Anion recognition by a novel Fipronil-based receptor: efficient deprotonation or stable intermolecular hydrogen bonding

Tetrahedron Letters

Volumn 49, Issue 6, 2008, Pages 1087-1090

  Liu, Chuanxiang ^a   Qian, Xuhong ^a   Wang, Jiaobing ^a   Li, Zhong ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FIPRONIL;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT;

EID: 37849035903     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.155     Document Type: Article

References (44)

1. Bianchi A., Bowman-James K., and García-España E. Supramolecular Chemistry of Anions (1997), Wiley-VCH, New York pp 63-78
2. For reviews, see:. Beer P.D. Acc. Chem. Res. 31 (1998) 71
3. Beer P.D., and Gale P.A. Angew. Chem. 113 (2001) 502
4. Angew. Chem., Int. Ed. 40 (2001) 486
5. Bondy C.R., and Loeb S.J. Coord. Chem. Rev. 240 (2003) 77
6. Choi K., and Hamilton A.D. Coord. Chem. Rev. 240 (2003) 101
7. Gale P.A. Coord. Chem. Rev. 240 (2003) 191
8. Gale P.A., and Quesada R. Coord. Chem. Rev. 250 (2006) 3219
9. Suksai C., and Tuntulani T. Chem. Soc. Rev. 32 (2003) 192
10. Bowman-James C. Acc. Chem. Res. 38 (2005) 671
11. Gunnlaugsson T., Glynn M., Tocci G.M., Kruger P.E., and Pfeffer F.M. Coord. Chem. Rev. 250 (2006) 3094
12. Amendola V., Esteban Gómez D., Fabbrizzi L., and Licchelli M. Acc. Chem. Res. 39 (2006) 343
13. Yoon J., Kim S.K., Singh N.J., and Kim K.S. Chem. Soc. Rev. 35 (2006) 355
14. Snowden T.S., and Anslyn E.V. Chem. Biol. 3 (1999) 740
15. Schmidtchen F.P., and Berger M. Chem. Rev. 97 (1997) 1609
16. Steiner T. Angew. Chem., Int. Ed. 41 (2002) 48
17. Boiocchi M., Del Boca L., Esteban Gómez D., Fabbrizzi L., Licchelli M., and Monzani E. J. Am. Chem. Soc. 126 (2004) 16507
18. Gunnlaugsson T., Kruger P.E., Jensen P., Tiemey J., Ali H.D.P., and Hussey G.M. J. Org. Chem. 70 (2005) 10875
19. Gunnlaugsson T., Davis A.P., O'Brien J.E., and Glynn M. Org. Lett. 4 (2002) 2449
20. Kondo S.-i., Suzuki T., and Yano Y. Tetrahedron Lett. 43 (2002) 7059
21. Inoue Y., Kanbara T., and Yamamoto T. Tetrahedron Lett. 44 (2003) 5167
22. Gale P.A. Chem. Commun. (2005) 3761
23. Causey C.P., and Allen W.E. J. Org. Chem. 67 (2002) 5963
24. Sessler J.L., Pantos G.D., Katayev E., and Lynch V.M. Org. Lett. 5 (2003) 4141
25. Wu F.-Y., Li Z., Wen Z.-C., Zhou N., Zhao Y.-F., and Jiang Y.-B. Org. Lett. 4 (2002) 3203
26. Peng X., Wu Y., Fan J., Tian M., and Han K. J. Org. Chem. 70 (2005) 10524
27. Wu Y., Peng X., Fan J., Gao S., Tian M., Zhao J., and Sun S. J. Org. Chem. 72 (2007) 62
28. Wu J.S., Zhou J.H., Wang P.F., Zhang X.H., and Wu S.K. Org. Lett. 7 (2005) 2133
29. Kim Y.K., Lee Y.-H., Lee H.-Y., Kim M.-K., Cha G.S., and Ahn K.H. Org. Lett. 5 (2003) 4003
30. Esteban Gómez D., Fabbrizzi L., Licchelli M., and Monzani E. Org. Biomol. Chem. 3 (2005) 1495
31. This case can see as chemdosimeter approach for anion detection, for review see:. Martínez-Máñez R., and Sancenón F. Chem. Rev. 103 (2003) 4419
32. Martínez-Máñez R., and Sancenón F.. Coord. Chem. Rev. 250 (2006) 3081
33. Tomlin, C. D. S., Ed.; The Pesticide Manual, 12th ed.; British Crop Protection Council: Farnham, UK, 2000; pp 413-415.
34. Goller R., Vors J.P., Caminade A.M., and Majoral J.P. Tetrahedron Lett. 42 (2001) 3587
35. 2: 461.9521. Found: 461.9544.
36. 2: 477.9488. Found: 477.9493.
37. Connors A.K. Binding Constants: The Measurement of Molecular Complex Stability (1987), Wiley-VCH, New York
38. Colliot, F.; Kukorowski, K. A.; Hawkins, D. W.; Roberts, D. A. British Crop Protection Council: Farnham, UK, 1992, Vol. 1, p 29.
39. Dryden M.W., Denenberg T.M., and Bunch S. Vet. Parasitol. 93 (2000) 69
40. Cole L.M., Nicholson R.A., and Casida J.E. Pestic. Biochem. Physiol. 46 (1993) 47
41. Hainzl D., and Casida J.E. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 12764
42. Hainzl D., Cole L.M., and Casida J.E. Chem. Res. Toxicol. 11 (1998) 1529
43. Bobe' A., Meallier P., Cooper J.-F., and Coste C.M. J. Agric. Food Chem. 46 (1998) 2834
44. Caboni P.L., Sammelson R.E., and Casida J.E. J. Agric. Food Chem. 51 (2003) 7055