Temperature-induced inversion of the elution order of enantiomers in gas chromatography: N-ethoxycarbonyl propylamides and N-trifluoroacetyl ethyl esters of α-amino acids on Chirasil-Val-C11 and Chirasil-Dex stationary phases

Analytical Chemistry

Volumn 79, Issue 12, 2007, Pages 4401-4409

  Levkin, Pavel A ^a   Levkina, Anna ^a   Czesla, Harri ^a   Schurig, Volker ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ENTHALPY ENTROPY COMPENSATION; ISOENANTIOSELECTIVE TEMPERATURE; PROPYLAMIDES; TEMPERATURE INDUCED INVERSION;

AMINO ACIDS; ENANTIOSELECTIVITY; ENTHALPY; ESTERS; GAS CHROMATOGRAPHY; POLYAMIDES;

ENANTIOMERS;

ALANINE; ALPHA AMINO ACID; AMIDE; AMINO ACID DERIVATIVE; N ETHOXYCARBONYLPROPYLAMIDE DERIVATIVE; N TRIFLUOROACETYL ETHYL ESTER DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG; VALINE;

ARTICLE; CHIRALITY; ELUTION; ENANTIOMER; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; RACEMIC MIXTURE; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE; THERMODYNAMICS;

AMIDES; AMINO ACIDS; CHROMATOGRAPHY, GAS; CYCLODEXTRINS; ENTROPY; ORGANIC CHEMICALS; SENSITIVITY AND SPECIFICITY; SILOXANES; STEREOISOMERISM; TEMPERATURE;

EID: 34347258893     PISSN: 00032700     EISSN: None     Source Type: Journal    
DOI: 10.1021/ac062064j     Document Type: Article

References (22)

1. Schurig, V. Chirality 2005, 17, S205-S226.
2. Kurganov, A. A.; Zhuchkova, L. Y.; Davankov, V. A. J. Inorg. Nucl. Chem. 1978, 40, 1081-1083.
3. Koppenhoefer, B.; Bayer, E. Chromatographia 1984, 19, 123.
4. Hess, H.; Burger, G.; Musso, H. Angew. Chem. 1978, 90, 645.
5. Watabe, K.; Charles, R.; Gil-Av, E. Angew. Chem. 1989, 101, 194.
6. Schurig, V.; Ossig, J.; Link, R. Angew. Chem. 1989, 101, 197-198.
7. König, W. A.; Icheln, D.; Hardt, L. J. High Resolut. Chromatogr. 1991, 14, 694-695.
8. Koppenhoefer, B.; Bingcheng, L.; Muschalek, V.; Trettin, U.; Willisch, H.; Bayer, E. In Proceedings of the 20th European Peptide Symposium; Tübingen, Germany, 1988.
9. König, W. A.; Icheln, D.; Runge, T.; Pfaffenberger, B.; Ludwig, P.; Huehnerfuss, H. J. High Resolut. Chromatogr. 1991, 14, 530-536.
10. Benicka, E.; Krupcik, J.; Spanik, I.; Hrouzek, J.; Sandra, P. J. Microcolumn Sep. 1996, 8, 57-65.
11. Beck, T.; Liepe, J.-M.; Nadzik, J.; Rohn, S.; Mosandl, A. J. High Resolut. Chromatogr. 2000, 23, 569-575.
12. Maas, B.; Dietrich, A.; Beck, T.; Boerner, S.; Mosandl, A. J. Microcolumn Sep. 1995, 7, 65.
13. Kobor, F.; Schomburg, G. J. High Resolut. Chromatogr. 1993, 16, 693-699.
14. Schurig, V.; Betschinger, F. Chem. Rev. 1992, 92, 873-888.
15. Fulde, K.; Frahm, A. W. J. Chromatogr., A 1999, 858, 33-43.
16. Schlauch, M.; Frahm, A. W. Anal. Chem. 2001, 73, 262-266.
17. Feibush, B. J. Chem. Soc., Chem. Commun. 1971, 11, 544-545.
18. Feibush, B.; Gil-Av, E. Tetrahedron 1970, 26, 1361-1368.
19. Walser, M. Dissertation, University of Tuebingen, 1987.
20. Levkin, P. A.; Levkina, A.; Schurig, V. Anal. Chem. 2006, 78, 5143-5148.
21. Abe, I.; Kawazuma, M.; Fujimoto, N.; Nakahara, T. Chem. Lett. 1995, 329-330.
22. Abe, I.; Nakahara, T. J. High Resolut. Chromatogr. 1996, 19, 511-514.