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Licensed Unlicensed Requires Authentication Published by De Gruyter May 2, 2008

Complexes of transition metals bonded to silica via β-diketonate groups — synthesis, structure, and catalytic activity

  • Iwona Rykowska EMAIL logo and Włodzimierz Urbaniak
From the journal Chemical Papers

Abstract

Transition metal complexes bonded to silica via silanes with β-diketonate groups can be used as packings for complexation gas chromatography or as immobilized homogenous metal complex catalysts. On basis of elemental analysis and the determination of surface area, possible structures of the complexes formed on the silica surface have been proposed. The possibility of using the immobilized complexes as catalysts has been indicated. Especially nickel complexes were taken into consideration. These immobilized complexes were used previously as packings for complexation gas chromatography.

[1] Allum, K. G., Hancock, R. D., Howell, I. V., Lester, T. E., McKenzie, S., Pitkethly, R. C., & Robinson, P. J. (1976). Supported transition metal complexes V.: Liquid phase catalytic hydrogenation of hexene-1, cyclohexane and isoprene under continuous flow conditions. Journal of Catalysis, 43, 331–338. DOI: 10.1016/0021-9517(76)90318-3. http://dx.doi.org/10.1016/0021-9517(76)90318-310.1016/0021-9517(76)90318-3Search in Google Scholar

[2] Berendsen, G. E., Pikaart, K. A., & de Galon, L. (1980). Preparation of various bonded phases for HPLC using monochlorosilanes. Journal of Liquid Chromatography, 3, 1437–1464. http://dx.doi.org/10.1080/0148391800806278810.1080/01483918008062788Search in Google Scholar

[3] Buszewski, B., Jezierska, M., Welniak, M., & Berek, D. (1998). Survey and tretrends in the preparation of chemically bonded silica phases for liquid chromatographic analysis. Journal of High Resolution Chromatography, 21, 267–281. DOI: 10.1002/(SICI)1521-4168(19980501)21:5〈267::AID-JHRC267〉3.0.CO;2-7. http://dx.doi.org/10.1002/(SICI)1521-4168(19980501)21:5<267::AID-JHRC267>3.0.CO;2-710.1002/(SICI)1521-4168(19980501)21:5<267::AID-JHRC267>3.0.CO;2-7Search in Google Scholar

[4] Cagniant, D. (1992). Complexation chromatography. New York: Marcel Dekker. Search in Google Scholar

[5] Čapka, M., Czakoová, M., Urbaniak, W., & Schubert, U. (1992). Hydrogenation and hydrosilylation activity of homogeneous and immoblilized dicarbonyl(2,4-pentanedionato)rhodium complexes. Journal of Molecular Catalysis, 74, 335–344. DOI: 10.1016/0304-5102(92)80251-B. http://dx.doi.org/10.1016/0304-5102(92)80251-B10.1016/0304-5102(92)80251-BSearch in Google Scholar

[6] Charles, G., & Pawlikowski, N. A. (1958). Comparative heat stabilities of some metal acetylacetonate chelates. Journal of Physical Chemistry, 62, 440–444. DOI: 10.1021/j150562a017. http://dx.doi.org/10.1021/j150562a01710.1021/j150562a017Search in Google Scholar

[7] Gao, H., & Angelici, R. J. (1999). Rhodium-phosphine complex catalysts tethered on silica-supported heterogeneous metal catalysts: arene hydrogenation under atmospheric pressure. Journal of Molecular Catalysis A, 149, 63–74. DOI: 10.1016/S1381-1169(99)00182-X. http://dx.doi.org/10.1016/S1381-1169(99)00182-X10.1016/S1381-1169(99)00182-XSearch in Google Scholar

[8] Hartley, F. T. (1985). Supported metal complexes. Dordrecht: Reidel. 10.1007/978-94-009-5247-8Search in Google Scholar

[9] Lindener, E., Auer, F., Baumann, A., Wegner, P., Mayer, H. A., Bertagnalli, H., Reinöhl, U., Ertel, T. S., & Weber, A. (2000). Supported organometallic complexes (part XX.): Hydroformylation of olefins with rhodium(I) hybrid catalysts. Journal of Molecular Catalysis A, 157, 97–109. DOI: 10.1016/S1381-1169(00)00038-8. http://dx.doi.org/10.1016/S1381-1169(00)00038-810.1016/S1381-1169(00)00038-8Search in Google Scholar

[10] Maciejewski, H., Marciniec, B., & Kownacki, I. (2000). Catalysis of hydrosilylation (part XXXIV.): High catalytic efficiency of the nickel equivalent of Karstedt catalyst. Journal of Organometalic Chemistry, 597, 175–181. DOI: 10.1016/S0022-328X(99)00685-3. http://dx.doi.org/10.1016/S0022-328X(99)00685-310.1016/S0022-328X(99)00685-3Search in Google Scholar

[11] Marciniec, B., & Maciejewski, H. (1993). Catalysis of hydrosilylation (part XXIII.): Effect of substituents at silicon on unusual hydrosilylation of vinylsilanes catalysed by nickel acetylacetonate. Journal of Organometalic Chemistry, 454, 45–50. DOI: 10.1016/0022-328X(93)83221-G. http://dx.doi.org/10.1016/0022-328X(93)83221-G10.1016/0022-328X(93)83221-GSearch in Google Scholar

[12] Marciniec, B., Maciejewski, H., & Rosenthal, U. (1994). Catalysis of hydrosilylation (part XXV.): Effect of nickel(0) and nickel(II) complex catalysts on dehydrogenative silylation, hydrosilylation and dimerization of vinyltriethoxysilane. Journal of Organometalic Chemistry, 484, 147–151. DOI: 10.1016/0022-328X(94)87198-1. http://dx.doi.org/10.1016/0022-328X(94)87198-110.1016/0022-328X(94)87198-1Search in Google Scholar

[13] Marciniec, B., Maciejewski, H., Guliński, J., Maciejewska, B., & Duczmal, W. (1996). Competitive dehydrogenative silylation and hydrogenative dimerization of vinyltriethoxysilane catalysed by the (Ni(acac)2+PPh3) system, intermediate and mechanistic implications. Journal of Organometalic Chemistry, 521, 245–251. DOI: 10.1016/0022-328X(96)06355-3. http://dx.doi.org/10.1016/0022-328X(96)06355-310.1016/0022-328X(96)06355-3Search in Google Scholar

[14] Marciniec, B. (2005). Catalysis bytransition metal complexes of alkene silylation-recent progress and mechanistic implications. Coordination Chemistry Reviews, 249, 2374–2390. DOI: 10.1016/j.ccr.2005.02.025. http://dx.doi.org/10.1016/j.ccr.2005.02.02510.1016/j.ccr.2005.02.025Search in Google Scholar

[15] Mehrotra, R. C., Bohra, R., & Gaur, D. P. (1978). Metal β-diketonates and allied derivatives. London: Academic Press. Search in Google Scholar

[16] Michalska, Z. M., Ostaszewski, B., Strzelec, K., Kwiatkowski, R., & Włochowicz, A. (1994). Selectivity of polyamide-supported rhodium catalysts in the addition of hydrosilanes to vinyl compounds. Reactive Polymers, 23, 85–93. DOI: 10.1016/0923-1137(94)90005-1. http://dx.doi.org/10.1016/0923-1137(94)90005-110.1016/0923-1137(94)90005-1Search in Google Scholar

[17] Novak, J., Buszewski, B., & Berek, D. (1990). Influence of pore structure of silica packing on HPLC column characteristics. Chemical Papers, 44, 31–43. Search in Google Scholar

[18] Panster, P., & Wieland, S. (1996). Immobilization. In B. Cornils, & W. A. Herrmann (Eds.), Applied homogenous catalysis with organometallic compounds (pp. 646–663). Weinheim: VCH. Search in Google Scholar

[19] Picker, J. E., & Stevens, R. E. (1981). Lanthanide metal chelates as selective complexing sorbents for gas chromatography. Journal of Chromatography, 203, 29–40. DOI 10.1016/S0021-9673(00)80279-4. http://dx.doi.org/10.1016/S0021-9673(00)80279-410.1016/S0021-9673(00)80279-4Search in Google Scholar

[20] Pool, C. F., & Pool, S. K. (1992). Chromatography today. Amsterdam: Elsevier. Search in Google Scholar

[21] Rykowska, I., & Wasiak, W. (2003). The synthesis and characterisation of chemically bonded stationary phases for gas chromatography. Properties of silica modified with Cu(II) and Cr(III) complexes. Chemia Analityczna, 48, 495–507. Search in Google Scholar

[22] Siedle, A. R. (1987). Diketones and related ligands. In G. Wilkinson, R. D. Gillard, & J. A. McClaverty (Eds.), Comprehensive Coordination Chemistry (Vol. 2, Chapter 15.4). Oxford: Pergamon Press. Search in Google Scholar

[23] Urbaniak, W., & Schubert, U. (1991). An efficient synthesis of R3Si(CH2)n-substituted acetylacetone derivatives. Liebigs Annalen der Chemie, 11, 1221–1223. DOI: 10.1002/jlac.1991199101209. http://dx.doi.org/10.1002/jlac.199119910120910.1002/jlac.1991199101209Search in Google Scholar

[24] Vansant, E. F., Van Der Voort, P., & Vrancken, K. L. (1995). Characterization and chemical modification of the surface. Amsterdam: Elsevier. http://dx.doi.org/10.1016/S0167-2991(06)81508-910.1016/S0167-2991(06)81508-9Search in Google Scholar

[25] Wasiak, W., Urbaniak, W., Obst, I., & Wawrzyniak, R. (1992). Synthesis of silane with beta-diketonate group and their application in modification of silica gel for complexation gas chromatography. Acta Chromatographica, 1, 56–68. Search in Google Scholar

[26] Wasiak, W., & Rykowska, I. (1996). Chemically bonded chelates as selective complexing sorbents for gas chromatography. Silica surface modified with Co(II) and Ni(II) complexes. Journal of Chromatography, 723, 313–324. DOI 0021-9673(95)00872-1. http://dx.doi.org/10.1016/0021-9673(95)00872-110.1016/0021-9673(95)00872-1Search in Google Scholar

[27] Wasiak, W., & Rykowska, I. (1998). Charge-transfer interaction between nucleofilic compounds and chromatographic packing containing chemically bonded Cu(II) complexes. Chromatographia, 48, 284–292. DOI: 10.1007/BF02467684. http://dx.doi.org/10.1007/BF0246768410.1007/BF02467684Search in Google Scholar

[28] Wasiak, W., & Rykowska, I. (1999). Iminoketonate complexes of Cu(II) chemically bonded to silica in gas chromatography. Analytica Chimica Acta, 378, 101–109. DOI: 10.1016/S0003-2670(98)00567-4. http://dx.doi.org/10.1016/S0003-2670(98)00567-410.1016/S0003-2670(98)00567-4Search in Google Scholar

[29] Wasiak, W., & Wawrzyniak, R. (2005). Ketoimine modified silica as an adsosbent for gas chromatographic analysis of olefins. Journal of Separation Science, 28, 2454–2462. DOI 10.1002/jssc.200400035. http://dx.doi.org/10.1002/jssc.20040003510.1002/jssc.200400035Search in Google Scholar

[30] Wenzel, T. H., Bonasia, P. J., & Brewitt, T. (1989). Application of metal β-diketonate polymers as selective sorbents in complex mixtures. Journal of Chromatography, 463, 171–176. DOI: 10.1016/S0021-9673(01)84466-6. http://dx.doi.org/10.1016/S0021-9673(01)84466-610.1016/S0021-9673(01)84466-6Search in Google Scholar

[31] Werner, H., & Möhring, U. (1994). Supported rhodiumcatalysts: new aspects in the formulation of trisubstituted olefins from simple alkenes and diazoalkanes. Journal of Organometallic Chemistry, 475, 277–282. DOI: 10.1016/0022-328X(94)84032-6. http://dx.doi.org/10.1016/0022-328X(94)84032-610.1016/0022-328X(94)84032-6Search in Google Scholar

Published Online: 2008-5-2
Published in Print: 2008-6-1

© 2008 Institute of Chemistry, Slovak Academy of Sciences

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