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Open AccessArticle

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

Department of Chemistry and Biochemistry, Baylor University, Waco, TX 76798, USA
Author to whom correspondence should be addressed.
Chromatography 2014, 1(2), 65-74;
Received: 3 April 2014 / Revised: 9 May 2014 / Accepted: 12 May 2014 / Published: 16 May 2014
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. View Full-Text
Keywords: chiral azulene; chiral high-pressure liquid chromatography; enantioseparation 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.

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