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Optimization of the Synthesis of 2,6–Dinitro-4-trifluoromethylphenyl Ether Substituted Cyclodextrin Bonded Chiral Stationary Phases

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Abstract

The comparisons of five different chiral stationary phases (CSPs) based on 2,6-dinitro-4-trifluoromethylphenyl (DNP-TFM) ether substituted β-cyclodextrin are presented. The five CSPs differ from each other in the linkage/spacer chemistry, or on the position of the substituents on β-cyclodextrin, or in the sequence of the synthetic procedure. The results show that there are two optimum combinations: (1) DNP-TFM randomly substituted on the β-cyclodextrin as the chiral selector along with a carbamate linkage chain bonding it to the silica support; and (2) β-cyclodextrin derivatized by DNP-TFM substituents only on the C-2 and C-3 positions of the cyclodextrin with an ether linkage chain anchoring it to the silica gel. These two combinations show complementary separations for some enantiomers. The spacer chain effect is much more pronounced for the CSP based on the β-cyclodextrin derivatives with DNP-TFM substituents only on C-2 and C-3 positions than its randomly substituted counterpart. The sequence of derivatizing the cyclodextrin and attaching it to silica gel also affects its selectivity and efficiency. The β-cyclodextrin should be derivatized before it is linked to the silica gel.

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Acknowledgments

Support of this work by the National Institutes of Health (NIH RO1 GM53825–10), and the Iowa Energy Center is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Iowa State University, Ames, IA, 50011, USA

    Q. Zhong & W. S. Trahanovsky

  2. Advanced Separation Technologies Inc., 37 Leslie Court, P. O. Box 297, Whippany, NJ, 07981, USA

    L. He & T. E. Beesley

  3. Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX, 76019, USA

    P. Sun, C. Wang & D. W. Armstrong

Authors
  1. Q. Zhong
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  2. L. He
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  3. T. E. Beesley
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  4. W. S. Trahanovsky
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  5. P. Sun
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  6. C. Wang
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  7. D. W. Armstrong
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Correspondence to D. W. Armstrong.

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Zhong, Q., He, L., Beesley, T.E. et al. Optimization of the Synthesis of 2,6–Dinitro-4-trifluoromethylphenyl Ether Substituted Cyclodextrin Bonded Chiral Stationary Phases. Chroma 64, 147–155 (2006). https://doi.org/10.1365/s10337-006-0014-8

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  • DOI: https://doi.org/10.1365/s10337-006-0014-8

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