Servicios Personalizados
Articulo
Indicadores
Links relacionados
- Citado por Google
- Similares en Google
Compartir
South African Journal of Chemistry
versión On-line ISSN 1996-840X
versión impresa ISSN 0379-4350
S.Afr.j.chem. (Online) vol.63 Durban 2010
RESEARCH ARTICLE
Imidazole-based vanadium complexes as haloperoxidase models for oxidation reactions
Ryan S. Walmsley*; Zenixole R. Tshentu
Department of Chemistry, Rhodes University, Grahamstown 6140, South Africa
ABSTRACT
Four imidazole-bound oxovanadium(IV) haloperoxidase model complexes were prepared. Two heterogeneous catalysts were prepared by first linking imidazole-4-carboxylic acid or 1-methylimidazole-2-carboxylic acid to chloromethylated polystyrene and subsequently reacting these polymer-anchored ligands with vanadyl sulphate. Two homogeneous catalysts were prepared by reaction vanadyl sulphate with the free ligands. The activity of the catalysts was evaluated for the hydrogen peroxide facilitated oxidation of styrene and ethylbenzene and thioanisole. A maximum conversion of 99.9 % for styrene and 10.6 % for ethylbenzene was achieved. Excellent conversions of thioanisole (100 %) were obtained under mild room temperature conditions. The heterogeneous catalysts also proved to be recyclable for this reaction, with no appreciable loss in activity even after three catalytic cycles. The haloperoxidase activity was evaluated spectrophotometrically by following the bromination of phenol red to bromophenol blue. All four catalysts proved effective in catalysing this process.
Keywords: Oxovanadium, imidazole, catalysis, oxidation
Full text available only in PDF format.
Acknowledgements
The authors would like to thank the DST/Mintek National Innovation Centre (Rhodes University) for microanalysis data as well as the Electron Microscopy Unit (Rhodes University) for SEM images. We also thank Sasol and NRF for financial support.
References
1 D. Rehder, Bioorganic Vanadium Chemistry, John Wiley and Sons, West Sussex, 2008. [ Links ]
2 M.J. Clague, N.L. Keder, A. Butler, Inorg. Chem., 1993, 32, 4754-4761. [ Links ]
3 M. Weyand, H.J. Hecht, M. Kieß, M.F. Liaud, H. Vilter, D. Schomburg J. Mol. Biol., 1999, 293, 595-611. [ Links ]
4 M. Mba, M. Pontini, S. Lovat, C. Zonta, G. Bernardinelli, P.E. Kündig, G. Licini, Inorg. Chem., 2008, 47, 8616-8618. [ Links ]
5 M.R. Maurya, A. Arya, A. Kumar, J.C. Pessoa, Dalton Trans., 2009, 2185-2195. [ Links ]
6 M.R.Maurya,M.Kumar,A.Arya, Catal. Commun., 2008, 10,187-191. [ Links ]
7 M.R. Maurya, A. Kumar, M. Ebel, D. Rehder, Inorg. Chem, 2006, 45, 5924-5937. [ Links ]
8 M.R. Maurya, A. Arya, P. Adao, J.C. Pessoa, Appl. Catal, A, 2008, 351, 239-252. [ Links ]
9 C.J. Schneider, J.E. Penner-Hahn, V.L. Pecoraro, J. Am. Chem. Soc, 2008, 130, 2712-2713. [ Links ]
10 Z.R. Tshentu, C. Togo, R.S. Walmsley, J. Mol. Cat. A: Chem., 2010, 318, 30-35. [ Links ]
11 M.R. Maurya, A.K. Chandrakar, S. Chand, J. Mol. Cat. A: Chem., 2007, 274, 192-201. [ Links ]
12 R. Ando, T. Yagyu, M. Maeda, Inorg. Chim. Acta, 2004, 357, 2237-2244. [ Links ]
13 J.S. Reichert, S.A. McNeight, H.W. Rudel, Ind. Eng. Chem., 1939, 11, 194-197. [ Links ]
14 K.J. Oberhausen, J.F. Richardson, R.M. Buchanan, W. Pierce, Polyhedron, 1989, 8, 659-668. [ Links ]
15 C.C. McLauchlan, J.D. Hooker, M.A. Jones, Z. Dymon, E.A. Backhus, B.A. Greiner, N.A. Dorner, M.A. Youkhana, L.M. Manus, J. Inorg. Biochem, 2010, 104, 274-281. [ Links ]
16 M.C. Terrón, F.J.M. Verhagen, M.C.R. Franssen, J.A. Field, Chemosphere, 1998, 36, 1445-1452. [ Links ]
17 D.A. Shirley, J. Am. Chem. Soc, 1957, 79, 4922-4927. [ Links ]
18 R.G. Franz, AAPS Pharmsci, 2001, 3, 11-12. [ Links ]
19 F.J. LaRonde, M.A. Brook, Inorg. Chim. Acta., 1999, 296, 208-221. [ Links ]
20 C. Lü, B. Gao, Q. Liu, C. Qi, Colloid. Polym. Sci., 2008, 286, 553-561. [ Links ]
21 A. Samuni, D. Meisel, G. Czapski, J. Chem. Soc., Dalton Trans., 1972, 1273-1277. [ Links ]
22 M.R. Maurya, A.A. Khan, A. Azam, S. Ranjan, N. Mondal, A. Kumar, F. Avecilla, J.C. Pessoa, Dalton Trans., 2009, 39, 1345-1360. [ Links ]
23 J. Selbin, Chem. Rev., 1965, 65, 153-175. [ Links ]
24 A.D. Keramidas, S.M. Miller, O.P. Anderson, D.C. Crans, J. Am. Chem. Soc., 1997, 119, 8901-8915. [ Links ]
25 M. Bhattacharjee, M.K. Chaudhuri, N.S. Islam, P.C. Paul, Inorg. Chim. Acta., 1990, 169, 97-100. [ Links ]
26 K. Kaczorowska, Z. Kolarska, K. Mitka, P. Kowalski, Tetrahedron, 2005, 61, 8315-8327. [ Links ]
27 H. Pellissier, Tetrahedron, 2006, 62, 5559-5601. [ Links ]
28 A.G.J. Ligtenbarg A.L. Spek, R. Hage, B.L. Feringa, J. Chem. Soc., Dalton Trans., 1999, 659-661. [ Links ]
29 J. Selbin, H.R. Manning, G. Cessac, J. Inorg. Nucl. Chem., 1963, 25, 1253-1258. [ Links ]
30 Z. Wang, Y.-T. Cui, Z.-B. Xu, J. Qu, J. Org. Chem., 2008, 73, 2270-2274. [ Links ]
31 S. Lai, D.G. Lee, Synthesis, 2001, 1645-1648. [ Links ]
32 I. Hermans, J. Peeters, P.A. Jacobs, J. Org. Chem, 2007, 72, 3057-3064. [ Links ]
33 M.R. Maurya, U. Kumar, P. Manikandan, Dalton Trans., 2006, 3561-3575. [ Links ]
34 G. Rothenberg, J.H. Clark, Org. Process Res. Dev., 2000, 4, 270-274. [ Links ]
35 K. Kikushima, T. Moriuchi, T. Hirao, Tetrahedron Lett., 2010, 51, 340-342. [ Links ]
36 R.M. Totaro, P.A.M. Williams, M.C. Apella, M.A. Blesa, E.J. Baran, J. Chem. Soc., Dalton Trans., 2000, 4403-4406. [ Links ]
37 W. Zhao, h.Y. Low, P.S. Suresh, Langmuir, 2006, 22, 5520-5524. [ Links ]
Received 14 May 2010
Revised 7 July 2010
Accepted14 July 2010
* To whom correspondence should be addressed. E-mail: ryanwalmsley@gmail.com