Molecular receptors for adenine and guanine employing metal coordination, hydrogen-bonding and π-stacking interactions

Chemistry - A European Journal

Volumn 3, Issue 8, 1997, Pages 1203-1213

  Kickham, James E ^a   Loeb, Stephen J ^a   Murphy, Shannon L ^a  

^a UNIVERSITY OF WINDSOR   (Canada)

Author keywords

Hydrogen bonds; Metalloreceptor; Molecular recognition; Nucleobases; pi interactions

Indexed keywords

EID: 0030758851     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030807     Document Type: Article

References (38)

1. a) J. F. Stoddart, H. M. Colquhoun, Angew. Chem. Int. Ed. Engl. 1986, 25, 487;
2. b) J. F. Stoddart, R. Zarzycki, in Cation Binding by Macrocycles (Ed.: G. W. Gokel, Y. Inoue), Marcel Dekker, New York, 1990, pp. 631;
3. c) S. J. Loeb, in Comprehensive Supramolecular Chemistry, Vol. 1 (Ed.: G. W. Gokel), Pergamon, Oxford, 1996, Chapt. 20, pp. 733.
4. a) J. E. Kickham, S. J. Loeb, J. Chem. Soc. Chem. Commun. 1993, 1848;
5. b) J. E. Kickham, S. J. Loeb, Inorg. Chem. 1994, 33, 4351;
6. c) J. E. Kickham, S. J. Loeb, ibid. 1995, 34, 5656.
7. d) J. E. Kickham, S. J. Loeb, Organometallics 1995, 14, 3584.
8. J. E. Kickham, S. J. Loeb, S. L. Murphy, J. Am. Chem. Soc. 1993, 115, 7031;
9. a) M. Shionoya, E. Kimura, M. Shiro, J. Am. Chem. Soc. 1993, 115, 6730;
10. b) M. Shionoya, T. Ikeda, E. Kimura, M. Shiro, ibid. 1994, 116, 3848.
11. a) C. J. van Staveren, J. van Eerden, F. C. J. M. van Veggel, S. Harkema, D. N. Reinhoudt, J. Am. Chem. Soc. 1988, 110, 4994;
12. b) M. T. Reetz, C. M. Niemeyer M. Hermes, M. Goddard, Angew. Chem. Int. Ed. Engl. 1992, 31, 135;
13. c) A. R. van Doorn, D. J. Rushton, W. F. van Staveren-Nijenhuis, W. Verboom, D. N. Reinhoudt, Reel. Trav. Chim. Pays-Bas, 1992, 111, 421.
14. Y. Aoyama, A. Yamagishi, M. Asagawa, H. Toi, H. Ogoshi, J. Am. Chem. Soc. 1988, 110, 4076;
15. b) T. Mizutani, T. Ema, T. Yoshida, Y. Kurado, H. Ogoshi, Inorg. Chem. 1993, 32, 2072.
16. c) H. Chen, S. Ogo, R. H. Fish, J. Am. Chem. Soc. 1996, 118, 4993 and references therein.
17. a) S. C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196 and references therein;
18. b) T. Tjama, G. Deslongchamps, J. Rebek Jr., ibid. 1990, 112, 8408;
19. c) K. S. Jeong, T. Tjivikua, A. Muehldorf, G. Deslongchamps, J. Rebek Jr., ibid. 1991, 113, 201;
20. d) G. Deslongchamps, A. Galan, J. de Mendoza, J. Rebek Jr.. Angew. Chem. Int. Ed. Engl. 1992, 31, 61 and references therein;
21. e) C. E. Osterberg, C. E. A. M. Arif, T. G. Richmond, J. Am. Chem. Soc 1988, 110, 6903;
22. f) D. P. Smith, E. Baralt, E. B. Morales, M. M. Olmstead, M. F. Maestre, R. H. Fish, ibid. 1992, 114, 10647 and references therein;
23. g) Z. W. Li, H. Taube, Science, 1992, 256, 210.
24. D. Voet, J. G. Voet, Biochemistry, 2nd ed., Wiley, New York, 1995, p. 868.
25. a) J. Buter, R. M. Kellogg, J. Org. Chem. 1981, 4481;
26. b) J. Buter, R. M. Kellogg, Org. Synth. 1987, 65, 150.
27. a) G. S. Hanan, J. E. Kickham, S. J. Loeb, Organometallics, 1992, 11, 3063;
28. b) G. R. Giesbrecht, G. S. Hanan, J. E. Kickham, S. J. Loeb, Inorg. Chem. 1992, 31, 3286.
29. CRC Handbook of Nucleobase Complexes: Transition Metal Complexes of Naturally Occurring Nucleabases and Their Derivatives, Vol. I (Ed.: J. R. Lusty), CRC Press, Boca Raton, FL, 1990, pp. 9-99.
30. C. Price, M. R. J. Elsegood, W. Clegg, A. Houlton, J. Chem. Soc. Chem. Commun. 1995, 2165.
31. a) G. R. Desiraju, In Crystal Engineering: The Design of Organic Solids, Materials Science Monographs: No. 54, Elsevier, 1989, p 92;
32. b) C. A. Hunter, J. K. Sanders, J. Am. Chem. Soc. 1990, 112, 5525;
33. c) S. K. Burley, G. A. Petsko, ibid. 1986, 108, 7995.
34. TEXSAN-TEXRAY Structure Analysis Package, Molecular Structure Corp. (1985).
35. D. T. Cromer, J. T. Waber, International Tables for X-ray Crystallography, Kynoch Press, Birmingham, 1974, Vol. IV, Table 2.2A.
36. a) J. A. Ibers, H. A. Hamilton, Acta Crystallogr. 1974, 17, 781;
37. b) D. T. Cromer, International Tables for X-ray Crystallography, Kynoch Press, Birmingham, 1974, Vol. IV, Table 2.3.1.
38. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100 176. Copies of the data can be obtained free of charge on application to the The Director, CCDC, 12 Union Road, Cambridge, CB21EZ, UK (Fax: Int. code +(1223)336-033; e-mail: teched@chemcrys.cam.ac.uk).