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Retention characteristics of a new butylimidazolium-based stationary phase

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Abstract

A new HPLC stationary phase has been synthesized based on the ionic liquid n-butylimidazolium bromide. Imidazolium was covalently immobilized on a silica substrate through an n-alkyl tether and the retention characteristics of the resulting stationary phase were evaluated systematically. Using 28 small aromatic test solutes and reversed phase conditions, the linear solvation energy relationship approach was successfully used to characterize this new phase. The retention characteristics of the test solutes show remarkable similarity with phenyl stationary phases, despite the presence of a positive charge on the new imidazolium phase. Operated in the reversed phase mode, this new stationary phase shows considerable promise for the separation of neutral solutes and points to the potential for a truly multi-modal stationary phase.

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References

  1. Wypych G (ed) (2001) Handbook of solvents. ChemTec, Toronto

    Google Scholar 

  2. Forsyth SA, Pringle JM, MacFarlane DR (2004) Austr J Chem 57:113–119

    Article  CAS  Google Scholar 

  3. Marsh KN, Deev A, Wu AC, Tran E, Klamt A (2002) Korean J Chem Eng 19:357–362

    CAS  Google Scholar 

  4. Huddleston JG, Rogers RD (1998) Chem Commun 16:1765–1766

    Article  Google Scholar 

  5. Poole SK, Poole CF (1995) Analyst 120:289–294

    Article  CAS  Google Scholar 

  6. Yanes EG, Gratz SR, Baldwin MJ, Robison SE, Stalcup AM (2001) Anal Chem 73:3838–3844

    Article  CAS  PubMed  Google Scholar 

  7. Carda-Broch S, Berthod A, Armstrong DW (2003) Anal Bioanal Chem 375:191–199

    CAS  PubMed  Google Scholar 

  8. Adams CJ, Earle MJ, Roberts G, Seddon KR (1998) Chem Commun 19:2097–2098

    Google Scholar 

  9. Jeager DA, Tucker CE (1989) Tetrahedron Lett 37:662–664

    Google Scholar 

  10. Welton T (1999) Chem Rev 99:2071–2083

    Article  CAS  PubMed  Google Scholar 

  11. Armstrong DW, Zhang LK, He L, Ross ML (2001) Anal Chem 73:3679–3686

    CAS  PubMed  Google Scholar 

  12. Carda-Broch S, Berthod A, Armstrong DW (2003) Rapid Commun Mass Sp 17:553–560

    Article  CAS  Google Scholar 

  13. Cabovska B, Kreishman GP, Wassell DF, Stalcup AM (2003) J Chromatogr A 1007:179–187

    Article  CAS  PubMed  Google Scholar 

  14. Jiang TF, Gu YL, Liang B, Li JB, Shi YP, Ou QY (2003) Anal Chim Acta 479:249–254

    Article  CAS  Google Scholar 

  15. Qin W, Wei H, Li SFY (2003) J Chromatogr A 985:447–454

    Article  CAS  PubMed  Google Scholar 

  16. Vaher M, Koel M, Kaljurand M (2002) J Chromatogr A 979:27–32

    Article  CAS  PubMed  Google Scholar 

  17. Poole CF, Furton KG, Kersten BR (1986) J Chromatogr Sci 24:400–409

    CAS  Google Scholar 

  18. Arancibia EL, Castells RC, Nardillo AM (1987) J Chromatogr 398:21–29

    Article  CAS  Google Scholar 

  19. Furton KG, Poole CF (1987) J Chromatogr 399:47–67

    Article  CAS  Google Scholar 

  20. Anderson JL, Ding J, Welton T, Armstrong DW (2002) J Am Chem Soc 124:14247–14254

    Article  CAS  PubMed  Google Scholar 

  21. Armstrong DW, He L, Liu YS (1999) Anal Chem 71:3873–3876

    Article  CAS  PubMed  Google Scholar 

  22. Anderson JL, Armstrong DW (2003) Anal Chem 75:4851–4858

    Article  CAS  PubMed  Google Scholar 

  23. He L, Zhang W, Zhao L, Liu X, Jiang S (2003) J Chromatogr A 1007:39–45

    Article  CAS  PubMed  Google Scholar 

  24. Berthod A, Carda-Broch S (2004) Anal Bioanal Chem 380:168–177

    Article  CAS  PubMed  Google Scholar 

  25. Berthod A, Carda-Broch S (2003) J Liq Chromatogr 26:1493–1508

    Article  CAS  Google Scholar 

  26. Kamlet MJ, Taft RW (1976) J Am Chem Soc 98:377–383

    Article  CAS  Google Scholar 

  27. Kamlet MJ, Taft RW (1976) J Am Chem Soc 98:2886–2894

    Article  Google Scholar 

  28. Abraham MH (1994) Quantitative treatment of solute/solvent interactions. Elsevier, Amsterdam, pp 83–134

    Google Scholar 

  29. Abraham MH (1993) Chem Soc Rev 22:73–83

    Article  CAS  Google Scholar 

  30. Abraham MH, Chadha HS (1996) Lipophilicity in drug action and toxicology. VCH, Weinheim, pp 311–337

    Google Scholar 

  31. Bolliet D, Poole CF (1998) Anal Commun 35:253–256

    Article  CAS  Google Scholar 

  32. Poole CF (2003) The essence of chromatography. Elsevier, Amsterdam, pp 13–19

    Google Scholar 

  33. Reta M, Carr PW, Sadek PC, Rutan SC (1999) Anal Chem 71:3484–3496

    Article  CAS  PubMed  Google Scholar 

  34. Tan L, Carr PW, Abraham MH (1996) J Chromatogr A 752:1–18

    Article  CAS  Google Scholar 

  35. Tan AT, Fu G, Tomson MB, (2002) Langmuir 18:9713–9725

    Article  Google Scholar 

  36. Abraham MH (1994) J Pharm Sci 83:1085–1100

    CAS  PubMed  Google Scholar 

  37. Abraham MH (1993) J Phys Org Chem 6:660–684

    Article  CAS  Google Scholar 

  38. Stalcup AM, Martire DE, Sander LC, Wise SA (1989) Chromatographia 27:405–411

    CAS  Google Scholar 

  39. Box GEP, Hunter WG, Hunter JS (1978) Statistics for experimenters: an introduction to design, data analysis, and model building. Wiley, New York, p 587

    Google Scholar 

  40. Gottman JM (1981) Time series analysis. Cambridge University Press, Cambridge, UK, p 319

  41. Abraham MH, Roses M, Poole SK (1997) J Phys Org Chem 10:358–368

    Article  CAS  Google Scholar 

  42. Poole CF (2003) The essence of chromatography. Elsevier, Amsterdam, pp 308–312

    Google Scholar 

  43. Ståhlberg J, Almgren M (1985) Anal Chem 57:817–821

    Article  Google Scholar 

  44. Carr PW, Li J, Dallas AJ, Eikens DI, Tan LC (1993) J Chromatogr A 656:113–133

    Article  CAS  Google Scholar 

  45. Tchapla A, Heron S (1994) J Chromatogr A 684:175–188

    Article  CAS  Google Scholar 

  46. Dean TH, Jezorek JR (2004) J Chromatogr A 1028:239–245

    Article  CAS  PubMed  Google Scholar 

  47. Melander W, Stoveken J, Horvath C (1980) J Chromatogr 199:35–56

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge support from the Waters Corporation and the National Institutes of Health (GM61991-01).

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Correspondence to A. M. Stalcup.

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Sun, Y., Cabovska, B., Evans, C.E. et al. Retention characteristics of a new butylimidazolium-based stationary phase. Anal Bioanal Chem 382, 728–734 (2005). https://doi.org/10.1007/s00216-004-3051-x

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  • DOI: https://doi.org/10.1007/s00216-004-3051-x

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