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CHIRAL CHROMATOGRAPHIC ANALYSIS AND ABSOLUTE STEREOCHEMISTRY OF RACEMIC CHLORPHENERAMINE USING CHIRAL HPLC-CD-OR AND TD-DFT CALCULATIONS

dc.contributoren-US
dc.creatorMuñoz, Marcelo A.
dc.date2018-09-12
dc.date.accessioned2019-04-16T16:43:01Z
dc.date.available2019-04-16T16:43:01Z
dc.identifierhttps://www.jcchems.com/index.php/JCCHEMS/article/view/777
dc.identifier.urihttp://revistaschilenas.uchile.cl/handle/2250/42461
dc.descriptionA chiral HPLC analysis combined with time-dependent density functional theory (TD-DFT) calculations was used for the assignment of the absolute configuration (AC) of both enantiomers of the antihistamine drug chlorpheniramine. Circular dichroism and optical rotation detections coupled to the chromatographic system (HPLC-CD-OR) permitted the on-line measurement of the CD spectra and [α]670 values, while TD-DFT at the B3LYP/TZVP//B3LYP/VDZ(P) and B3LYP/ aug-cc-pVDZ//B3LYP/VDZ(P) levels of theory for CD and OR, respectively, delivered theoretical chiroptical properties in the gas and solution states. Both calculations were consistent in predicting the correct combination of CD spectra and [α]670 sign and therefore permitted the absolute configuration (AC) assignment of the optical isomers. The AC proposed using this methodology agreed with a previous X-ray study.en-US
dc.formatapplication/pdf
dc.languageeng
dc.publisherSociedad Chilena de Químicaen-US
dc.relationhttps://www.jcchems.com/index.php/JCCHEMS/article/view/777/268
dc.rightsCopyright (c) 2018 Journal of the Chilean Chemical Societyen-US
dc.rightshttp://creativecommons.org/licenses/by-nc-sa/4.0en-US
dc.sourceJournal of the Chilean Chemical Society; Vol 63, No 3 (2018): Journal of the Chilean Chemical Societyen-US
dc.source0717-9707
dc.subjectHPLC-CD-OR; circular dichroism detection; optical rotation detection; DFT calculationsen-US
dc.titleCHIRAL CHROMATOGRAPHIC ANALYSIS AND ABSOLUTE STEREOCHEMISTRY OF RACEMIC CHLORPHENERAMINE USING CHIRAL HPLC-CD-OR AND TD-DFT CALCULATIONSen-US
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/publishedVersion
dc.typeen-US


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