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Conformational Analysisof Quinine and Its PseudoEnantiomer Quinidine: A Combined Jet-Cooled Spectroscopy and VibrationalCircular Dichroism Study.

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Title: Conformational Analysisof Quinine and Its PseudoEnantiomer Quinidine: A Combined Jet-Cooled Spectroscopy and VibrationalCircular Dichroism Study.
Authors: Sen, Ananya1, Bouchet, Aude1, Lepère, Valeria1, Le Barbu-Debus, Katia1, Scuderi, D.1, Piuzzi, F.1, Zehnacker-Rentien, A.1
Source: Journal of Physical Chemistry A. Aug2012, Vol. 116 Issue 32, p8334-8344. 11p.
Subjects: Quinine, Enantiomers, Quinidine, Vibrational circular dichroism, Conformational analysis, Laser spectroscopy
Abstract: Laser-desorbed quinine and quinidine have been studiedin the gasphase by combining supersonic expansion with laser spectroscopy, namely,laser-induced fluorescence (LIF), resonance-enhanced multiphoton ionization(REMPI), and IR-UV double resonance experiments. Density funtionaltheory (DFT) calculations have been done in conjunction with the experimentalwork. The first electronic transition of quinine and quinidine isof π–π* nature, and the studied molecules weaklyfluoresce in the gas phase, in contrast to what was observed in solution(Qin, W. W.; et al. J. Phys. Chem. C2009, 113, 11790). The two pseudo enantiomers quinineand quinidine show limited differences in the gas phase; their mainconformation is of open type as it is in solution. However, vibrationalcircular dichroism (VCD) experiments in solution show that additionalconformers exist in condensed phase for quinidine, which are not observedfor quinine. This difference in behavior between the two pseudo enantiomersis discussed. [ABSTRACT FROM AUTHOR]
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Database: Engineering Source
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Abstract:Laser-desorbed quinine and quinidine have been studiedin the gasphase by combining supersonic expansion with laser spectroscopy, namely,laser-induced fluorescence (LIF), resonance-enhanced multiphoton ionization(REMPI), and IR-UV double resonance experiments. Density funtionaltheory (DFT) calculations have been done in conjunction with the experimentalwork. The first electronic transition of quinine and quinidine isof π–π* nature, and the studied molecules weaklyfluoresce in the gas phase, in contrast to what was observed in solution(Qin, W. W.; et al. J. Phys. Chem. C2009, 113, 11790). The two pseudo enantiomers quinineand quinidine show limited differences in the gas phase; their mainconformation is of open type as it is in solution. However, vibrationalcircular dichroism (VCD) experiments in solution show that additionalconformers exist in condensed phase for quinidine, which are not observedfor quinine. This difference in behavior between the two pseudo enantiomersis discussed. [ABSTRACT FROM AUTHOR]
ISSN:10895639
DOI:10.1021/jp3047888