D.; Wachter, J.; O'Keeffe, M.; Yaghi, O. M. Science 2002, 295, 469 https://doi.org/10.1126/science.1067208
  5. Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629 https://doi.org/10.1021/cr9900432
  6. Swiergers, G. F.; Malefetse, T. J. Chem. Rev. 2000, 100, 3 https://doi.org/10.1021/cr990110s
  7. Calligaris, M.; Randaccio, L. Schiff Bases as Acyclic Polydentate Ligands in Comprehensive Coordination Chemistry; Wilikinson, G.; Gillard, R. D.; McCleverty, J. A., Eds.; Pergamon Press: New York, 1987; Vol. 2, pp 715-738
  8. Vigato, P. A.; Tanburini, S. Coord. Chem. Rev. 2004, 248, 1717 and references therein https://doi.org/10.1016/j.cct.2003.09.003
  9. Hernanddez-Molina, R.; Mederos, A. Acyclic and Macrocyclic Schiff Base Ligands in Comprehensive Coordination Chemistry II; McCleverty, J. A.; Meyer, T. J., Eds.; Pergamon Press: New York, 2004; Vol. 2, pp 411-446
  10. Yaghi, O. M.; Li, H.; Davis, C.; Richardson, D.; Groy, T. L. Acc. Chem. Res. 1998, 31, 474 https://doi.org/10.1021/ar970151f
  11. Batten, S. R.; Robson, R. Angew. Chem., Int. Ed. 1998, 37, 1460 https://doi.org/10.1002/(SICI)1521-3773(19980619)37:11<1460::AID-ANIE1460>3.0.CO;2-Z
  12. Batten, S. R.; Champness, N. R. Coord. Chem. Rev. 2003, 246, 145 https://doi.org/10.1016/S0010-8545(03)00121-8
  13. Zaman, M. B.; Tomura, M.; Yamashita, Y. Org. Lett. 2000, 2, 273 https://doi.org/10.1021/ol991229q
  14. Lopez, S.; Kahraman, M.; Harmata, M.; Keller, S. W. Inorg. Chem. 1997, 36, 6138 https://doi.org/10.1021/ic970703q
  15. LaDuca Jr., R. L.; Desciak, M.; Laskoski, M.; Rarig Jr., R. S.; Zubieta, J. J. Chem. Soc. Dalton Trans. 2000, 2255
  16. Rarig Jr., R. S.; Zubieta, J. Polyhedron 2003, 22, 177 https://doi.org/10.1016/S0277-5387(02)01268-8
  17. Zaman, M. B.; Smith, M. D.; Ciurtin, D. M.; zur Loye, H.-C. Inorg. Chem. 2002, 41, 4895 https://doi.org/10.1021/ic011305x
  18. Bosch, E.; Barnes, C. L. New J. Chem. 2001, 25, 1376 https://doi.org/10.1039/b106221m
  19. Withersby, M. A.; Blake, A. L.; Champness, N. R.; Cooke, P. A.; Hubberstey, P.; Li, W.-S.; Schroder, M. Inorg. Chem. 1999, 38, 2259 https://doi.org/10.1021/ic980898h
  20. Dong, Y.-B.; Smith, M. D.; Layland, R. C.; zur Loye, H.-C. Chem. Mater. 2000, 12, 1156 https://doi.org/10.1021/cm9907965
  21. Dong, Y.-B.; Smith, M. D.; zur Loye, H.-C. Inorg. Chem. 2000, 39, 4927 and references therein https://doi.org/10.1021/ic0006504
  22. Dong, Y.-B.; Smith, M. D.; zur Loye, H.-C. J. Solid State Chem. 2000, 155, 143 https://doi.org/10.1006/jssc.2000.8915
  23. Constable, E. C.; Morris, D.; Carr, S. New J. Chem. 1998, 287
  24. Min, D.; Yoon, S. S.; Lee, J. H.; Suh, M.; Lee, S. W. Inorg. Chem. Commun. 2001, 4, 297 https://doi.org/10.1016/S1387-7003(01)00197-6
  25. Min, D.; Yoon, S. S.; Jung, D. Y.; Lee, C. Y.; Kim, Y.; Han, W. S.; Lee, S. W. Inorg. Chim. Acta 2001, 324, 293 https://doi.org/10.1016/S0020-1693(01)00621-1
  26. Huh, H. S.; Min, D.; Lee, Y. K.; Lee, S. W. Bull. Korean Chem. Soc. 2002, 23, 619 https://doi.org/10.5012/bkcs.2002.23.4.619
  27. Min, D.; Yoon, S. S.; Lee, S. W. Inorg. Chem. Commun. 2002, 5, 143 https://doi.org/10.1016/S1387-7003(01)00366-5
  28. Lee, S. W.; Kim, H. J.; Lee, Y. K.; Park, K.; Son, J.-H.; Kwon, Y.-U. Inorg. Chim. Acta 2003, 353, 151 https://doi.org/10.1016/S0020-1693(03)00246-9
  29. Choi, E.-Y.; Park, K.; Yang, C.-M.; Kim, H.; Son, J.-H.; Lee, S. W.; Lee, Y. H.; Min, D.; Kwon, Y.-U. Chem. Eur. J. 2004, 10, 5535 https://doi.org/10.1002/chem.200400178
  30. Lee, H. K.; Min, D.; Cho, B.-Y.; Lee, S. W. Bull. Korean Chem. Soc. 2004, 25, 619
  31. Cho. B.-Y.; Min, D.; Lee, S. W. Polyhedron submitted
  32. Bruker, SHELXTL, Structure Determination Software Programs; Bruker Analytical X-ray Instruments Inc.: Madison, Wisconsin, USA, 1997
  33. Holman, K. T.; Hammud, H. H.; Isber, S.; Tabbal, M. Polyhedron 2005, 24, 221 https://doi.org/10.1016/j.poly.2004.11.017

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