Peak separation by adventitious or added water in normal-phase chiral HPLC

Journal of Organic Chemistry

Volumn 72, Issue 25, 2007, Pages 9790-9793

  Hintermann, Lukas ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; SEPARATION; SOLVENTS;

IRREPRODUCIBLE ANALYSES; PEAK SEPARATION;

WATER;

SOLVENT; WATER;

ADSORPTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MEASUREMENT; SEPARATION TECHNIQUE;

EID: 36849074741     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7019256     Document Type: Article

References (39)

1. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; pp 214-295.
2. (a) HPLC Made to Measure; Kromidas, S., Ed.; Wiley-VCH: Weinheim, 2006.
3. (b) Chiral Separation Techniques, 3rd ed.; Subramanian, G., Ed.; Wiley-VCH: Weinheim, 2006.
4. (c) Chiral Separations by HPLC; Krstulovic, A. M., Ed.; Ellis Horwood Limited: Chichester, U.K., 1989.
5. (d) Unger, K. K.; Weber, E. A Guide to Practical HPLC; GIT Verlag: Darmstadt, Germany 1999.
6. High Performance Liquid Chromatography.
7. (a) Okamoto, Y.; Yashima, E. Angew. Chem., Int. Ed. 1998, 37, 1020.
8. (b) Francotte, E. R. J. Chromatogr. A 2001, 906, 379.
9. (c) Yashima, E.; Yamamoto, C.; Okamoto, Y. Synlett 1998, 344.
10. Persson, B.-A.; Andersson, S. J. Chromatogr. A 2001, 906, 195.
11. Meyer, V. R. Pitfalls and Errors of HPLC in Pictures, 2nd ed.; Wiley-VCH: Weinheim, Germany 2006.
12. Effects of water on chiral HPLC separations: (a) Balmér, K.; Persson, A.; Lagerström, P.-O.; Persson, B.-A.; Schill, G. J. Chromatogr. 1991, 553, 391.
13. (b) Balmér, K.; Lagerström, P.-O.; Persson, B.-A.; Schill, G. J. Chromatogr. 1992, 592, 331.
14. (c) Svensson, S.; Vessman, J.; Karlsson, A. J. Chromatogr. A 1999, 839, 23.
15. (d) Wang, F.; O'Brien, T.; Dowling, T.; Bicker, G.; Wyvratt, J. J. Chromatogr. A 2002, 958, 69.
16. (e) Bielejewska, A.; Duszczyk, K.; Zukowski, J. Acta Chromatogr. 2005, 15, 183.
17. (a) Snyder, L. R.; Kirkland, J. J. Introduction to Modern Liquid Chromatography; John Wiley: New York, 1979; p 374.
18. (b) Snyder, L. R. J. Chromatogr. Sci. 1969, 7, 595.
19. (a) Application Guide for Chiral Column Selection, 2nd ed.; Daicel Chemical Industries: Tokyo, 1989.
20. (b) http://www.chiral-application-guide.com/, accessed July 2007.
21. Okamoto, Y.; Kawashima, M.; Hadata, K. J. Chromatogr. 1986, 363, 173.
22. n = baseline peak with of component n. A resolution of R ≥ 1 is usually required for satisfactory peak-area ratio determinations.
23. -1, 20°C, λ = 254 nm).
24. Test-mixture: rac-1 (10.8 mg) and 2 (6.9 mg) in t-BuOMe (50 mL); injection volume = 20 μL. (14) Analyses were carried out on a Mettler KF-coulometer DL-37.
25. Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417.
26. Saito, M.; Nakajima, M.; Hashimoto, S. Chem. Commun. 2000, 1851. These authors used n-hexane as the hydrocarbon component.
27. We tend to use n-heptane in place of neurotoxic n-hexane as eluent.
28. iPrOH as eluent with trace water additions; for another example with hexane, see ref 20.
29. -1 for c/d; 20°C, λ = 254 nm).
30. Resolution enhancement in the analysis of 4 was also observed with an eluent based on hexane instead of heptane (conditions as in Figure 4): "dry", α = 1.07, R = 1.27; with 0.15% of water, α = 1.11, R = 2.18.
31. -1, 20°C, λ = 280 nm).
32. Gaffield, W.; Lundin, R., E.; Gentili, B.; Horowitz, R., M. Bioorg. Chem. 1975, 4, 259.
33. (a) Caccamese, S.; Manna, L.; Scivoli, G. Chirality 2003, 15, 661.
34. (b) Caccamese, S.; Bianca, S.; Santo, D. J. Agric. Food Chem. 2007, 55, 3816.
35. For this naringin sample: (2S/2R) = 71:29. The diastereomer ratio in commercial samples is variable; see ref 23a.
36. -1, 20°C, λ = 280 nm).
37. Structural modification of chiral stationary phases by alcohol additives: Wang, T.; Wenslow, R. M. J. Chromatogr. A 2003, 1015, 99.
38. -1, 20°C, λ = 254 nm).
39. Zhang, T.; Nguyen, D.; Franco, P.; Murakami, T.; Ohnishi, A.; Kurosawa, H. Anal. Chim. Acta 2006, 557, 221.