Probing the gas-phase structure of charge-tagged intermediates of a proline catalyzed aldol reaction – vibrational spectroscopy distinguishes oxazolidinone from enamine species. Issue 5 (18th January 2019)

• Record Type: Journal Article
• Authors: Willms, J. Alexander; Vidic, Jandro; Barthelmes, Janosch; Steinmetz, Vincent; Bredow, Thomas; Maître, Philippe; Engeser, Marianne
• Is Part Of: Physical chemistry chemical physics. Volume 21:Issue 5(2019)
• Page Start: 2578
• Page End: 2586
• Publication Date: 2019-01-18
• Subjects: Chemistry, Physical and theoretical -- Periodicals; 541.3
• DOI: 10.1039/c8cp04905j
• Languages: English
• ISSNs: 1463-9076

Abstract

Abstract : Charge-tagging enables the detection of reaction intermediates which are probed by IRMPD spectroscopy in combination with theory. Abstract : Anl -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.