Synthesis of a novel cyclodextrin-derived chiral stationary phase with multiple urea linkages and enantioseparation toward chiral osmabenzene complex

Journal of Chromatography A

Volumn 1283, Issue , 2013, Pages 68-74

  Lin, Chun ^a   Liu, Wenna ^a   Fan, Jun ^a   Wang, Yuekui ^b   Zheng, Shengrun ^a   Lin, Ran ^c   Zhang, Hui ^c   Zhang, Weiguang ^a  

^a SOUTH CHINA NORMAL UNIVERSITY   (China)

^b SHANXI UNIVERSITY   (China)

^c XIAMEN UNIVERSITY   (China)

Author keywords

CD spectra; Chiral osmabenzene complex; Cyclodextrin based chiral stationary phase; HPLC enantioseparation; Theoretical calculation

Indexed keywords

CD SPECTRA; CHIRAL OSMABENZENE COMPLEX; CHIRAL STATIONARY PHASE; ENANTIOSEPARATIONS; THEORETICAL CALCULATIONS;

ENANTIOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SEPARATION; SILICA GEL; SURFACE REACTIONS; SYNTHESIS (CHEMICAL); UREA;

CHLORINE COMPOUNDS;

BENZENE DERIVATIVE; BETA CYCLODEXTRIN; HEPTAKIS(6 AZIDO 6 DEOXY 2,3 DI O 4 CHLOROPHENYLCARBAMOYLATED)BETA CYCLODEXTRIN; SILICA GEL; UNCLASSIFIED DRUG;

ARTICLE; CHIRAL CHROMATOGRAPHY; CHIRALITY; CIRCULAR DICHROISM; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMOBILIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PRIORITY JOURNAL; STAUDINGER REACTION; SYNTHESIS; TEMPERATURE;

BENZENE DERIVATIVES; BETA-CYCLODEXTRINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; UREA;

EID: 84875364874     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2013.01.087     Document Type: Article

References (39)

1. Ward T.J., Ward K.D. Anal. Chem. 2012, 84:626.
2. Ward T.J., Ward K.D. Anal. Chem. 2010, 82:4712.
3. Zhang Z.B., Wu M.H., Wu R.A., Dong J., Ou J.J., Zou H.F. Anal. Chem. 2011, 83:3616.
4. Lai X.H., Tang W.H., Ng S.C. J. Chromatogr. A 2011, 1218:3496.
5. Zhang Y.P., Guo Z.M., Ye J.X., Xu Q., Liang X.M., Lei A.W. J. Chromatogr. A 2008, 1191:188.
6. Li X., Zhou Z.M., Xu D., Zhang J. Talanta 2011, 84:1080.
7. Zhang Z.B., Zhang W.G., Luo W.J., Fan J. J. Chromatogr. A 2008, 1213:162.
8. Wang R.Q., Ong T.T., Ng S.C. J. Chromatogr. A 2008, 1203:185.
9. Chen L., Zhang L.F., Ching C.B., Ng S.C. J. Chromatogr. A 2002, 950:65.
10. Ng S.C., Ong T.T., Fu P., Ching C.B. J. Chromatogr. A 2002, 968:31.
11. Muderawan I.W., Ong T.T., Ng S.C. J. Sep. Sci. 2006, 29:1849.
12. Wang Y., Young D.J., Tan T.T.Y., Ng S.C. J. Chromatogr. A 2010, 1217:7878.
13. Wang Y., Ong T.T., Li L.S., Tan T.T.Y., Ng S.C. J. Chromatogr. A 2009, 1216:2388.
14. Armstrong D.W., DeMond W., Czech B.P. Anal. Chem. 1985, 57:481.
15. Snegur L.V., Boev V.I., Nekrasov Y.S., Ilyin M.M., Davankov V.A., Starikova Z.A., Yanovsky A.I., Kolomiets A.F., Babin V.N. J. Organomet. Chem. 1999, 580:26.
16. Sun P., Krishnan A., Yadav A., Singh S., MacDonnell F.M., Armstrong D.W. Inorg. Chem. 2007, 46:10312.
17. Elliott G.P., Roper W.R., Waters J.M. J. Chem. Soc. Chem. Commun. 1982, 811.
18. Bleeke J.R. Chem. Rev. 2001, 101:1205.
19. Poon K.C., Liu L., Guo T., Li J., Sung H.H.Y., Williams I.D., Lin Z., Jia G. Angew. Chem. 2010, 122:2819.
20. Lin R., Zhao J., Chen H.Y., Zhang H., Xia H.P. Chem. Asian J. 2012, 7:1915.
21. Lin R., Zhang H., Li S.H., Chen L.Q., Zhang W.G., Wen T.B., Zhang H., Xia H.P. Chem. Eur. J. 2011, 17:2420.
22. Ashton P.R., Boyd S.E., Gattuso G., Hartwell E.Y., Koniger R., Spencer N., Stoddart J.F. J. Org. Chem. 1995, 60:3898.
23. Ashton P.R., Königer R., Stoddart J.F. J. Org. Chem. 1996, 61:903.
24. Mitchel C.R., Armstrong D.W. Chiral Separations: Methods and Protocols 2004, 61. Humana Press Inc., Totowa. G. Gübitz, M.G. Schmid (Eds.).
25. Berthod A., Chang C.D., Armstrong D.W. Talanta 1993, 40:1367.
26. Qin Q., Zhang S., Zhang W.G., Zhang Z.B., Xiong Y.J., Guo Z.Y., Fan J., Zheng S.R., Finlow D., Yin Y. J. Sep. Sci. 2010, 33:2582.
27. Machida Y., Nishi H., Nakamura K. J. Chromatogr. A 1999, 830:311.
28. Hashem H., Jira T. J. Chromatogr. A 2006, 1133:69.
29. Dai J., Carr P.W. J. Chromatogr. A 2005, 1072:169.
30. Dai J., Mendonsa S.D., Bowser M.T., Lucy C.A., Carr P.W. J. Chromatogr. A 2005, 1069:225.
31. Hashem H., Tründelberg C., Attef O., Jira T. J. Chromatogr. A 2011, 1218:6727.
32. Wang Y.Z., Wu A.X. Chin. J. Org. Chem. 2008, 28:997.
33. Lin C., Luo W.J., Zhang S., Zhang W.G., Zheng S.R., Fan J., Li W.S., Qin Q., Guo Z.Y. J. Sep. Sci. 2010, 33:1558.
34. Michaud M., Jourdan E., Ravelet C., Villet A., Ravel A., Grosset C., Peyrin E. Anal. Chem. 2004, 76:1015.
35. Yao B.X., Zhan F.P., Yu G.Y., Chen Z.F., Fan W.J., Zeng X.P., Zeng Q.L., Weng W. J. Chromatogr. A 2009, 1216:5429.
36. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., Pople J.A. Gaussian 03, Revision E.01 2004, Gaussian Inc, Wallingford, CT.
37. Wang Y., Wang Y.K., Wang J.M., Liu Y., Yang Y.T. J. Am. Chem. Soc. 2009, 131:8839.
38. Su X.L., Wang Y.K., Wang Y., Jia J., Gao X.L. Acta Phys. Chim. Sin. 2011, 27:1633.
39. Wang Y.K. Application of the Time-Dependent Density Functional Theory to the Study of Chiroptical Properties of Organic and Inorganic Compounds 2003, Shaker Verlag, Aachen, p. 129.