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

ABSTRACT A 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 th...

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Autor principal:	Muñoz,Marcelo A.
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2018
Materias:	HPLC-CD-OR circular dichroism detection optical rotation detection DFT calculations
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000304155
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spelling	oai:scielo:S0717-970720180003041552018-10-03CHIRAL CHROMATOGRAPHIC ANALYSIS AND ABSOLUTE STEREOCHEMISTRY OF RACEMIC CHLORPHENERAMINE USING CHIRAL HPLC-CD-OR AND TD-DFT CALCULATIONSMuñoz,Marcelo A. HPLC-CD-OR circular dichroism detection optical rotation detection DFT calculations ABSTRACT A 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.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.63 n.3 20182018-01-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000304155en10.4067/s0717-97072018000304155
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	HPLC-CD-OR circular dichroism detection optical rotation detection DFT calculations
spellingShingle	HPLC-CD-OR circular dichroism detection optical rotation detection DFT calculations Muñoz,Marcelo A. CHIRAL CHROMATOGRAPHIC ANALYSIS AND ABSOLUTE STEREOCHEMISTRY OF RACEMIC CHLORPHENERAMINE USING CHIRAL HPLC-CD-OR AND TD-DFT CALCULATIONS
description	ABSTRACT A 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.
author	Muñoz,Marcelo A.
author_facet	Muñoz,Marcelo A.
author_sort	Muñoz,Marcelo A.
title	CHIRAL CHROMATOGRAPHIC ANALYSIS AND ABSOLUTE STEREOCHEMISTRY OF RACEMIC CHLORPHENERAMINE USING CHIRAL HPLC-CD-OR AND TD-DFT CALCULATIONS
title_short	CHIRAL CHROMATOGRAPHIC ANALYSIS AND ABSOLUTE STEREOCHEMISTRY OF RACEMIC CHLORPHENERAMINE USING CHIRAL HPLC-CD-OR AND TD-DFT CALCULATIONS
title_full	CHIRAL CHROMATOGRAPHIC ANALYSIS AND ABSOLUTE STEREOCHEMISTRY OF RACEMIC CHLORPHENERAMINE USING CHIRAL HPLC-CD-OR AND TD-DFT CALCULATIONS
title_fullStr	CHIRAL CHROMATOGRAPHIC ANALYSIS AND ABSOLUTE STEREOCHEMISTRY OF RACEMIC CHLORPHENERAMINE USING CHIRAL HPLC-CD-OR AND TD-DFT CALCULATIONS
title_full_unstemmed	CHIRAL CHROMATOGRAPHIC ANALYSIS AND ABSOLUTE STEREOCHEMISTRY OF RACEMIC CHLORPHENERAMINE USING CHIRAL HPLC-CD-OR AND TD-DFT CALCULATIONS
title_sort	chiral chromatographic analysis and absolute stereochemistry of racemic chlorpheneramine using chiral hplc-cd-or and td-dft calculations
publisher	Sociedad Chilena de Química
publishDate	2018
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000304155
work_keys_str_mv	AT munozmarceloa chiralchromatographicanalysisandabsolutestereochemistryofracemicchlorpheneramineusingchiralhplccdorandtddftcalculations
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CHIRAL CHROMATOGRAPHIC ANALYSIS AND ABSOLUTE STEREOCHEMISTRY OF RACEMIC CHLORPHENERAMINE USING CHIRAL HPLC-CD-OR AND TD-DFT CALCULATIONS

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