ABSOLUTE CONFIGURATION ASSIGNMENT IN RACEMIC trans-STILBENE OXIDE USING CHIRAL LIQUID CHROMATOGRAPHY WITH COMBINED CHIROPTICAL DETECTION AND TIME-DEPENDENT DENSITY FUNCTIONAL THEORY CALCULATIONS
A chiral chromatographic analysis using HPLC coupled in series with circular dichroism and optical rotation detectors (HPLC-CD-OR) was applied to racemic trans-stilbene oxide, allowing the on-line measurement of the CD spectra and [α] values for both enantiomers in the sample. These measure...
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Sociedad Chilena de Química
2016
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oai:scielo:S0717-970720160001000062016-09-14ABSOLUTE CONFIGURATION ASSIGNMENT IN RACEMIC trans-STILBENE OXIDE USING CHIRAL LIQUID CHROMATOGRAPHY WITH COMBINED CHIROPTICAL DETECTION AND TIME-DEPENDENT DENSITY FUNCTIONAL THEORY CALCULATIONSCASTILLO-GONZÁLEZ,JUAN PGONZÁLEZ-PEÑA,NATALIA IMUÑOZ,MARCELO AA chiral chromatographic analysis using HPLC coupled in series with circular dichroism and optical rotation detectors (HPLC-CD-OR) was applied to racemic trans-stilbene oxide, allowing the on-line measurement of the CD spectra and [α] values for both enantiomers in the sample. These measurementsused the Gaussian peak model to estimate the concentration of each isomer in the CD and OR cells. Moreover, time-dependent density functional theory (TD-DFT) calculations at the B3LYP/TZVP//B3LYP/VDZ(P) and B3LYP/aug-cc-pVDZ//B3LYP/VDZ(P) levels of the ory for CD and OR, respectively, permitted the prediction of both chiroptical properties for each isomer, which in turn could be compared with the corresponding experimental data. In this case, the calculationswere consistent in predicting the correct combination of experimental CD bands and [a] sign and the refore facilitated the absolute configuration (AC) assignment of the optical isomers. The AC proposed using this methodology was in agreement with independent AC assignments in the literature.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.61 n.1 20162016-03-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072016000100006en10.4067/S0717-97072016000100006 |
| institution |
Scielo Chile |
| collection |
Scielo Chile |
| language |
English |
| description |
A chiral chromatographic analysis using HPLC coupled in series with circular dichroism and optical rotation detectors (HPLC-CD-OR) was applied to racemic trans-stilbene oxide, allowing the on-line measurement of the CD spectra and [α] values for both enantiomers in the sample. These measurementsused the Gaussian peak model to estimate the concentration of each isomer in the CD and OR cells. Moreover, time-dependent density functional theory (TD-DFT) calculations at the B3LYP/TZVP//B3LYP/VDZ(P) and B3LYP/aug-cc-pVDZ//B3LYP/VDZ(P) levels of the ory for CD and OR, respectively, permitted the prediction of both chiroptical properties for each isomer, which in turn could be compared with the corresponding experimental data. In this case, the calculationswere consistent in predicting the correct combination of experimental CD bands and [a] sign and the refore facilitated the absolute configuration (AC) assignment of the optical isomers. The AC proposed using this methodology was in agreement with independent AC assignments in the literature. |
| author |
CASTILLO-GONZÁLEZ,JUAN P GONZÁLEZ-PEÑA,NATALIA I MUÑOZ,MARCELO A |
| spellingShingle |
CASTILLO-GONZÁLEZ,JUAN P GONZÁLEZ-PEÑA,NATALIA I MUÑOZ,MARCELO A ABSOLUTE CONFIGURATION ASSIGNMENT IN RACEMIC trans-STILBENE OXIDE USING CHIRAL LIQUID CHROMATOGRAPHY WITH COMBINED CHIROPTICAL DETECTION AND TIME-DEPENDENT DENSITY FUNCTIONAL THEORY CALCULATIONS |
| author_facet |
CASTILLO-GONZÁLEZ,JUAN P GONZÁLEZ-PEÑA,NATALIA I MUÑOZ,MARCELO A |
| author_sort |
CASTILLO-GONZÁLEZ,JUAN P |
| title |
ABSOLUTE CONFIGURATION ASSIGNMENT IN RACEMIC trans-STILBENE OXIDE USING CHIRAL LIQUID CHROMATOGRAPHY WITH COMBINED CHIROPTICAL DETECTION AND TIME-DEPENDENT DENSITY FUNCTIONAL THEORY CALCULATIONS |
| title_short |
ABSOLUTE CONFIGURATION ASSIGNMENT IN RACEMIC trans-STILBENE OXIDE USING CHIRAL LIQUID CHROMATOGRAPHY WITH COMBINED CHIROPTICAL DETECTION AND TIME-DEPENDENT DENSITY FUNCTIONAL THEORY CALCULATIONS |
| title_full |
ABSOLUTE CONFIGURATION ASSIGNMENT IN RACEMIC trans-STILBENE OXIDE USING CHIRAL LIQUID CHROMATOGRAPHY WITH COMBINED CHIROPTICAL DETECTION AND TIME-DEPENDENT DENSITY FUNCTIONAL THEORY CALCULATIONS |
| title_fullStr |
ABSOLUTE CONFIGURATION ASSIGNMENT IN RACEMIC trans-STILBENE OXIDE USING CHIRAL LIQUID CHROMATOGRAPHY WITH COMBINED CHIROPTICAL DETECTION AND TIME-DEPENDENT DENSITY FUNCTIONAL THEORY CALCULATIONS |
| title_full_unstemmed |
ABSOLUTE CONFIGURATION ASSIGNMENT IN RACEMIC trans-STILBENE OXIDE USING CHIRAL LIQUID CHROMATOGRAPHY WITH COMBINED CHIROPTICAL DETECTION AND TIME-DEPENDENT DENSITY FUNCTIONAL THEORY CALCULATIONS |
| title_sort |
absolute configuration assignment in racemic trans-stilbene oxide using chiral liquid chromatography with combined chiroptical detection and time-dependent density functional theory calculations |
| publisher |
Sociedad Chilena de Química |
| publishDate |
2016 |
| url |
http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072016000100006 |
| work_keys_str_mv |
AT castillogonzalezjuanp absoluteconfigurationassignmentinracemictransstilbeneoxideusingchiralliquidchromatographywithcombinedchiropticaldetectionandtimedependentdensityfunctionaltheorycalculations AT gonzalezpenanataliai absoluteconfigurationassignmentinracemictransstilbeneoxideusingchiralliquidchromatographywithcombinedchiropticaldetectionandtimedependentdensityfunctionaltheorycalculations AT munozmarceloa absoluteconfigurationassignmentinracemictransstilbeneoxideusingchiralliquidchromatographywithcombinedchiropticaldetectionandtimedependentdensityfunctionaltheorycalculations |
| _version_ |
1718445546661740544 |