Abstract
Normal phase chiral HPLC and SFC methods are presented for the enantiomeric separation of 21 α-aryl ketones with a unique class of chiral stationary phases (CSPs) based on cyclofructans (CFs). Separations were achieved for all but 2 analytes, with 17 compounds attaining baseline separation having resolution values up to 4.0. Most separations obtained in HPLC could be transferred to SFC, but the HPLC resolutions were generally better due to greater enantiomeric selectivity values. A structure-separation relationship (SSR) was developed to identify important structural features for separation of this class of compounds using CF-based CSPs. Preliminary studies are also presented that demonstrate the utility of the CF CSPs to investigate the base-induced enantiomerization of α-aryl ketones. It was demonstrated that even small amounts of base (0.01%. v/v) in the mobile phase results in rapid, on-column, enantiomerization. Lastly, CSPs composed of superficially porous particles were used to achieve comparable separations of this class of chiral compounds, but at a fraction of the analysis time compared to CSPs composed of fully porous particles.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 45-54 |
| Number of pages | 10 |
| Journal | Journal of Chromatography A |
| Volume | 1427 |
| DOIs | |
| State | Published - Jan 4 2016 |
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Keywords
- Cyclofructan chiral stationary phase
- Enantiomerization
- HPLC and SFC enantiomeric separation
- Structure-separation relationship (SSR)
- Superficially porous particle
- α-Aryl ketone
ASJC Scopus subject areas
- Analytical Chemistry
- Organic Chemistry
- Biochemistry
Cite this
Enantiomeric separations of α-aryl ketones with cyclofructan chiral stationary phases via high performance liquid chromatography and supercritical fluid chromatography. / Breitbach, Anthony S.; Lim, Yeeun; Xu, Qing Long; Kürti, László; Armstrong, Daniel W.; Breitbach, Zachary S.
In: Journal of Chromatography A, Vol. 1427, 04.01.2016, p. 45-54.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Enantiomeric separations of α-aryl ketones with cyclofructan chiral stationary phases via high performance liquid chromatography and supercritical fluid chromatography
AU - Breitbach, Anthony S.
AU - Lim, Yeeun
AU - Xu, Qing Long
AU - Kürti, László
AU - Armstrong, Daniel W.
AU - Breitbach, Zachary S.
PY - 2016/1/4
Y1 - 2016/1/4
N2 - Normal phase chiral HPLC and SFC methods are presented for the enantiomeric separation of 21 α-aryl ketones with a unique class of chiral stationary phases (CSPs) based on cyclofructans (CFs). Separations were achieved for all but 2 analytes, with 17 compounds attaining baseline separation having resolution values up to 4.0. Most separations obtained in HPLC could be transferred to SFC, but the HPLC resolutions were generally better due to greater enantiomeric selectivity values. A structure-separation relationship (SSR) was developed to identify important structural features for separation of this class of compounds using CF-based CSPs. Preliminary studies are also presented that demonstrate the utility of the CF CSPs to investigate the base-induced enantiomerization of α-aryl ketones. It was demonstrated that even small amounts of base (0.01%. v/v) in the mobile phase results in rapid, on-column, enantiomerization. Lastly, CSPs composed of superficially porous particles were used to achieve comparable separations of this class of chiral compounds, but at a fraction of the analysis time compared to CSPs composed of fully porous particles.
AB - Normal phase chiral HPLC and SFC methods are presented for the enantiomeric separation of 21 α-aryl ketones with a unique class of chiral stationary phases (CSPs) based on cyclofructans (CFs). Separations were achieved for all but 2 analytes, with 17 compounds attaining baseline separation having resolution values up to 4.0. Most separations obtained in HPLC could be transferred to SFC, but the HPLC resolutions were generally better due to greater enantiomeric selectivity values. A structure-separation relationship (SSR) was developed to identify important structural features for separation of this class of compounds using CF-based CSPs. Preliminary studies are also presented that demonstrate the utility of the CF CSPs to investigate the base-induced enantiomerization of α-aryl ketones. It was demonstrated that even small amounts of base (0.01%. v/v) in the mobile phase results in rapid, on-column, enantiomerization. Lastly, CSPs composed of superficially porous particles were used to achieve comparable separations of this class of chiral compounds, but at a fraction of the analysis time compared to CSPs composed of fully porous particles.
KW - Cyclofructan chiral stationary phase
KW - Enantiomerization
KW - HPLC and SFC enantiomeric separation
KW - Structure-separation relationship (SSR)
KW - Superficially porous particle
KW - α-Aryl ketone
UR - http://www.scopus.com/inward/record.url?scp=84955408692&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84955408692&partnerID=8YFLogxK
U2 - 10.1016/j.chroma.2015.11.069
DO - 10.1016/j.chroma.2015.11.069
M3 - Article
C2 - 26687164
AN - SCOPUS:84955408692
VL - 1427
SP - 45
EP - 54
JO - Journal of Chromatography
JF - Journal of Chromatography
SN - 0021-9673
ER -