Enantioselective binding in gas chromatography: A computational study of chiral selection by permethyl-β-cyclodextrin

Journal of Physical Organic Chemistry

Volumn 10, Issue 5, 1997, Pages 311-322

  Lipkowitz, Kenny B ^a   Coner, Bob ^a   Peterson, Michael A ^a   Morreale, Antonio ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Chiral selection; Enantioselective binding; Gas chromatography; Permethyl cyclodextrin

Indexed keywords

EID: 0000087554     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1395(199705)10:5<311::AID-POC871>3.0.CO;2-P     Document Type: Article

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16. For reviews, see (a) T. J. Ward and D. W. Armstrong, J. Liq. Chromatogr. 9, 407-411 (1986); (b) J. Martens and R. Bhushan, Chem. Ztg. 112, 367-371 (1988); (c) J. Martens and R. Bhushan, Int. J. Pep. Protein Res. 34, 433-439 (1989); (d) J. Martens and R. Bhushan, J. Pharm. Biomed. Anal. 8, 259-265 (1990); (e) R. Bhushan and S. Joshi, Biomed. Chromatogr. 7, 235-241 (1993).
17. For reviews, see (a) T. J. Ward and D. W. Armstrong, J. Liq. Chromatogr. 9, 407-411 (1986); (b) J. Martens and R. Bhushan, Chem. Ztg. 112, 367-371 (1988); (c) J. Martens and R. Bhushan, Int. J. Pep. Protein Res. 34, 433-439 (1989); (d) J. Martens and R. Bhushan, J. Pharm. Biomed. Anal. 8, 259-265 (1990); (e) R. Bhushan and S. Joshi, Biomed. Chromatogr. 7, 235-241 (1993).
18. Pertinent discussions can be found in Ref. 1; for additional reviews concerning gas chromatocraphic applications of cyclodextrins, see (a) W. A. König, in Drug Stereochemistry, Analytical Methods and Pharmacology, edited by I. W. Wainer, and D. E. Drayer, pp. 113-145. Marcel Dekker, New York (1988). (b) V. Schurig and H.-P. Nowotny, Angew. Chem., Int. Ed. Engl. 29, 939-942 (1990); (c) M. Jung, S. Mayer and V. Schurig, LC·GC 458-462 (1994); (d) V. Mani and C. Wooley, LC·GC 734-737 (1995).
19. Pertinent discussions can be found in Ref. 1; for additional reviews concerning gas chromatocraphic applications of cyclodextrins, see (a) W. A. König, in Drug Stereochemistry, Analytical Methods and Pharmacology, edited by I. W. Wainer, and D. E. Drayer, pp. 113-145. Marcel Dekker, New York (1988). (b) V. Schurig and H.-P. Nowotny, Angew. Chem., Int. Ed. Engl. 29, 939-942 (1990); (c) M. Jung, S. Mayer and V. Schurig, LC·GC 458-462 (1994); (d) V. Mani and C. Wooley, LC·GC 734-737 (1995).
20. Pertinent discussions can be found in Ref. 1; for additional reviews concerning gas chromatocraphic applications of cyclodextrins, see (a) W. A. König, in Drug Stereochemistry, Analytical Methods and Pharmacology, edited by I. W. Wainer, and D. E. Drayer, pp. 113-145. Marcel Dekker, New York (1988). (b) V. Schurig and H.-P. Nowotny, Angew. Chem., Int. Ed. Engl. 29, 939-942 (1990); (c) M. Jung, S. Mayer and V. Schurig, LC·GC 458-462 (1994); (d) V. Mani and C. Wooley, LC·GC 734-737 (1995).
21. Pertinent discussions can be found in Ref. 1; for additional reviews concerning gas chromatocraphic applications of cyclodextrins, see (a) W. A. König, in Drug Stereochemistry, Analytical Methods and Pharmacology, edited by I. W. Wainer, and D. E. Drayer, pp. 113-145. Marcel Dekker, New York (1988). (b) V. Schurig and H.-P. Nowotny, Angew. Chem., Int. Ed. Engl. 29, 939-942 (1990); (c) M. Jung, S. Mayer and V. Schurig, LC·GC 458-462 (1994); (d) V. Mani and C. Wooley, LC·GC 734-737 (1995).
22. Pertinent discussions can be found throughout Ref. 1; for additional reviews concerning applications of cyclodextrins in liquid Chromatography, see (a) D. W. Armstrong, A. Alak, K. Bui, W. DeMond, T. Ward, T. E. Riehl and W. L. Hinze, J. Inclu. Phenom. 2, 533-538 (1984); (b) D. W. Armstrong, J. Liq. Chromatogr. 7, 353-360 (1984); (c) T. E. Beesley, Am. Lab. May, 78-81 (1985); (d) T. J. Ward and D. W. Armstrong, J. Liq. Chromatogr. 9, 407-411 (1986); (e) D. W. Armstrong and S. Han, CRC Critical Rev. Anal. Chem. 19, 175-189 (1988); (f) D. Johns, Am. Lab. January, 72-77 (1987); (g) D. W. Armstrong, Anal. Chem. 59, 84-90 (1987); (h) C. Pettersson, Trends Anal. Chem. 7, 209-213 (1988); (i) D. W. Armstrong, M. Hilton and L. Coffin, LC·GC. 646-651 (1991); (j) N. Husain and I. M. Warner, Am. Lab. October, 80-85 (1993).
23. Pertinent discussions can be found throughout Ref. 1; for additional reviews concerning applications of cyclodextrins in liquid Chromatography, see (a) D. W. Armstrong, A. Alak, K. Bui, W. DeMond, T. Ward, T. E. Riehl and W. L. Hinze, J. Inclu. Phenom. 2, 533-538 (1984); (b) D. W. Armstrong, J. Liq. Chromatogr. 7, 353-360 (1984); (c) T. E. Beesley, Am. Lab. May, 78-81 (1985); (d) T. J. Ward and D. W. Armstrong, J. Liq. Chromatogr. 9, 407-411 (1986); (e) D. W. Armstrong and S. Han, CRC Critical Rev. Anal. Chem. 19, 175-189 (1988); (f) D. Johns, Am. Lab. January, 72-77 (1987); (g) D. W. Armstrong, Anal. Chem. 59, 84-90 (1987); (h) C. Pettersson, Trends Anal. Chem. 7, 209-213 (1988); (i) D. W. Armstrong, M. Hilton and L. Coffin, LC·GC. 646-651 (1991); (j) N. Husain and I. M. Warner, Am. Lab. October, 80-85 (1993).
24. Pertinent discussions can be found throughout Ref. 1; for additional reviews concerning applications of cyclodextrins in liquid Chromatography, see (a) D. W. Armstrong, A. Alak, K. Bui, W. DeMond, T. Ward, T. E. Riehl and W. L. Hinze, J. Inclu. Phenom. 2, 533-538 (1984); (b) D. W. Armstrong, J. Liq. Chromatogr. 7, 353-360 (1984); (c) T. E. Beesley, Am. Lab. May, 78-81 (1985); (d) T. J. Ward and D. W. Armstrong, J. Liq. Chromatogr. 9, 407-411 (1986); (e) D. W. Armstrong and S. Han, CRC Critical Rev. Anal. Chem. 19, 175-189 (1988); (f) D. Johns, Am. Lab. January, 72-77 (1987); (g) D. W. Armstrong, Anal. Chem. 59, 84-90 (1987); (h) C. Pettersson, Trends Anal. Chem. 7, 209-213 (1988); (i) D. W. Armstrong, M. Hilton and L. Coffin, LC·GC. 646-651 (1991); (j) N. Husain and I. M. Warner, Am. Lab. October, 80-85 (1993).
25. Pertinent discussions can be found throughout Ref. 1; for additional reviews concerning applications of cyclodextrins in liquid Chromatography, see (a) D. W. Armstrong, A. Alak, K. Bui, W. DeMond, T. Ward, T. E. Riehl and W. L. Hinze, J. Inclu. Phenom. 2, 533-538 (1984); (b) D. W. Armstrong, J. Liq. Chromatogr. 7, 353-360 (1984); (c) T. E. Beesley, Am. Lab. May, 78-81 (1985); (d) T. J. Ward and D. W. Armstrong, J. Liq. Chromatogr. 9, 407-411 (1986); (e) D. W. Armstrong and S. Han, CRC Critical Rev. Anal. Chem. 19, 175-189 (1988); (f) D. Johns, Am. Lab. January, 72-77 (1987); (g) D. W. Armstrong, Anal. Chem. 59, 84-90 (1987); (h) C. Pettersson, Trends Anal. Chem. 7, 209-213 (1988); (i) D. W. Armstrong, M. Hilton and L. Coffin, LC·GC. 646-651 (1991); (j) N. Husain and I. M. Warner, Am. Lab. October, 80-85 (1993).
26. Pertinent discussions can be found throughout Ref. 1; for additional reviews concerning applications of cyclodextrins in liquid Chromatography, see (a) D. W. Armstrong, A. Alak, K. Bui, W. DeMond, T. Ward, T. E. Riehl and W. L. Hinze, J. Inclu. Phenom. 2, 533-538 (1984); (b) D. W. Armstrong, J. Liq. Chromatogr. 7, 353-360 (1984); (c) T. E. Beesley, Am. Lab. May, 78-81 (1985); (d) T. J. Ward and D. W. Armstrong, J. Liq. Chromatogr. 9, 407-411 (1986); (e) D. W. Armstrong and S. Han, CRC Critical Rev. Anal. Chem. 19, 175-189 (1988); (f) D. Johns, Am. Lab. January, 72-77 (1987); (g) D. W. Armstrong, Anal. Chem. 59, 84-90 (1987); (h) C. Pettersson, Trends Anal. Chem. 7, 209-213 (1988); (i) D. W. Armstrong, M. Hilton and L. Coffin, LC·GC. 646-651 (1991); (j) N. Husain and I. M. Warner, Am. Lab. October, 80-85 (1993).
27. Pertinent discussions can be found throughout Ref. 1; for additional reviews concerning applications of cyclodextrins in liquid Chromatography, see (a) D. W. Armstrong, A. Alak, K. Bui, W. DeMond, T. Ward, T. E. Riehl and W. L. Hinze, J. Inclu. Phenom. 2, 533-538 (1984); (b) D. W. Armstrong, J. Liq. Chromatogr. 7, 353-360 (1984); (c) T. E. Beesley, Am. Lab. May, 78-81 (1985); (d) T. J. Ward and D. W. Armstrong, J. Liq. Chromatogr. 9, 407-411 (1986); (e) D. W. Armstrong and S. Han, CRC Critical Rev. Anal. Chem. 19, 175-189 (1988); (f) D. Johns, Am. Lab. January, 72-77 (1987); (g) D. W. Armstrong, Anal. Chem. 59, 84-90 (1987); (h) C. Pettersson, Trends Anal. Chem. 7, 209-213 (1988); (i) D. W. Armstrong, M. Hilton and L. Coffin, LC·GC. 646-651 (1991); (j) N. Husain and I. M. Warner, Am. Lab. October, 80-85 (1993).
28. Pertinent discussions can be found throughout Ref. 1; for additional reviews concerning applications of cyclodextrins in liquid Chromatography, see (a) D. W. Armstrong, A. Alak, K. Bui, W. DeMond, T. Ward, T. E. Riehl and W. L. Hinze, J. Inclu. Phenom. 2, 533-538 (1984); (b) D. W. Armstrong, J. Liq. Chromatogr. 7, 353-360 (1984); (c) T. E. Beesley, Am. Lab. May, 78-81 (1985); (d) T. J. Ward and D. W. Armstrong, J. Liq. Chromatogr. 9, 407-411 (1986); (e) D. W. Armstrong and S. Han, CRC Critical Rev. Anal. Chem. 19, 175-189 (1988); (f) D. Johns, Am. Lab. January, 72-77 (1987); (g) D. W. Armstrong, Anal. Chem. 59, 84-90 (1987); (h) C. Pettersson, Trends Anal. Chem. 7, 209-213 (1988); (i) D. W. Armstrong, M. Hilton and L. Coffin, LC·GC. 646-651 (1991); (j) N. Husain and I. M. Warner, Am. Lab. October, 80-85 (1993).
29. Pertinent discussions can be found throughout Ref. 1; for additional reviews concerning applications of cyclodextrins in liquid Chromatography, see (a) D. W. Armstrong, A. Alak, K. Bui, W. DeMond, T. Ward, T. E. Riehl and W. L. Hinze, J. Inclu. Phenom. 2, 533-538 (1984); (b) D. W. Armstrong, J. Liq. Chromatogr. 7, 353-360 (1984); (c) T. E. Beesley, Am. Lab. May, 78-81 (1985); (d) T. J. Ward and D. W. Armstrong, J. Liq. Chromatogr. 9, 407-411 (1986); (e) D. W. Armstrong and S. Han, CRC Critical Rev. Anal. Chem. 19, 175-189 (1988); (f) D. Johns, Am. Lab. January, 72-77 (1987); (g) D. W. Armstrong, Anal. Chem. 59, 84-90 (1987); (h) C. Pettersson, Trends Anal. Chem. 7, 209-213 (1988); (i) D. W. Armstrong, M. Hilton and L. Coffin, LC·GC. 646-651 (1991); (j) N. Husain and I. M. Warner, Am. Lab. October, 80-85 (1993).
30. Pertinent discussions can be found throughout Ref. 1; for additional reviews concerning applications of cyclodextrins in liquid Chromatography, see (a) D. W. Armstrong, A. Alak, K. Bui, W. DeMond, T. Ward, T. E. Riehl and W. L. Hinze, J. Inclu. Phenom. 2, 533-538 (1984); (b) D. W. Armstrong, J. Liq. Chromatogr. 7, 353-360 (1984); (c) T. E. Beesley, Am. Lab. May, 78-81 (1985); (d) T. J. Ward and D. W. Armstrong, J. Liq. Chromatogr. 9, 407-411 (1986); (e) D. W. Armstrong and S. Han, CRC Critical Rev. Anal. Chem. 19, 175-189 (1988); (f) D. Johns, Am. Lab. January, 72-77 (1987); (g) D. W. Armstrong, Anal. Chem. 59, 84-90 (1987); (h) C. Pettersson, Trends Anal. Chem. 7, 209-213 (1988); (i) D. W. Armstrong, M. Hilton and L. Coffin, LC·GC. 646-651 (1991); (j) N. Husain and I. M. Warner, Am. Lab. October, 80-85 (1993).
31. Pertinent discussions can be found throughout Ref. 1; for additional reviews concerning applications of cyclodextrins in liquid Chromatography, see (a) D. W. Armstrong, A. Alak, K. Bui, W. DeMond, T. Ward, T. E. Riehl and W. L. Hinze, J. Inclu. Phenom. 2, 533-538 (1984); (b) D. W. Armstrong, J. Liq. Chromatogr. 7, 353-360 (1984); (c) T. E. Beesley, Am. Lab. May, 78-81 (1985); (d) T. J. Ward and D. W. Armstrong, J. Liq. Chromatogr. 9, 407-411 (1986); (e) D. W. Armstrong and S. Han, CRC Critical Rev. Anal. Chem. 19, 175-189 (1988); (f) D. Johns, Am. Lab. January, 72-77 (1987); (g) D. W. Armstrong, Anal. Chem. 59, 84-90 (1987); (h) C. Pettersson, Trends Anal. Chem. 7, 209-213 (1988); (i) D. W. Armstrong, M. Hilton and L. Coffin, LC·GC. 646-651 (1991); (j) N. Husain and I. M. Warner, Am. Lab. October, 80-85 (1993).
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59. W. F. van Gunsteren and H. J. C. Berendsen, Mol. Simul. 1, 173-184 (1988).
60. Several groups have carried out limonene resolutions on this CSP, including (a) V. Schurig and H.-P. Nowotny, J. Chromalogr. 441, 155-163 (1988), (b) V. Schurig, M. Jung, D. Schmalzing, M. Schleimer, J. Duvekot, J. C. Buyten, J. A. Peene and P. Mussche, J. High Resolut. Chromatogr. 13, 470-474 (1990); (c) G. Takeoka, R. A. Flath, T. R. Mon, R. G. Buttery, R. Teranishi, M. Güntert, R. Lautamo and J. Szejtli, J. High Resolut. Chromatogr. 13, 202-206 (1990); (d) C. Askari, U. Hener, H.-G. Schmarr, A. Rapp and A. Mosandl., Fresenius J. Anal. Chem. 340, 768-772 (1991); (e) W. Keim, A. Köhnes, W. Meltzow and H. Römer, J. High Resolut. Chromatogr. 14, 507-529 (1991); (f) A. Mosandl, K. Fischer, U. Hener, P. Kreis, K. Rettinger, V. Schubert and H.-G. Schmarr, J. Agric. Food Chem. 39, 1131-1134 (1991); (g) C. Bicchi, G. Artuffo, A. D'Amato, A. Galli and M. Galli, Chirality 4, 125-131 (1992); (h) F. Kobor, K. Angermund and G. Schomburg, J. High Resolut. Chmmatogr. 16, 299-311 (1993).
61. Several groups have carried out limonene resolutions on this CSP, including (a) V. Schurig and H.-P. Nowotny, J. Chromalogr. 441, 155-163 (1988), (b) V. Schurig, M. Jung, D. Schmalzing, M. Schleimer, J. Duvekot, J. C. Buyten, J. A. Peene and P. Mussche, J. High Resolut. Chromatogr. 13, 470-474 (1990); (c) G. Takeoka, R. A. Flath, T. R. Mon, R. G. Buttery, R. Teranishi, M. Güntert, R. Lautamo and J. Szejtli, J. High Resolut. Chromatogr. 13, 202-206 (1990); (d) C. Askari, U. Hener, H.-G. Schmarr, A. Rapp and A. Mosandl., Fresenius J. Anal. Chem. 340, 768-772 (1991); (e) W. Keim, A. Köhnes, W. Meltzow and H. Römer, J. High Resolut. Chromatogr. 14, 507-529 (1991); (f) A. Mosandl, K. Fischer, U. Hener, P. Kreis, K. Rettinger, V. Schubert and H.-G. Schmarr, J. Agric. Food Chem. 39, 1131-1134 (1991); (g) C. Bicchi, G. Artuffo, A. D'Amato, A. Galli and M. Galli, Chirality 4, 125-131 (1992); (h) F. Kobor, K. Angermund and G. Schomburg, J. High Resolut. Chmmatogr. 16, 299-311 (1993).
62. Several groups have carried out limonene resolutions on this CSP, including (a) V. Schurig and H.-P. Nowotny, J. Chromalogr. 441, 155-163 (1988), (b) V. Schurig, M. Jung, D. Schmalzing, M. Schleimer, J. Duvekot, J. C. Buyten, J. A. Peene and P. Mussche, J. High Resolut. Chromatogr. 13, 470-474 (1990); (c) G. Takeoka, R. A. Flath, T. R. Mon, R. G. Buttery, R. Teranishi, M. Güntert, R. Lautamo and J. Szejtli, J. High Resolut. Chromatogr. 13, 202-206 (1990); (d) C. Askari, U. Hener, H.-G. Schmarr, A. Rapp and A. Mosandl., Fresenius J. Anal. Chem. 340, 768-772 (1991); (e) W. Keim, A. Köhnes, W. Meltzow and H. Römer, J. High Resolut. Chromatogr. 14, 507-529 (1991); (f) A. Mosandl, K. Fischer, U. Hener, P. Kreis, K. Rettinger, V. Schubert and H.-G. Schmarr, J. Agric. Food Chem. 39, 1131-1134 (1991); (g) C. Bicchi, G. Artuffo, A. D'Amato, A. Galli and M. Galli, Chirality 4, 125-131 (1992); (h) F. Kobor, K. Angermund and G. Schomburg, J. High Resolut. Chmmatogr. 16, 299-311 (1993).
63. Several groups have carried out limonene resolutions on this CSP, including (a) V. Schurig and H.-P. Nowotny, J. Chromalogr. 441, 155-163 (1988), (b) V. Schurig, M. Jung, D. Schmalzing, M. Schleimer, J. Duvekot, J. C. Buyten, J. A. Peene and P. Mussche, J. High Resolut. Chromatogr. 13, 470-474 (1990); (c) G. Takeoka, R. A. Flath, T. R. Mon, R. G. Buttery, R. Teranishi, M. Güntert, R. Lautamo and J. Szejtli, J. High Resolut. Chromatogr. 13, 202-206 (1990); (d) C. Askari, U. Hener, H.-G. Schmarr, A. Rapp and A. Mosandl., Fresenius J. Anal. Chem. 340, 768-772 (1991); (e) W. Keim, A. Köhnes, W. Meltzow and H. Römer, J. High Resolut. Chromatogr. 14, 507-529 (1991); (f) A. Mosandl, K. Fischer, U. Hener, P. Kreis, K. Rettinger, V. Schubert and H.-G. Schmarr, J. Agric. Food Chem. 39, 1131-1134 (1991); (g) C. Bicchi, G. Artuffo, A. D'Amato, A. Galli and M. Galli, Chirality 4, 125-131 (1992); (h) F. Kobor, K. Angermund and G. Schomburg, J. High Resolut. Chmmatogr. 16, 299-311 (1993).
64. Several groups have carried out limonene resolutions on this CSP, including (a) V. Schurig and H.-P. Nowotny, J. Chromalogr. 441, 155-163 (1988), (b) V. Schurig, M. Jung, D. Schmalzing, M. Schleimer, J. Duvekot, J. C. Buyten, J. A. Peene and P. Mussche, J. High Resolut. Chromatogr. 13, 470-474 (1990); (c) G. Takeoka, R. A. Flath, T. R. Mon, R. G. Buttery, R. Teranishi, M. Güntert, R. Lautamo and J. Szejtli, J. High Resolut. Chromatogr. 13, 202-206 (1990); (d) C. Askari, U. Hener, H.-G. Schmarr, A. Rapp and A. Mosandl., Fresenius J. Anal. Chem. 340, 768-772 (1991); (e) W. Keim, A. Köhnes, W. Meltzow and H. Römer, J. High Resolut. Chromatogr. 14, 507-529 (1991); (f) A. Mosandl, K. Fischer, U. Hener, P. Kreis, K. Rettinger, V. Schubert and H.-G. Schmarr, J. Agric. Food Chem. 39, 1131-1134 (1991); (g) C. Bicchi, G. Artuffo, A. D'Amato, A. Galli and M. Galli, Chirality 4, 125-131 (1992); (h) F. Kobor, K. Angermund and G. Schomburg, J. High Resolut. Chmmatogr. 16, 299-311 (1993).
65. Several groups have carried out limonene resolutions on this CSP, including (a) V. Schurig and H.-P. Nowotny, J. Chromalogr. 441, 155-163 (1988), (b) V. Schurig, M. Jung, D. Schmalzing, M. Schleimer, J. Duvekot, J. C. Buyten, J. A. Peene and P. Mussche, J. High Resolut. Chromatogr. 13, 470-474 (1990); (c) G. Takeoka, R. A. Flath, T. R. Mon, R. G. Buttery, R. Teranishi, M. Güntert, R. Lautamo and J. Szejtli, J. High Resolut. Chromatogr. 13, 202-206 (1990); (d) C. Askari, U. Hener, H.-G. Schmarr, A. Rapp and A. Mosandl., Fresenius J. Anal. Chem. 340, 768-772 (1991); (e) W. Keim, A. Köhnes, W. Meltzow and H. Römer, J. High Resolut. Chromatogr. 14, 507-529 (1991); (f) A. Mosandl, K. Fischer, U. Hener, P. Kreis, K. Rettinger, V. Schubert and H.-G. Schmarr, J. Agric. Food Chem. 39, 1131-1134 (1991); (g) C. Bicchi, G. Artuffo, A. D'Amato, A. Galli and M. Galli, Chirality 4, 125-131 (1992); (h) F. Kobor, K. Angermund and G. Schomburg, J. High Resolut. Chmmatogr. 16, 299-311 (1993).
66. Several groups have carried out limonene resolutions on this CSP, including (a) V. Schurig and H.-P. Nowotny, J. Chromalogr. 441, 155-163 (1988), (b) V. Schurig, M. Jung, D. Schmalzing, M. Schleimer, J. Duvekot, J. C. Buyten, J. A. Peene and P. Mussche, J. High Resolut. Chromatogr. 13, 470-474 (1990); (c) G. Takeoka, R. A. Flath, T. R. Mon, R. G. Buttery, R. Teranishi, M. Güntert, R. Lautamo and J. Szejtli, J. High Resolut. Chromatogr. 13, 202-206 (1990); (d) C. Askari, U. Hener, H.-G. Schmarr, A. Rapp and A. Mosandl., Fresenius J. Anal. Chem. 340, 768-772 (1991); (e) W. Keim, A. Köhnes, W. Meltzow and H. Römer, J. High Resolut. Chromatogr. 14, 507-529 (1991); (f) A. Mosandl, K. Fischer, U. Hener, P. Kreis, K. Rettinger, V. Schubert and H.-G. Schmarr, J. Agric. Food Chem. 39, 1131-1134 (1991); (g) C. Bicchi, G. Artuffo, A. D'Amato, A. Galli and M. Galli, Chirality 4, 125-131 (1992); (h) F. Kobor, K. Angermund and G. Schomburg, J. High Resolut. Chmmatogr. 16, 299-311 (1993).
67. Several groups have carried out limonene resolutions on this CSP, including (a) V. Schurig and H.-P. Nowotny, J. Chromalogr. 441, 155-163 (1988), (b) V. Schurig, M. Jung, D. Schmalzing, M. Schleimer, J. Duvekot, J. C. Buyten, J. A. Peene and P. Mussche, J. High Resolut. Chromatogr. 13, 470-474 (1990); (c) G. Takeoka, R. A. Flath, T. R. Mon, R. G. Buttery, R. Teranishi, M. Güntert, R. Lautamo and J. Szejtli, J. High Resolut. Chromatogr. 13, 202-206 (1990); (d) C. Askari, U. Hener, H.-G. Schmarr, A. Rapp and A. Mosandl., Fresenius J. Anal. Chem. 340, 768-772 (1991); (e) W. Keim, A. Köhnes, W. Meltzow and H. Römer, J. High Resolut. Chromatogr. 14, 507-529 (1991); (f) A. Mosandl, K. Fischer, U. Hener, P. Kreis, K. Rettinger, V. Schubert and H.-G. Schmarr, J. Agric. Food Chem. 39, 1131-1134 (1991); (g) C. Bicchi, G. Artuffo, A. D'Amato, A. Galli and M. Galli, Chirality 4, 125-131 (1992); (h) F. Kobor, K. Angermund and G. Schomburg, J. High Resolut. Chmmatogr. 16, 299-311 (1993).
68. Several groups have resolved pinene on this CSP including all the citations in Ref. 19 and R. Reinhardt, A. Steinborn, W. Engewald, K. Anhalt and K. Schulze, J. Chromatogr. A 697, 475-484 (1995).
69. R. Reinhardt, W. Engewald, O. Goj and G. Haufe, Chromatographia 39, 192-199 (1994).
70. K. B. Lipkowitz, J. Org. Chem. 56, 6357-6357 (1991).
71. For leading references, see (a) J. Wang and I. M. Warner Microchem. J. 229 (1993); (b) A. Botsi, K. Yannakopoulou, B. Perly and E. Hadjoudis, J. Org. Chem. 60, 4017 (1995); (c) J. Redondo, J. Frigola, A. Torrens and P. Lupón, Magn. Reson. Chem. 33, 104 (1995).
72. For leading references, see (a) J. Wang and I. M. Warner Microchem. J. 229 (1993); (b) A. Botsi, K. Yannakopoulou, B. Perly and E. Hadjoudis, J. Org. Chem. 60, 4017 (1995); (c) J. Redondo, J. Frigola, A. Torrens and P. Lupón, Magn. Reson. Chem. 33, 104 (1995).
73. For leading references, see (a) J. Wang and I. M. Warner Microchem. J. 229 (1993); (b) A. Botsi, K. Yannakopoulou, B. Perly and E. Hadjoudis, J. Org. Chem. 60, 4017 (1995); (c) J. Redondo, J. Frigola, A. Torrens and P. Lupón, Magn. Reson. Chem. 33, 104 (1995).