Ester hydrolysis by a cyclodextrin dimer catalyst with a tridentate N,N′,N″-zinc linking group

Chemistry - An Asian Journal

Volumn 4, Issue 8, 2009, Pages 1354-1360

  Tang, Si Ping ^a,b   Zhou, Ying Hua ^c   Chen, Huo Yan ^a   Zhao, Cun Yuan ^a   Mao, Zong Wan ^a   Ji, Liang Nian ^a  

^a SUN YAT SEN UNIVERSITY   (China)

^b HENGYANG NORMAL UNIVERSITY   (China)

^c ANHUI NORMAL UNIVERSITY   (China)

Author keywords

Cyclodextrins; Hydrolysis; Kinetics; Tridentate ligands; Zinc complex

Indexed keywords

AQUEOUS BUFFER; BIS(4-NITROPHENYL) PHOSPHATE; CATALYST CONCENTRATION; COORDINATED WATER; CYCLODEXTRIN DIMERS; DIESTERS; ESTER HYDROLYSIS; FIRST-ORDER RATE CONSTANTS; FORMATION CONSTANTS; HIGH RATE; HYDROLYSIS KINETICS; HYDROLYSIS RATE CONSTANTS; INFLECTION POINTS; LINKING GROUPS; NITROPHENYL PHOSPHATES; PH DEPENDENCE; PH TITRATION; PHENYL ACETATE; PHOSPHATE ESTERS; POTENTIOMETRIC TITRATIONS; PYRIDYL; RATE ENHANCEMENT; SIGMOIDAL CURVES; TRIDENTATE LIGANDS; UNCATALYZED HYDROLYSIS; ZINC COMPLEX;

CARBOXYLIC ACIDS; CATALYSIS; CATALYSTS; CYCLODEXTRINS; ESTERIFICATION; ESTERS; LIGANDS; ORGANIC ACIDS; POTENTIOMETERS (ELECTRIC MEASURING INSTRUMENTS); RATE CONSTANTS; SILANES; TITRATION; ZINC;

HYDROLYSIS;

BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; ESTER; ORGANOMETALLIC COMPOUND; ZINC;

ARTICLE; CATALYSIS; CHEMICAL PHENOMENA; CHEMISTRY; DIMERIZATION; HYDROLYSIS; KINETICS; SYNTHESIS;

BETA-CYCLODEXTRINS; CATALYSIS; DIMERIZATION; ESTERS; HYDROLYSIS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; KINETICS; ORGANOMETALLIC COMPOUNDS; ZINC;

EID: 68349144908     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200900108     Document Type: Article

References (41)

1. Y. Liu, Y. Chen, Acc. Chem. Res. 2006, 39, 681.
2. R. Breslow, N. Greenspoon, T. Guo, R. Zarzycki, J. Am. Chem. Soc. 1989, 111, 8296.
3. R. Bredow, S. Chung, J. Am. Chem. Soc. 1990, 112, 9659.
4. R. Bredow, S. Halfon, B. Zhang, Tetrahedron 1995, 51, 377.
5. R. C. Petter, C. T. Sikorski, D. H. Waldeck, J. Am. Chem. Soc. 1991, 113, 2325.
6. Y. Liu, C.-C. You, B. Li, Chem. Eur. J. 2001, 7, 1281.
7. R. Breslow, B. Zhang, J. Am. Chem. Soc. 1996, 118, 8495.
8. a) A. Ruebner, Z. W. Yang, D. Leung, R. Breslow, Proc. Natl. Acad. Sci. USA 1999, 96, 14692;
9. b) W. B. Edwards, D. E. Reichert, D. A. d'Avignon, M. J. Welch, Chem. Commun. 2001, 1312;
10. c) Y Liu, G.-S. Chen, Li, H.-Y Zhang, D.-X. Cao, Y.-J. Yuan, J. Med. Chem. 2003, 46, 4634.
11. S. D. P. Baugh, Z. Yang, D. K. Leung, D. M. Wilson, R. Breslow, J. Am. Chem. Soc. 2001, 123, 12488.
12. a) R. Breslow, S. D. Dong, Chem. Rev. 1998, 98, 1997;
13. b) R. Breslow, X. Zhang, R. Xu, M. Maletic, R. Merger, J. Am. Chem. Soc. 1996, 118, 11678.
14. a) R. Breslow, B. Zhang, J. Am. Chem. Soc. 1992, 114, 5882;
15. b) B. Zhang, R. Breslow, J. Am. Chem. Soc. 1997, 119, 1676;
16. c) R. Breslow, B. Zhang, J. Am. Chem. Soc. 1994, 116, 7893.
17. a) Z. Dong, X. Li, K. Liang, S. Mao , X. Huang, B. Yang, J. Xu, J. Liu, G. Luo, J. Shen, J. Org. Chem. 2007, 72, 606;
18. b) Z. Dong, J. Liu, S. Mao, X. Huang, B. Yang, X. Ren, G. Luo, J. Shen, J. Am. Chem. Soc. 2004, 126, 16395;
19. c) Z.-Y Dong, X. Huang, S.-Z. Mao, K. Liang, J.-Q. Liu, G.-M. Luo, J.-C. Shen, Chem. Eur. J. 2006, 12, 3575.
20. a) M. C. Feiters, A. E. Rowan, R. J. M. Nolte, Chem. Soc. Rev. 2000, 29, 375;
21. b) R. R. French, P. Holzer, M. G. Leuenberger, W.-D. Woggon, Angew. Chem. 2000, 112, 1321;
22. Angew. Chem. Int. Ed. 2000, 39, 1267.
23. H. Fu, Y.-H. Zhou, W.-L. Chen, Z.-G. Deqing, M.-L. Tong, L.-N. Ji, Z.-W Mao, J. Am. Chem. Soc. 2006, 128, 4924.
24. Y.-H. Zhou, H. Fu, W.-X. Zhao, W.-L. Chen, C.-Y Su, H. Sun, L.-N. Ji, Z.-W. Mao, Inorg. Chem. 2007, 46, 734.
25. Y.-H. Zhou, H. Fu, W.-X. Zhao, M.-L. Tong, C.-Y. Su, H. Sun, L.-N. Ji, Z.-W. Mao, Chem. Eur. J. 2007, 13, 2402.
26. Y.-H. Zhou, M. Zhao, J.-H. Li, Z.-W. Mao, L.-N. Ji, J. Mol. Catal. A 2008, 293, 59.
27. Y.-H. Zhou, M. Zhao, Z.-W. Mao, L.-N. Ji, Chem. Eur. J. 2008, 14, 7193.
28. X. Zhang, R. van Eldik, T. Koike, E. Kimura, Inorg. Chem. 1993, 32, 5749.
29. P. Molenveld, W M. G Stikvoort, H. Kooijman, A. L. Spek, J. F J. Engbersen, D. N Reinhoudt, J. Org. Chem. 1999, 64, 3896.
30. A. Nomura, Y Sugiura, Inorg. Chem. 2004, 43, 1708.
31. J. Chen, X. Wang, Y Zhu, J. Lin, X. Yang, Y Li, Y Lu, Z. Guo, Inorg. Chem. 2005, 44, 3422.
32. T. Koike, E. Kimura, J. Am. Chem. Soc. 1991, 113, 8935.
33. L. Bonfa, M. Gatos, F Mancin, P. Tecilla, U. Tonellato, Inorg. Chem. 2003, 42, 3943.
34. A. K. Yatsimirsky, Coord. Chem. Rev. 2005, 249, 1997.
35. T. Koike, E. Kimura, J. Am. Chem. Soc. 1991, 113, 8935.
36. P. Jurek, A. E. Martell, Inorg. Chim. Acta 1999, 287, 47.
37. F Ortega-Caballero, C. Rousseau, B. Christensen, T. E. Petersen, M. Bols, J. Am. Chem. Soc. 2005, 127, 3238.
38. F Ortega-Caballero, J. Bjerre, L. S. Laustsen, M. Bols, J. Org. Chem. 2005, 70, 7217.
39. L. Jicsinszky, R. Ivanyi, Carbohydr. Polym. 2001, 45, 139.
40. R. C. Petter, J. S. Salek, C. T. Sikorski, G. Kumaravel, F T. Lin, J. Am. Chem. Soc. 1990, 112, 3860.
41. G. Gran, Acta Chem. Scand. 1950, 4559.