A new chiral stationary phase for gas chromatography by use of a chiral thiacalix[4]arene derivative

Chemistry Letters

Volumn , Issue 10, 1998, Pages 1065-1066

  Iki, Nobuhiko ^a   Narumi, Fumitaka ^a   Suzuki, Tomohiro ^a   Sugawara, Atsushi ^a   Miyano, Sotaro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032257438     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.1065     Document Type: Article

References (16)

1. S. Allenmark and V. Schurig, J. Mater. Chem., 7, 1955 (1997); S. G. Allenmark, "Chromatographic Enantioseparation. Methods and Application," Ellis Horwood, Chichester (1988); V. Schurig, Angew. Chem., Int. Ed. Engl., 23, 747 (1984).
2. S. Allenmark and V. Schurig, J. Mater. Chem., 7, 1955 (1997); S. G. Allenmark, "Chromatographic Enantioseparation. Methods and Application," Ellis Horwood, Chichester (1988); V. Schurig, Angew. Chem., Int. Ed. Engl., 23, 747 (1984).
3. S. Allenmark and V. Schurig, J. Mater. Chem., 7, 1955 (1997); S. G. Allenmark, "Chromatographic Enantioseparation. Methods and Application," Ellis Horwood, Chichester (1988); V. Schurig, Angew. Chem., Int. Ed. Engl., 23, 747 (1984).
4. V. Böhmer, Angew. Chem. Int. Ed. Engl., 1995, 34, 713; C. D. Gutsche, "Calixarenes, Monographs in supramolecular chemistry," ed by J. F. Stoddard, The Royal Society of Chemistry, Cambridge (1989); D. Diamond and M. A. McKervey, Chem. Soc. Rev., 1996, 15.
5. V. Böhmer, Angew. Chem. Int. Ed. Engl., 1995, 34, 713; C. D. Gutsche, "Calixarenes, Monographs in supramolecular chemistry," ed by J. F. Stoddard, The Royal Society of Chemistry, Cambridge (1989); D. Diamond and M. A. McKervey, Chem. Soc. Rev., 1996, 15.
6. V. Böhmer, Angew. Chem. Int. Ed. Engl., 1995, 34, 713; C. D. Gutsche, "Calixarenes, Monographs in supramolecular chemistry," ed by J. F. Stoddard, The Royal Society of Chemistry, Cambridge (1989); D. Diamond and M. A. McKervey, Chem. Soc. Rev., 1996, 15.
7. Recently, chirally modified calix[4]arenes have been utilized as a pseudostationary phase in capillary electrophoresis. Sec M. S. Peña, Y, Zhang, S. Thibodeaux, M. L. McLaughlin, A. M. de la Peña and I. M. Warner. Tetrahedron Lett., 37, 5841 (1996); M. S. Peña, Y, Zhang, and I. M. Warner, Anal. Chem., 69, 3239 (1997).
8. Recently, chirally modified calix[4]arenes have been utilized as a pseudostationary phase in capillary electrophoresis. Sec M. S. Peña, Y, Zhang, S. Thibodeaux, M. L. McLaughlin, A. M. de la Peña and I. M. Warner. Tetrahedron Lett., 37, 5841 (1996); M. S. Peña, Y, Zhang, and I. M. Warner, Anal. Chem., 69, 3239 (1997).
9. H. Kumagai, M. Hasegawa, S. Miyanari, Y. Sugawa , Y. Sato, T. Hori, S. Ueda, H. Kamiyama, and S. Miyano, Tetrahedron Lett., 38, 3971 (1997).
10. N. Iki, F. Narumi, T. Fujimoto, N. Morohashi, and S. Miyano, to be published elsewhere in near future.
11. 3).
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13. A glass capillary column (25 m × 0.25 mm i.d.) was leached with 6 M HCl at 170 °C for 12 h, deactivated with barium carbonate and statically wall-coated with a dichloromethanesolutions of (S)-4 (0.13% w/v) with OV-17 (0.08% w/v) or (S)-8 (0.23% w/v) with OV-17 (0.17% w/v). Film thickness: 0.13 μm for (S)-4 and 0.25 μm for (S)-8 coated capillaries.
14. S. Ôi, Y. Ochiai, and S. Miyano, Chem. Lett., 1991, 1575, and literatures cited therein.
15. Retention data for l-phenylethylalcohol: k' = 14.782, α = 1.012 at 90 °C. For l-phenylethylamine: k' = 4.491, α = 1.000 at 100 °C. Each on (S)-4-coated column.
16. No direct comparison of the thermostability between (S)-4- and CD-coated columns has been attempted The maximum allowable operating temperatures of commercially available CD columns range from 180 to 250 °C depending upon the functional groups introduced into CDs. Sec "CHIRALDEXTM Hand Book. A Guide to Using Cyclodextrin Bonded Phases for Chiral Separations by Capillary Gas Chromatography," 5th ed , Advanced Separation Technologies Inc., Whippany (1996).