Issue 32, 2016

Photofragmentation mechanisms in protonated chiral cinchona alkaloids

Abstract

The photo-stability of protonated cinchona alkaloids is studied in the gas phase by a multi-technique approach. A multi-coincidence technique is used to demonstrate that the dissociation is a direct process. Two dissociation channels are observed. They result from the C8–C9 cleavage, accompanied or not by hydrogen migration. The branching ratio between the two photo-fragments is different for the two pseudo-enantiomers quinine and quinidine. Mass spectrometry experiments coupling UV photo-dissociation of the reactants and structural characterization of the ionic photo-products by Infra-Red Multiple Photo-Dissociation (IRMPD) spectroscopy provide unambiguous information on their structure. In addition, quantum chemical calculations allow proposing a reactive scheme and discussing it in terms of the ground-state geometry of the reactant.

Graphical abstract: Photofragmentation mechanisms in protonated chiral cinchona alkaloids

Supplementary files

Article information

Article type
Paper
Submitted
10 Jun 2016
Accepted
19 Jul 2016
First published
21 Jul 2016

Phys. Chem. Chem. Phys., 2016,18, 22668-22677

Photofragmentation mechanisms in protonated chiral cinchona alkaloids

S. Kumar, B. Lucas, J. Fayeton, D. Scuderi, I. Alata, M. Broquier, K. L. Barbu-Debus, V. Lepère and A. Zehnacker, Phys. Chem. Chem. Phys., 2016, 18, 22668 DOI: 10.1039/C6CP04041A

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