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Exotic Protonated Species Produced by UV-Induced Photofragmentation of a Protonated Dimer: Metastable Protonated Cinchonidine
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    Exotic Protonated Species Produced by UV-Induced Photofragmentation of a Protonated Dimer: Metastable Protonated Cinchonidine
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    Institut des Sciences Moléculaires d’Orsay (ISMO), CNRS, Univ Paris-Sud, Université Paris Saclay, F-91405 Orsay, France
    Laboratoire de Chimie Physique (LCP), CNRS, Univ Paris-Sud, Université Paris Saclay, F-91405 Orsay, France
    *A. Zehnacker-Rentien. E-mail: [email protected]
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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2015, 119, 39, 10007–10015
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    https://doi.org/10.1021/acs.jpca.5b06506
    Published September 8, 2015
    Copyright © 2015 American Chemical Society

    Abstract

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    A metastable protonated cinchona alkaloid was produced in the gas phase by UV-induced photodissociation (UVPD) of its protonated dimer in a Paul ion trap. The infrared multiple photon dissociation (IRMPD) spectrum of the molecular ion formed by UVPD was obtained and compared to DFT calculations to characterize its structure. The protonation site obtained thereby is not accessible by classical protonation ways. The protonated monomer directly formed in the ESI source or by collision-induced dissociation (CID) of the dimer undergoes protonation at the most basic alkaloid nitrogen. In contrast, protonation occurs at the quinoline aromatic ring nitrogen in the UVPD-formed monomer.

    Copyright © 2015 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jpca.5b06506.

    • Table of relative energies, figure of geometries, and simulated spectra for additional structures, simulated spectra of structures listed in Table 1 but not given in Figure 3 (PDF)

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    This article is cited by 4 publications.

    1. Rina Ibragimova, Mikhail S. Kuklin, Tigany Zarrouk, Miguel A. Caro. Unifying the Description of Hydrocarbons and Hydrogenated Carbon Materials with a Chemically Reactive Machine Learning Interatomic Potential. Chemistry of Materials 2025, 37 (3) , 1094-1110. https://doi.org/10.1021/acs.chemmater.4c02905
    2. Feriel Ben Nasr, Ivan Alata, Debora Scuderi, Valeria Lepère, Valerie Brenner, Nejm-Eddine Jaïdane, Anne Zehnacker. Effects of complexation with sulfuric acid on the photodissociation of protonated Cinchona alkaloids in the gas phase. Physical Chemistry Chemical Physics 2019, 21 (28) , 15439-15451. https://doi.org/10.1039/C9CP01518C
    3. Aude Bouchet, Johanna Klyne, Shun-ichi Ishiuchi, Otto Dopfer, Masaaki Fujii, Anne Zehnacker. Stereochemistry-dependent structure of hydrogen-bonded protonated dimers: the case of 1-amino-2-indanol. Physical Chemistry Chemical Physics 2018, 20 (18) , 12430-12443. https://doi.org/10.1039/C8CP00787J
    4. Sunil Kumar, Bruno Lucas, Jacqueline Fayeton, Debora Scuderi, Ivan Alata, Michel Broquier, Katia Le Barbu-Debus, Valeria Lepère, Anne Zehnacker. Photofragmentation mechanisms in protonated chiral cinchona alkaloids. Physical Chemistry Chemical Physics 2016, 18 (32) , 22668-22677. https://doi.org/10.1039/C6CP04041A

    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2015, 119, 39, 10007–10015
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jpca.5b06506
    Published September 8, 2015
    Copyright © 2015 American Chemical Society

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