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Enantioseparation of four amide herbicide stereoisomers using high-performance liquid chromatography

Xie, Jingqian and Zhao, Lu and Liu, Kai and Guo, Fangjie and Liu, Weiping (2016) Enantioseparation of four amide herbicide stereoisomers using high-performance liquid chromatography. Journal of Chromatography A, 1471 . pp. 145-154. ISSN 0021-9673. http://resolver.caltech.edu/CaltechAUTHORS:20161031-084636085

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Abstract

The chirality of herbicides has been the focus of research. However, there is little information on the enantioseparation of amide herbicides with different chiral elements. In this study, the need for different chiral stationary phases (CSPs), mobile phases, temperatures and flow rates for the separation of napropamide, acetochlor and propisochlor was discussed in detail and compared to metolachlor. Resolution of C-chiral enantiomers was easier than that of axial-chiral enantiomers. Metolachlor and acetochlor could achieve baseline separation only on AY-H and AS-H columns, respectively. Propisochlor had satisfactory separations on OD-H and AS-H columns. Napropamide was separated on OJ-H, AY-H and AS-H columns. Both the structures of the compounds and CSPs and the interactions between them played significant roles in the enantioseparations. Molecule dockings were also used to elucidate the separation mechanisms. C-chiral enantiomers had perfect symmetry in their optical properties, whereas the axial-chiral enantiomers did not. The elution order for napropamide, acetochlor and propisochlor, with a single chiral location, was R- prior to S-. These results were the first that compare the enantioseparations of four amide herbicides with different chirality, and they provided the absolute configurations for the herbicides. The paper also illustrated certain mechanisms for enantioseparations.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/j.chroma.2016.10.029DOIArticle
http://www.sciencedirect.com/science/article/pii/S0021967316313760PublisherArticle
ORCID:
AuthorORCID
Liu, Weiping0000-0002-1173-892X
Additional Information:© 2016 Elsevier B.V. Received 5 August 2016, Revised 9 October 2016, Accepted 11 October 2016, Available online 13 October 2016.
Subject Keywords:Chirality; Amide herbicides; Enantioseparation; Absolute configuration; Separation mechanisms
Record Number:CaltechAUTHORS:20161031-084636085
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20161031-084636085
Official Citation:Jingqian Xie, Lu Zhao, Kai Liu, Fangjie Guo, Weiping Liu, Enantioseparation of four amide herbicide stereoisomers using high-performance liquid chromatography, Journal of Chromatography A, Volume 1471, 4 November 2016, Pages 145-154, ISSN 0021-9673, http://dx.doi.org/10.1016/j.chroma.2016.10.029. (http://www.sciencedirect.com/science/article/pii/S0021967316313760)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:71604
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:31 Oct 2016 15:56
Last Modified:17 Apr 2017 19:25

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