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Accueil du site > Production scientifique > Probing the gas-phase structure of charge-tagged intermediates of a proline catalyzed aldol reaction - vibrational spectroscopy distinguishes oxazolidinone from enamine species

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

Date de publication: 7 janvier 2019

J.A. Willms ; J. Vidic ; J. Barthelmes ; V. Steinmetz ; T. Bredow ; P. Maitre ; M. Engeser
Phys. Chem. Chem. Phys. 21 (5) 2578-2586 (2019). DOI

Travail réalisé sur le site de l’Université Paris Sud.

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.