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Issue 32, 2016
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Photofragmentation mechanisms in protonated chiral cinchona alkaloids

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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

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Publication details

The article was received on 10 Jun 2016, accepted on 19 Jul 2016 and first published on 21 Jul 2016


Article type: Paper
DOI: 10.1039/C6CP04041A
Citation: Phys. Chem. Chem. Phys., 2016,18, 22668-22677
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    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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