Jump to main content
Jump to site search

Issue 5, 2019
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
01 Aug 2018
Accepted
05 Jan 2019
First published
07 Jan 2019

Phys. Chem. Chem. Phys., 2019,21, 2578-2586
Article type
Paper

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

Social activity

Search articles by author

Spotlight

Advertisements