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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Phys. Chem. A 2020, 124, 7, 1240-1252
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    Conformer-Specific Photolysis of Pyruvic Acid and the Effect of Water
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    • Sandra L. Blair
      Sandra L. Blair
      Department of Chemistry, University of Colorado Boulder, UCB 215, Boulder, Colorado 80309, United States
      More by Sandra L. Blair
      Orcidhttp://orcid.org/0000-0003-4130-2403
    • Allison E. Reed Harris
      Allison E. Reed Harris
      Department of Chemistry, University of Colorado Boulder, UCB 215, Boulder, Colorado 80309, United States
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      Orcidhttp://orcid.org/0000-0002-1731-1687
    • Benjamin N. Frandsen
      Benjamin N. Frandsen
      Department of Chemistry, University of Colorado Boulder, UCB 215, Boulder, Colorado 80309, United States
      Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen Ø, Denmark
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    • Henrik G. Kjaergaard
      Henrik G. Kjaergaard
      Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen Ø, Denmark
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      Orcidhttp://orcid.org/0000-0002-7275-8297
    • Edouard Pangui
      Edouard Pangui
      Laboratoire Interuniversitaire des Systèmes Atmosphériques (LISA), UMR CNRS 7583, Institut Pierre Simon Laplace (IPSL), Université Paris-Est Créteil (UPEC) et Université de Paris (UP), 94010 Créteil, France
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    • Mathieu Cazaunau
      Mathieu Cazaunau
      Laboratoire Interuniversitaire des Systèmes Atmosphériques (LISA), UMR CNRS 7583, Institut Pierre Simon Laplace (IPSL), Université Paris-Est Créteil (UPEC) et Université de Paris (UP), 94010 Créteil, France
      More by Mathieu Cazaunau
    • Jean-Francois Doussin
      Jean-Francois Doussin
      Laboratoire Interuniversitaire des Systèmes Atmosphériques (LISA), UMR CNRS 7583, Institut Pierre Simon Laplace (IPSL), Université Paris-Est Créteil (UPEC) et Université de Paris (UP), 94010 Créteil, France
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      Orcidhttp://orcid.org/0000-0002-8042-7228
    • Veronica Vaida*
      Veronica Vaida
      Department of Chemistry, University of Colorado Boulder, UCB 215, Boulder, Colorado 80309, United States
      Cooperative Institute for Research in Environmental Sciences, University of Colorado Boulder, UCB 216, Boulder, Colorado 80309, United States
      *E-mail: [email protected]
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      Orcidhttp://orcid.org/0000-0001-5863-8056
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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2020, 124, 7, 1240–1252
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    https://doi.org/10.1021/acs.jpca.9b10613
    Published January 24, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    The conformer-specific reactivity of gas-phase pyruvic acid following the S1(nπ*) ← S0 excitation at λmax = 350 nm (290–380 nm) and the effect of water are investigated for the two lowest energy conformers. Conformer-specific gas-phase pyruvic acid photolysis rate constants and their respective populations are measured by monitoring their distinct vibrational OH-stretching frequencies. The geometry, relative energies, fundamental vibrational frequencies, and electronic transitions of the pyruvic acid conformers and their monohydrated complexes are calculated with density functional theory and ab initio methods. Results from experiment and theory show that the more stable conformer with an intramolecular hydrogen bond dominates the gas-phase photolysis of pyruvic acid. Water greatly affects the gas-phase pyruvic acid conformer population and photochemistry through hydrogen bonding interactions. The addition of water decreases the gas-phase relative population of the more stable conformer and decreases the molecule’s gas-phase photolysis rate constants. The theoretical results show that even a single water molecule interrupts the intramolecular hydrogen bond, which is essential for the efficient photodissociation of gas-phase pyruvic acid. Results of this study suggest that the aqueous-phase photochemistry of pyruvic acid proceeds through hydrogen-bonded conformers lacking an intramolecular hydrogen bond.

    Copyright © 2020 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jpca.9b10613.

    • Computational section contains a link to an electronic archive of raw computational data, optimized geometries (Figures S1 and S2), bond distances and angles (Figure S3), vibrational frequencies (Tables S1–S4), energies (Tables S5–S8), and vertical excitation energies (Tables S10 and S11) of Tc, Tt, and their monohydrates; geometry (Figures S1, S2, and S4) and energy (Tables S5, S6, and S9) calculations for two enol tautomers, two diol conformers, and dimers of the three lowest energy conformers (Tc, Tt, and Ct) were also investigated and discussed; experimental section contains photolysis rate constants (Figures S5 and S6 and Tables S12 and S13) and conformer populations (Tables S14 and S15) of pyruvic acid; and calculations of atmospherically scaled experimental photolysis rate constants are described in the additional calculation section with final values listed in Table S16 (PDF)

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    Cited By

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    This article is cited by 24 publications.

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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2020, 124, 7, 1240–1252
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jpca.9b10613
    Published January 24, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

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