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Issue 5, 2019
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Probing the gas-phase structure of charge-tagged intermediates of a proline catalyzed aldol reaction – vibrational spectroscopy distinguishes oxazolidinone from enamine species

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Abstract

An L-proline based catalyst with a charged phenyl-pyridium substituent (1) was used to analyze intermediates of an organocatalyzed aldol reaction by infrared multi-photon dissociation (IRMPD) mass spectrometry after transfer into the gas phase via electrospray ionization (ESI). IRMPD spectra were interpreted with the aid of density functional theory (DFT) computations. A structurally restricted enamine species was used as a reference molecule for the calculated vibrational frequencies. A close correlation between theory and experiment was found for the energetically most favoured oxazolidinone structures.

Graphical abstract: Probing the gas-phase structure of charge-tagged intermediates of a proline catalyzed aldol reaction – vibrational spectroscopy distinguishes oxazolidinone from enamine species

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Publication details

The article was received on 01 Aug 2018, accepted on 05 Jan 2019 and first published on 07 Jan 2019


Article type: Paper
DOI: 10.1039/C8CP04905J
Citation: Phys. Chem. Chem. Phys., 2019,21, 2578-2586

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    Probing the gas-phase structure of charge-tagged intermediates of a proline catalyzed aldol reaction – vibrational spectroscopy distinguishes oxazolidinone from enamine species

    J. A. Willms, J. Vidic, J. Barthelmes, V. Steinmetz, T. Bredow, P. Maître and M. Engeser, Phys. Chem. Chem. Phys., 2019, 21, 2578
    DOI: 10.1039/C8CP04905J

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