Synthesis and Performance of Ferrocene-Bonded Chiral Stationary Phase for RP-HPLC

Hui-Jing Li; Zhi-Fang Song; Junqiang Yu; Yang Li; Ling Feng; Qi-Yong Huai

doi:10.14233/ajchem.2014.16975

Issue

Vol. 26 No. 14 (2014): Vol 26 Issue 14

Issue Published : July 5, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Performance of Ferrocene-Bonded Chiral Stationary Phase for RP-HPLC

https://doi.org/10.14233/ajchem.2014.16975

Hui-Jing Li

School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, P.R. China

Zhi-Fang Song

College of Marine Science, Shandong University (Weihai), Weihai 264209, P.R. China

Junqiang Yu

Rongcheng Entry-Exit Insepection and Quarantine Bureau, Weihai 264300, P.R. China

Yang Li

College of Marine Science, Shandong University (Weihai), Weihai 264209, P.R. China

Ling Feng

College of Marine Science, Shandong University (Weihai), Weihai 264209, P.R. China

Qi-Yong Huai

College of Marine Science, Shandong University (Weihai), Weihai 264209, P.R. China

Corresponding Author(s) : Qi-Yong Huai

huaiqy01@163.com

Asian Journal of Chemistry, Vol. 26 No. 14 (2014): Vol 26 Issue 14
Article Published : July 6, 2014

Abstract

The preparation, characterization and potential liquid chromatographic applications of a ferrocene-bonded chiral stationary phase are presented. The phase was prepared by covalent bonding of ferrocene-derivatized alanine to aminopropylated spherical silica gel. Use of the new stationary phase enabled good separations of phenylalanine, tryptophane, clenbuterol hydrochloride and thioctic acid under reversed-phase conditions within acceptable analysis times (i.e., below 20 min). The separation factors ranged between 1.07 and 1.41 and the resolutions were in no case less than 0.9. The mechanism of retention on the new stationary phase involves strong p-p interaction with each one of the cyclopentadienyl (Cp) groups of the ferrocene and simultaneously hydrogen bonding interactions between the chiral stationary phase and the analytes. The phase enables effective separation of optical isomers with a benzene ring.

Keywords

High performance liquid chromatography Ferrocene-bonded chiral stationary phase π-π Interactions

Li, H.-J., Song, Z.-F., Yu, J., Li, Y., Feng, L., & Huai, Q.-Y. (2014). Synthesis and Performance of Ferrocene-Bonded Chiral Stationary Phase for RP-HPLC. Asian Journal of Chemistry, 26(14), 4465–4468. https://doi.org/10.14233/ajchem.2014.16975

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References

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References

J. Kern and K. Kirkland, in L.R. Snyder, J.J. Kirkland, and J.L. Glajch (Eds) Practical HPLC Method Development, J. Wiley and Sons, New York, 1997, pp. 537–615.

H.Y. Aboul-Enein and I. Ali, Chiral Separations by Liquid Chromatography and Related Technologies, Marcel Dekker, New York, 2003.

(a) W.H. Pirkle and T.C. Pochapsky, Chem. Rev., 89, 347 (1989); doi:10.1021/cr00092a006.; (b) D.R. Taylor and K. Maher, J. Chromatogr. Sci., 30, 67 (1992); doi:10.1093/chromsci/30.3.67.

(a) M.H. Hyun and C.-S. Min, Bull. Korean Chem. Soc., 17, 1117 (1996); (b) M.H. Hyun, M.S. Na and C.-S. Min, J. Chromatogr. A, 732, 209 (1996); doi:10.1016/0021-9673(95)01282-6.

C.J. Welch, J. Chromatogr. A, 666, 3 (1994); doi:10.1016/0021-9673(94)80367-6.

L. Oliveros, C. Minguillón, B. Desmazières and P.-L. Desbène, J. Chromatogr. A, 589, 53 (1992); doi:10.1016/0021-9673(92)80005-F.

M.H. Hyun, Y.D. Kim, S.C. Han and J.B. Lee, J. High Resolut. Chromatogr., 21, 464 (1998); doi:10.1002/(SICI)1521-4168(19980801)21:8<464::AID-JHRC464>3.0.CO;2-#.

W.H. Pirkle, D.W. House and J.M. Finn, J. Chromatogr. A, 192, 143 (1980); doi:10.1016/S0021-9673(00)81849-X.

N. Oi, H. Kitahara, F. Aoki and N. Kisu, J. Chromatogr. A, 689, 195 (1995); doi:10.1016/0021-9673(94)00890-L.

D. Kontrec, A. Abatangelo, V. Vinkovic and V. Šunjic, Chirality, 13, 294 (2001); doi:10.1002/chir.1034.

B. Zafirova, G. Landek, D. Kontrec, V. Šunjić and V. Vinković, Croat. Chem. Acta, 77, 573 (2004).

M.H. Hyung, C.-S. Min and K.K. Jyung, Bull. Korean Chem. Soc., 17, 409 (1996).

M.H. Hyun, J.B. Lee and Y.D.J. Kim, J. High Resolut. Chromatogr., 21, 69 (1998); doi:10.1002/(SICI)1521-4168(19980101)21:1<69::AID-JHRC69>3.0.CO;2-Q.

W.H. Pirkle, D.W. House and J.M. Finn, J. Chromatogr. A, 192, 143 (1980); doi:10.1016/S0021-9673(00)81849-X.

E. Badaloni, W. Cabri, A. Ciogli, R. Deias, F. Gasparrini, F. Giorgi, A. Vigevani and C. Villani, Anal. Chem., 79, 6013 (2007); doi:10.1021/ac070776j.

W.H. Pirkle and W. Lee, Bull. Korean Chem. Soc., 31, 620 (2010); doi:10.5012/bkcs.2010.31.03.620.

G. Cancelliere, A. Ciogli, I. D’Acquarica, F. Gasparrini, J. Kocergin, D. Misiti, M. Pierini, H. Ritchie, P. Simone and C. Villani, J. Chromatogr. A, 1217, 990 (2010); doi:10.1016/j.chroma.2009.10.021.

M.D. Slater, J.M.J. Frechet and F. Svec, J. Sep. Sci., 32, 21 (2009); doi:10.1002/jssc.200800493.

W.J. Wei, H.W. Deng, W. Chen, Z.W. Bai and S.R. Li, Chirality, 22, 604 (2010); doi:10.1002/chir.20799.

H.J. Choi, H.J. Ha, M.S. Shin, J.S. Jin, M.H. Hyun, J. Liq. Chromatogr. Relat. Technol., 32, 1879 (2009); doi: 10.1080/10826070903091589.

K. Ohyama, K. Oyamada, N. Kishikawa, M. Arakawa, Y. Ohba, M. Kamino, M. Wada, K. Nakashima and N. Kuroda, Chromatographia, 70, 1501 (2009); doi:10.1365/s10337-009-1345-z.

Issue

Vol. 26 No. 14 (2014): Vol 26 Issue 14

Synthesis and Performance of Ferrocene-Bonded Chiral Stationary Phase for RP-HPLC

Corresponding Author(s) : Qi-Yong Huai

Abstract

Keywords

Full Article

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