Summary
Chiral recognition of many enantiomeric solutes by a chiral amide stationary phase is based mainly on hydrogen bonding. A chiral-recognition-factor CHI is proposed, given by the difference of the enthalpy change in the enantiomer discrimination, standardized with respect to the specific interaction of the solutes with the diamide core of the stationary phase. The röle of the entropy part is also discussed. By extrapolation of the retention behaviour to elevated temperature, peak inversion of enantiomers is predicted.
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References
E. Gil-Av, B. Feibush, R. Charles-Sigler, Tetrahedron Lett. 1966, 1009.
E. Gil-Av, J. Mol. Evol.6, 131 (1975).
C. H. Lochmüller, R. W. Souter, J. Chromatogr.113, 283 (1975).
W. A. König, J. High Resolut. Chromatogr./Chromatogr. Commun.5, 588 (1982).
E. Bayer, Z. Naturforsch.38b, 1281 (1983).
V. Schurig, Angew. Chem.96, 733 (1984); Angew. Chem. Int. Ed. Engl.23, 747 (1984).
H. Frank, G. J. Nicholson, E. Bayer, J. Chromatogr. Sci.15, 174 (1977).
E. Bayer, H. Allmendinger, G. Enderle, B. Koppenhoefer, Fresenius Z. Anal. Chem. (1985), in press.
B. Koppenhoefer, H. Allmendinger, G. Nicholson, Angew. Chem.97, 46 (1985); Angew. Chem. Int. Ed. Engl.24, (1985), in press.
B. Feibush, E. Gil-Av, Tetrahedron26, 1361 (1970).
U. Beitler, B. Feibush, J. Chromatogr.123, 149 (1976).
B. Koppenhoefer, Thesis, University of Tübingen (1980).
H. Frank, G. J. Nicholson, E. Bayer, Angew. Chem.90, 396 (1978); Angew. Chem. Int. Ed. Engl.17, 363 (1978).
W. E. Deming, Statistical Adjustment of Data, Wiley, New York, and Chapman and Hall, London (1948).
G. J. Nicholson is acknowledged for preparing the columns used. Fused silica columns coated with L- or D-Chirasil-Val are commercially available from Chrompack, Middelburg, Holland.
G. J. Nicholson, H. Frank, E. Bayer, J. High Resol. Chromatogr./Chromatogr. Commun.2, 411 (1979).
J. C. Giddings, Dynamics of Chromatography, Part I, Marcel Dekker, New York (1965).
American Society for Testing and Materials (ASTM), J. Gas Chromatogr.6, 1 (1968).
A. N. Korol, Russ. Chem. Rev.51, 698 (1982).
R. J. Laub, J. H. Purnell, P. S. Williams, M. W. P. Harbison, D. E. Martire, J. Chromatogr.155, 233 (1978).
S. Weinstein, B. Feibush, E. Gil-Av, J. Chromatogr.126, 97 (1976).
V. Schurig, Chromatographia13, 263 (1980).
V. Schurig, R. Weber, J. Chromatogr.217, 51 (1981).
B. Koppenhoefer, W. Winter, E. Bayer, Liebigs Ann. Chem. 1983, 1986.
B. Koppenhoefer, E. Bayer, J. Chromatogr. (1985), in press.
B. Giese, K. Jay, Angew. Chem.89, 482 (1977); Angew. Chem. Int. Ed. Engl.16, 466 (1977).
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Koppenhoefer, B., Bayer, E. Chiral recognition in the resolution of enantiomers by GLC. Chromatographia 19, 123–130 (1984). https://doi.org/10.1007/BF02687727
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DOI: https://doi.org/10.1007/BF02687727