Chromatographic selectivity study of 4-fluorophenylacetic acid positional isomers separation

Journal of Chromatography A

Volumn 1156, Issue 1-2 SPEC. ISS., 2007, Pages 25-34

  Chasse, Tyson ^a   Wenslow, Robert ^a   Bereznitski, Yuri ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Chromatographic selectivity; Positional isomers; Solid state NMR

Indexed keywords

CHROMATOGRAPHIC SELECTIVITY; ORGANOFLUORINE COMPOUNDS; POSITIONAL ISOMERS; SOLID STATE NMR;

ACETIC ACID; CHROMATOGRAPHIC ANALYSIS; FLUORINATION; ISOMERS; NUCLEAR MAGNETIC RESONANCE; SOLVATION;

FLUORINE;

2 FLUOROPHENYLACETIC ACID; 3 FLUOROPHENYLACETIC ACID; 4 FLUOROPHENYLACETIC ACID; ACETIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; ENTHALPY; ISOMER; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SEPARATION TECHNIQUE; SOLID STATE; SOLVATION; SYNTHESIS; THERMODYNAMICS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROGEN-ION CONCENTRATION; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; PHENYLACETATES; THERMODYNAMICS;

EID: 34250643171     PISSN: 00219673     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chroma.2007.05.033     Document Type: Article

References (53)

1. Kuse M., Doi I., Kondo N., Kageyama Y., and Isobe M. Tetrahedron 61 (2005) 5754
2. Prashad M., Har D., Chen L.J., Kim H.Y., Repic O., and Blacklock T.J. J. Org. Chem. 67 (2002) 6612
3. Huang X.Y., Wang R.W., Zhao P.Q., Lu G.L., Zhang S., and Qing F.L. Polymer 46 (2005) 7590
4. Tavener S.J., and Clark J.H. J. Fluorine Chem. 123 (2003) 31
5. Fujiwara T., and Takeuchi Y. J. Fluorine Chem. 126 (2005) 941
6. Hiyama T. Organofluorine Compounds: Chemistry and Applications (2000), Springer-verlag, Berlin pp. 1
7. Filler R., and Kobayashi Y. Biomedical Aspects of Fluorine Chemistry (1982), Kodansha Ltd., Tokyo
8. R. Filler, Biochemistry involving carbon-fluorine bonds, American Chemical Society, Washington D.C.
9. In: Filler R., Kobayashi Y., and Yagupolskii L.M. (Eds). Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (1993), Elsevier, Amsterdam
10. Harper D.B., O'Hagan D., and Murphy C.D. Nat. Prod. Organohalogen Compd. 3 (2003) 141
11. Yang S.K., and Silverman B.D. Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships (1988), CRC Press, Boca Raton, FL
12. Dill J.A., Fuciarelli A.F., Lee K.M., Mellinger K.M., Chan P.C., Burka L.T., and Roycroft J.H. Toxicol. Sci. 72 (2003) 210
13. Xu L., Liu S., Wu C., and Feng Y. Electrophoresis 25 (2004) 3300
14. Chen M., and Ding W. J. Chromatogr. A 1033 (2004) 167
15. Nogami C., and Sawada H. Electrophoresis 26 (2005) 1406
16. Takeda S., Tanaka Y., Yamane M., Siroma Z., Wakida S., Otsuka K., and Terabe S. J. Chromatogr. A 924 (2001) 415
17. Andronikashvili T., Eprikashvili L., Dzagania M., and Zautashvili M. Chromatographia 50 (1999) 57
18. Xing J., Wu C., Li T., Zhong Z., and Chen Y. Anal. Sci. 15 (1999) 785
19. Yi J., and Tang K. J. Chormatgr. A 883 (2000) 137
20. Paul H., Jantunen L., Lisa M., Bidleman T., and Dorman F. J. High Resol. Chromatogr. 22 (1999) 639
21. Shao Y., and Marriott P. Anal. Bioanal. Chem. 375 (2003) 635
22. Park J., Lim H., Lee Y., and Park J. J. High Resol. Chromatogr. 22 (1999) 679
23. Schurig V., and Weber R. J. Chromatogr. 289 (1984) 321
24. T. Berger, Packard Column SFC, Royal Society of Chemistry, Cambridge, 1995.
25. Yarita T., Nomura A., Abe K., and Takeshita Y. J. Chromatogr. A 679 (1994) 329
26. Fu Q., Zheng N., Li Y., Chang W., and Wang Z. J. Mol. Recognit. 14 (2001) 151
27. Joshi V., Kulkarni M., and Mashelkar R. J. Chromatogr. A 849 (1999) 319
28. Okada Y., Okazaki Y., Koizumi K., Hara K., and Kitahata S. Carbohyd. Res. 297 (1997) 301
29. Lee Y., Ryu Y., Ryu J., Kim B., and Park J. Chromatographia 46 (1997) 507
30. Zhao J., and Carr P. Anal. Chem. 72 (2000) 302
31. Zhou L., Wu Y., Johnson B., Thompson R., and Wyvratt J. J. Chromatogr. A 866 (2000) 281
32. Shiao M., and Lin L. J. Chin. Chem. Soc-Taip 36 (1989) 429
33. Jin H., Zhang Y., Guo Y., and Jin S. Chromatographia 22 (1986) 153
34. Da S., Feng Y., Da H., Gong Y., and Zhang Y. J. Chromatogr. Sci. 37 (1999) 137
35. Xiao X., Liu X., and Jiang S. Sepu 22 (2004) 61
36. Kiridena W., DeKay C., Villiere N., Koziol W., and Poole C. Chromatographia 61 (2005) 587
37. Adlof R., and List G. J. Chromatogr. A 1046 (2004) 109
38. Xie X., and Wu C. Sepu 15 (1997) 461
39. Snyder L., and Dolan J. J. Chromatogr. A 892 (2000) 107
40. Torchia D.A. J. Magn. Res. 30 (1978) 613
41. Euerby M.R., and Patterson P. J. Chromatogr. A 994 (2003) 13
42. Snyder L.R., Kirkland J.J., and Glajch J.L. Practical HPLC Method Development (1997), Wiley, New York
43. Cheong W.J., and Carr P.W. Anal. Chem. 60 (1988) 820
44. Rutan S.C., Carr P.W., Cheong W.J., Park J.H., and Snyder L.R. J. Chromatogr. 463 (1989) 21
45. Lochmuller C.H., Hunnicutt M.L., and Mullaney J.F. J. Phys. Chem. 89 (1985) 5770
46. Dorsey J.G., and Dill K.A. Chem. Rev. 89 (1989) 331
47. ACD/PhysChem Batch for MS Windows, version 8.0, Advanced Chemistry Development, Inc. (Toronto, Canada).
48. Bayer E., Paulus A., Peters B., Laupp G., Reiners J., and Albert K. J. Chromatogr. 364 (1986) 25
49. Jaroniec M. J. Chromatogr. A 656 (1993) 37
50. Kazakevich Y.V., LoBrutto R., Chan F., and Patel T. J. Chromatogr. A 913 (2001) 75
51. Dzido T.H., Kossowski T.E., and Matosiak D. J. Chromatogr. A 947 (2002) 167
52. Ducey M.W., Orendorff C.J., and Pemberton J.E. Anal. Chem. 74 (2002) 5585
53. Pursch M., Vanderhart D.L., Sander L.C., Gu X., Nguyen T., Wise S.A., and Gajewski D. J. Am. Chem. Soc. 122 (2000) 6997