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Synthesis and characterization of new organometallic complexes bonded stationary phases for high-performance liquid chromatography

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Summary

The preparation, characterization and potential liquid chromatographic applications of various organometallic iron complexes silica stationary phases are presented. These new supports are synthesized by covalently linking ferrocene, as well as some of its cationic derivatives, to appropriately derivatized silica support matrices. These columns exhibit moderate to high selectivity towards the separation of polycyclic aromatic hydrocarbons (PAHs). A charge transfer retention mechanism has been proposed. A comparison with a reference stationary phase, 3,5-dinitrobenzamide (DNB), to quantify the acceptor power of the new stationary bonded phases, is also reported. Finally, the effect of varying the derivatives of the bonded metallocene on PAHs retention is discussed.

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References

  1. Kirkland, J.J.,Modern Practice of Liquid Chromatography 1971, John Wiley J.J. & Sons, New York.

    Google Scholar 

  2. Snyder, L.R.; Kirkland, J.J.Introduction to Modern Liquid Chromatography 1971, John Wiley & Sons, New York.

    Google Scholar 

  3. Kibbey, C.E.; Meyerhoff, M.E.J. Chromatogr. 1974,641, 49.

    Article  Google Scholar 

  4. Forster, R.Organic Charge-Transfer Complexes 1966, Academic Press, London, New York.

    Google Scholar 

  5. Person, W.B.; Mulliken, R.S.Molecular Complexes 1969, Wiley & Sons, New York.

    Google Scholar 

  6. Forster, R.Molecular Association 1979, Academic Press, London, New York, San Francisco.

    Google Scholar 

  7. Paetzold, R.Zeit. Chem. 1975,15, 377.

    CAS  Google Scholar 

  8. Morokura, K.Acc. Chem. Res. 1977,10, 294.

    Article  Google Scholar 

  9. Holstein, W.; Hemetsberger, H.Chromatographia 1982,15, 186.

    Article  CAS  Google Scholar 

  10. Holstein, W.; Hemetsberger, H.Chromatographia 1982,15, 251.

    Article  CAS  Google Scholar 

  11. Félix, G.; Bertrand, C.;Analusis 1989,17, 326.

    Google Scholar 

  12. Félix, G.; Thienpont, A.; Dentraygues, P.Chromatographia 1992,34, 177.

    Article  Google Scholar 

  13. Cagniant, D.; Davankov, V.A.; Félix, G.; Nondek, L. inComplexation Chromatography. Cagniant, D., Ed.,Chromatogr. Sci. Ser.,1991,57.

  14. Mifune, M.; Kanai, T.; Urabe, M.; Iwado, A., Haginaka, J.; Motohashi, N.; Saito, Y.Anal. Sci. 1999,15, 581; b) Mifune, M.; Onoda, M.; Takatsuki, T.; Kanai, T.; Iwado, A.; Motohashi, N.; Haginaka, J.; Saito, Y.Chem. Pharm. Bull. 1999,47, 346; c) Mifune, M.; Mori, Y.; Onoda, M.; Iwado, A.; Motohashi, N.; Haginaka, J.; Saito, Y.Anal. Sci. 1998,14, 1127.

    Article  CAS  Google Scholar 

  15. Xiao, J.; Kibbey, C.E.; Coutant, D.E.; Martin, G.B.; Meyerhoff, M.E.,J. Liq. Chrom. Rel. Technol. 1996,19, 2901.

    CAS  Google Scholar 

  16. Deeming, A.J. InComprehensive Organometallic Chemistry 1982,4, 377. Wilkinson, G.; Stone, F.L.; Abel, E. Eds, Pergamon Press, Oxford.

    Google Scholar 

  17. Green, M.L.H.,Organometallic Compounds 1968,II: The Transition Elements, Methuen, London; b) Collman, J.P.: Hedegus, L.S.Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, 1980; c) Cotton, F.A.; Wilkinson, G.Advanced Inorganic Chemistry 1980, 4th ed., John & Sons Wiley, New York.

    Google Scholar 

  18. Marr, G.; Rockett, B.W.J. Organomet. Chem. 1982,227, 373.

    Article  CAS  Google Scholar 

  19. Cass, A.E.G.; Davis, G.; Francis, G.D.; Hill, H.A.O.; Higgins, I.J.; Aston, W.J.; Plotkin, E.V.; Scott, L.D.; Turner, A.P.F.Anal. Chem. 1984,56, 667.

    CAS  Google Scholar 

  20. Cass, A.E.G.; Davis, G.; Hill, H.A.O.; Higgins, I.J.; Plotkin, E.V.; Turner, A.P.F.; Aston, W.J. InCharge and Field Effects in Biosystems 1984, 475; Allen, N.J.; Usherwood, P.N.R., Eds, Abacus Press, Tumbridge Wells.

    Google Scholar 

  21. Astruc, D.Tetrahedron 1983,39, 4027.

    Article  CAS  Google Scholar 

  22. Astruc, D.Top. Curr. Chem. 1991,160, 49.

    Google Scholar 

  23. Nicholls, B.; Whiting, M.C.J. Chem. Soc. 1959,551; b) Semmelack, M.F.Annals, N.Y. Acad. Sci. 1977,295, 26; c) Jaouen, G.Annals, N.Y. Acad. Sci. 1977,295, 59; d) Bunnett, J.F.; Hermann, H.J. Org. Chem. 1971,36, 4081.

  24. Khand, I.U.; Pauson, P.L.; Watts, W.F.J. Chem. Soc. C 1968, 2261; b) Piorko, A.; Abd-El-Aziz, A.S.; Lee, C.C.; Sutherland, R.G.J. Chem. Soc. 1989,Perkin Trans. 1, 469; c) Lee, C.C.; Gill, U.S.; Iqbal, M.; Azogu, C.I.; Sutherland, R.G.J. Organometal. Chem. 1982,231, 151; d) Sutherland, R.G.J. Organometal. Chem. Libr. 1977,3, 311; e) Sutherland, R.G.; Iqbal, M.; Piorko, A.J. Organometal. Chem. 1986,302, 307; f) Abd-El-Aziz, A.S.; Lee, C.C.; Piorko, A.; Sutherland, R.G.J. Organometal. Chem. 1988,348, 95.

  25. Nesmeyanov, A.N.; Reutov, O.A.Dokl. Akad. Nauk SSSR 1957,115, 518; Lau, H.H.; Hart, H.J. Org. Chem. 1959,24, 280; b) Katada, T.; Nishida, M.; Kato, S.; Mizuta, M.J. Organomet. Chem. 1977,129, 189; c) Rosenblum, M.Chemistry of the Iron Group Metallocenes;1965, John Wiley & Sons, New York, Part. I; d) Nesmeyanov, A.N.; Vol’kenau, N.A.; Bolesova, I.N.Dokl. Akad. Nauk SSSR 1963,149, 615 and1966,166, 607; e) Nesmeyanov, A.N.Adv. Organomet. Chem. 1972,10, 1; f) Nesmeyanov, A.N.; Vol’kenau, N.A.; Bolesova, I.N.Dokl. Akad. Nauk SSSR 1967,1975, 606; g) Nesmeyanov, A.N.; Vol’kenau, N.A.; Isaeva, L.S.; Bolesova, I.N.Dokl. Akad. Nauk SSSR 1968,183, 354 and1967,176, 106; h) Nesmeyanov, A.N.; Vol’kenau, N.A.; Sirotkina, E.I.; Deryabin, V.V.Dokl. Akad. Nauk SSSR 1967,177, 1110.

    CAS  Google Scholar 

  26. Rosset, R.; Caude, M.; Jardy, A.Chromatographies en Phases Liquide et Supercritique 1991, ed. Masson, Paris, Milan, Barcelonne, Bonn.

    Google Scholar 

  27. Shriver, D.F.The manipulation of Air-Sensitive Compounds 1969, McGraw-Hill, New-York.

    Google Scholar 

  28. Coffield, T.H.; Sandel, V.; Closson, R.D.J. Am. Chem. Soc. 1957,79, 5826.

    Article  CAS  Google Scholar 

  29. Guerchais, V.; Roman, E.; Astruc, D.Organometallics 1986,5, 2505.

    Article  CAS  Google Scholar 

  30. Linton, R.W.; Miller, M.L.; Maciel, G.E.; Hawkins, B.L.Surf. Interface Anal. 1985,7, 196; b) Miller, M.L.; Linton, R.W.; Bush, S.G.; Jorgenson, J.W.Anal. Chem. 1984,56, 2204; c) Miller, M.L.; Linton, R.W.Anal. Chem. 1985,57, 2314.

    Article  CAS  Google Scholar 

  31. Buszewski, B.Chromatographia 1990,29, 233; b) Brown, V.A.; Barrett, D.A.; Shaw, P.A.; Davies, M.C.; Ritchie, H.J.; Ross, P.; Paul, A.J.; Watts, J.F.Surf. Interface Anal. 1994,21, 263.

    Article  CAS  Google Scholar 

  32. Mose, P.R.; Murray, R.M.J. Electroanal. Chem. 1977,77, 393.

    Google Scholar 

  33. Bordelanne, O.; Delville, M.H.; Labrugère, C. work in progress.

  34. Mifune, M.; Shimomura, Y.; Mori, Y.; Onoda, M.; Iwado, A.; Motohashi, N.; Haginaka, J.; Saito, Y.Bull. Chem. Soc. Jpn. 1998,71, 1825; b) Silva, C.R.; Jardim, I.C.S.F.; Airoldi, C.J. High Resol. Chromatogr. 1999,22, 103.

    Article  CAS  Google Scholar 

  35. Félix, G.; Bertrand, C.HRC & CC 1984,7, 160.

    Google Scholar 

  36. Bordelanne, O.; Delville, M.H.; Félix, G. unpublished results.

  37. Togni, A.; Hayashi, T.Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Sciences 1995, VCH-Wiley, Weinheim, New-York.

    Google Scholar 

  38. Davies, S.G.; Green, M.L.H.; Mingos, D.M.P.,Tetrahedron 1978,34, 3047.

    Article  CAS  Google Scholar 

  39. Warren, K.D.Struct. Bond. 1976,27, 45; b) Clark, D.W.; Warren, K.D.Struct. Bond. 1980,27, 45; c) Anderson, S.F. Jr; Drago, R.S.J. Am. Chem. Soc. 1970,92, 4244;Inorg. Chem. 1972,11, 1564.

    CAS  Google Scholar 

  40. Bertrand-Motard, C.Thesis 1988, University of Bordeaux I.

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Bordelanne, O., Delville, M.H., Félix, G. et al. Synthesis and characterization of new organometallic complexes bonded stationary phases for high-performance liquid chromatography. Chromatographia 52, 51–57 (2000). https://doi.org/10.1007/BF02490792

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