Chromatography 2014, 1(2), 65-74; doi:10.3390/chromatography1020065
Article

Influence of the Azulene Ring on the Enantioseparation of 1,5-Diols

Received: 3 April 2014; in revised form: 9 May 2014 / Accepted: 12 May 2014 / Published: 16 May 2014
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The enantioseparation of a series of six azulene-centered 1,5-diol enantiomers was studied employing two cellulose-based chiral stationary phases under normal phase conditions (isopropanol/hexanes). The separations were generally quite good on Chiralcel-OD-H, with α values ranging from 1.2 to 8.4 (average 4.0) and resolution values of 0.4–8.3 (average 4.7). Only one of the six enantiomer pairs was not well resolved, but was well separated on Lux cellulose 2 (α 1.4, Rs 8.7). It was observed that the enantioseparations of the RS/SR diastereomers (ave α = 7.8, Rs = 8.2) were dramatically better than that of the corresponding RR/SS diastereomers (ave α = 2.1, Rs = 3.0) on Chiralcel-OD-H. The better-resolved diastereomer pairs correspond to the more strongly retained diastereomers on silica gel. The enantiomers of two benzene 1,5-diols were much more poorly separated on both stationary phases, suggesting that the unusual polarity of the azulene ring enhances critical interactions with these phases.
Keywords: chiral azulene; chiral high-pressure liquid chromatography; enantioseparation
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MDPI and ACS Style

Horgen, D.A.; Garner, C.M. Influence of the Azulene Ring on the Enantioseparation of 1,5-Diols. Chromatography 2014, 1, 65-74.

AMA Style

Horgen DA, Garner CM. Influence of the Azulene Ring on the Enantioseparation of 1,5-Diols. Chromatography. 2014; 1(2):65-74.

Chicago/Turabian Style

Horgen, Dana A.; Garner, Charles M. 2014. "Influence of the Azulene Ring on the Enantioseparation of 1,5-Diols." Chromatography 1, no. 2: 65-74.

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