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HPLC Separation of the atropisomers of some substitutedN-Arylthiazoline-2-Thiones withγ-Cyclodextrin as a chiral mobile phase additive: Size and lipophilicity effects of substitutents

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Abstract

The chromatographic separations of some substitutedN-arylthiazoline-2-thione atropisomers are described, using reversed-phase HPLC withγ-cyclodextrin as a chiral mobile phase additive. The effects of the size and lipophilicity of various substituents are discussed and emphasize the close relationship between inclusion inside the cyclodextrin cavity and the chromatographic selectivity.

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References

  1. E. Smolkova-Keulemansova, L. Fetl and J. Snopek: ‘Cyclodextrins and their derivatives in modern analytical high-performance separation methods’ (Minutes Int. Symp. Cyclodextrins, 5th, Ed. D. Duchêne), pp. 617–622, Ed. Santé, Paris, Fr. (1990).

    Google Scholar 

  2. S. Li and W.C. Purdy:Chem. Rev. 92, 1457 (1992).

    Google Scholar 

  3. R. Kuhn, F. Stoecklin and F. Erni:Chromatographia 33, 32 (1992).

    Google Scholar 

  4. R.A. Menges and D.W. Armstrong: ‘Chiral separations using native and functionalized cyclodextrin-bonded phases in high-pressure liquid chromatography’ (ACS Symp. Ser. 471 (Chiral Sep. Liq. Chromatogr.), Ed. S. Ahuja), pp. 67–100 (1991).

  5. A. Walhagen and L.E. Edholn:Chromatographia 32, 215 (1991).

    Google Scholar 

  6. C. Roussel and A. Favrou:Chirality 5, 471 (1993)

    Google Scholar 

  7. C. Roussel, M. Adjimi, A. Chemlal and A. Djafri:J. Org. Chem. 53, 5076 (1988).

    Google Scholar 

  8. C. Roussel, J.L. Stein and F. Beauvais:New J. Chem. 14, 169 (1990).

    Google Scholar 

  9. C. Roussel, J.L. Stein, M. Sergent and R. Phan Tan Luu: Attempts to quantify the effect of selected structural parameters on the separation of someN-arylthiazoline-2-thione andN-arylthiazolin-2-one stropisomers on the chiral stationary phase, cellulose triacetate (CTA1) (Recent Advances in Chiral Separations), Eds. D. Stevenson and I.D. Wilson), pp. 105–108, Plenum, N.Y. (1991).

    Google Scholar 

  10. C. Roussel, S. Lehuédé, C. Popescu and J.-L. Stein:Chirality 5, 207 (1993).

    Google Scholar 

  11. C. Roussel and A. Chemlal:New J. Chem. 12, 947 (1988).

    Google Scholar 

  12. J. Cohen and J.L. Lach:J. Pharm. Sci. 52, 132 (1963).

    Google Scholar 

  13. T. Miyaji, Y. Kurono, K. Uekama and K. Ikeda:Chem. Pharm. Bull. 24, 1155 (1976)

    Google Scholar 

  14. K.A. Connors:Binding constants: A Measurement of Molecular Complex Stability, John Wiley & Sons, New York (1987).

    Google Scholar 

  15. F. Cramer, W. Saenger and H.Ch. Spatz:J. Am. Chem. Soc. 89, 14 (1967).

    Google Scholar 

  16. S. Hamai:J. Phys. Chem. 93, 2074 (1989).

    Google Scholar 

  17. Y. Matsui and K. Mochida:Bull. Chem. Soc. Jpn. 52, 2808 (1979).

    Google Scholar 

  18. A. Buvari, J. Szejtli and L. Barcza:J. Incl. Phenom. 1, 151 (1983).

    Google Scholar 

  19. G. Patonay, K. Fowler, G. Nelson and I.M. Warner:Anal. Chim. Acta 207, 251 (1988).

    Google Scholar 

  20. A. Munoz de la Pena, V.C. Anigbogu, T.T. Ndou and I.M. Warner:Anal. Chem. 63, 1018 (1991).

    Google Scholar 

  21. K. Uekama, F. Hirayama, S. Nasu, N. Matsuo and T. Irie:Chem. Pharm. Bull. 26, 2477 (1978).

    Google Scholar 

  22. J. Zukowski, D. Sybilska and J. Jurczak:Anal. Chem. 57, 2215 (1985).

    Google Scholar 

  23. K. Fujimura, T. Ueda, M. Kitagawa, H. Takayanagi and T. Ando:Anal. Chem. 58, 2668 (1986)

    Google Scholar 

  24. R.M. Mohseni and R.J. Hurtubise:J. Chromatogr. 499, 395 (1990)

    Google Scholar 

  25. V.C. Anigbogu, A. Munoz de la Pena, T.T. Ndou and I.M. Warner:Anal. Chem. 64, 484 (1992).

    Google Scholar 

  26. W.L. Hinze:Sep. Pur. Methods 10, 159 (1981).

    Google Scholar 

  27. K. Csabai, T. Cserhati, J. Szejtli and J. Bojarski: ‘Complexation of barbiturates with hydroxypropylβ-cyclodextrin (Minutes Int. Symp. Cyclodextrins, 5th, Ed. D. Duchêne), pp. 234–238, Ed. Santé, Paris, Fr. (1990).

    Google Scholar 

  28. R. Furuta and H. Nakazawa:J. Chromatogr. 625, 231 (1992).

    Google Scholar 

  29. K. Belsner, M. Pfeifer and B. Wilffert:J. Chromatogr. 629, 123 (1993).

    Google Scholar 

  30. D. Sybilska, J. Debowski, J. Jurczak and J. Zukowski:J. Chromatogr. 286, 163 (1984).

    Google Scholar 

  31. J. Debowski and D. Sybilska:J. Chromatogr. 353, 409 (1986).

    Google Scholar 

  32. M. Gazdag, G. Szepesi and L. Huszar:J. Chromatogr. 351, 128 (1986).

    Google Scholar 

  33. H. Weems and K. Zamani:Chirality 4, 268 (1992).

    Google Scholar 

  34. Y.K. Tan and S.J. Soldin:J. Chromatogr. (Biomed. Applic.)422, 187 (1987).

    Google Scholar 

  35. S.C. Chang, L.R. Wang and D.W. Armstrong:J. Liq. Chromatogr. 15, 1411 (1992).

    Google Scholar 

  36. A.F. Casy, A.D. Cooper, T.M. Jefferies, R.M. Gaskell, D. Greatbanks and R. Pickford:J. Pharm. Biomed. Anal. 7, 787 (1991).

    Google Scholar 

  37. M.J.M. Wells and C.R. Clark:Anal. Chem. 53, 1341 (1981).

    Google Scholar 

  38. L.A. Bylshak, K.Y. Dodson, G. Patonay, I.M. Warner and W.E. May:Anal. Chem. 61, 955 (1989).

    Google Scholar 

  39. N. Thuaud, B. Sebille, A. Deratani and G. Lelièvre:J. Chromatogr. 503, 453 (1990).

    Google Scholar 

  40. M.L. Bender and M. Komiyama:Cyclodextrin Chemistry, Springer-Verlag, New York (1978).

    Google Scholar 

  41. W. Saenger:Angew. Chem. Int. Ed. Engl. 19, 344 (1980).

    Google Scholar 

  42. E. Smolkova-Keulemansova and S. Krysl:J. Chromatogr. 184, 347 (1980).

    Google Scholar 

  43. W.L. Hinze:Sep. Purif. Methods 10, 159 (1981).

    Google Scholar 

  44. E. Smolkova-Keulemansova:J. Chromatogr. 251, 17 (1982).

    Google Scholar 

  45. K.B. Lipkowitz, K.M. Green, J.A. Yank, G. Pearl and M.A. Peterson:Chirality 5, 51 (1993).

    Google Scholar 

  46. W.S. Kennth:J. Liq. Chromatogr. 10, 655 (1987).

    Google Scholar 

  47. C. Roussel, M. Chanon and R. Barone: ‘Mercapthiazoles, Hydroxythiazoles and their derivatives’ (Thiazole and its Derivatives), Vol. 2, Part VII, Ed. J. Metzger), pp. 369–559, Wiley, N.Y. (1979).

    Google Scholar 

  48. J. Debowski, J. Jurczak and D. Sybilska:J. Chromatogr. 282, 83 (1983).

    Google Scholar 

  49. C. Bertucci, E. Domenici, G. Uciello-Baretta and P. Salvadori:J. Chromatogr. 506, 617 (1990).

    Google Scholar 

  50. T. Jira, C. Vogt, G. Blaschke and Th. Beyrich:Pharmazie 48H3, 196 (1993).

    Google Scholar 

  51. J. Debowski and D. Sybilska:J. Chromatogr. 353, 409 (1986).

    Google Scholar 

  52. C. Vecchi, A. Naggi and G. Torri: ‘Inclusion complexes of naphthols with cyclodextrins in aqueous solution. A proton NMR study’ (Proc. Int. Symp. Cyclodextrins, 4th, Eds. O. Huber and J. Szejtli), pp. 215–219, Kluwer, Dordrecht, Nethy. (1988).

    Google Scholar 

  53. T. Takeuchi:J. High Res. Chromatogr. 14, 560 (1991).

    Google Scholar 

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Roussel, C., Favrou, A. HPLC Separation of the atropisomers of some substitutedN-Arylthiazoline-2-Thiones withγ-Cyclodextrin as a chiral mobile phase additive: Size and lipophilicity effects of substitutents. J Incl Phenom Macrocycl Chem 16, 283–296 (1993). https://doi.org/10.1007/BF00708798

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