Liquid-jet photoelectron spectroscopy was applied to determine the first acid dissociation constant (pKa) of aqueous-phase glucose while simultaneously identifying the spectroscopic signature of the respective deprotonation site. Valence spectra from solutions at pH values below and above the first pKa reveal a change in glucose's lowest ionization energy upon the deprotonation of neutral glucose and the subsequent emergence of its anionic counterpart. Site-specific insights into the solution-pH-dependent molecular structure changes are also shown to be accessible via C 1s photoelectron spectroscopy. The spectra reveal a considerably lower C 1s binding energy of the carbon site associated with the deprotonated hydroxyl group. The occurrence of photoelectron spectral fingerprints of cyclic and linear glucose prior to and upon deprotonation are also discussed. The experimental data are interpreted with the aid of electronic structure calculations. Our findings highlight the potential of liquid-jet photoelectron spectroscopy to act as a site-selective probe of the molecular structures that underpin the acid-base chemistry of polyprotic systems with relevance to environmental chemistry and biochemistry.

Centre for Molecular Water Science Notkestraße 85 22607 Hamburg Germany

Department of Chemistry Graduate School of Science Kyoto University Kitashirakawa Oiwakecho Sakyo Ku Kyoto 606 8502 Japan

Department of Locally Sensitive and Time Resolved Spectroscopy Helmholtz Zentrum Berlin für Materialien und Energie Hahn Meitner Platz 1 14109 Berlin Germany

Department of Physical Chemistry University of Chemistry and Technology Technická 5 Prague 6 16628 Czech Republic

Fritz Haber Institut der Max Planck Gesellschaft Faradayweg 4 6 14195 Berlin Germany

Institut für Chemie Humboldt Universität zu Berlin Brook Taylor Str 2 12489 Berlin Germany

Institut für Kernphysik Goethe Universität Max von Laue Straße 1 60438 Frankfurt am Main Germany

Operando Interfacial Photochemistry Helmholtz Zentrum Berlin für Materialien und Energie Albert Einstein Straße 15 12489 Berlin Germany

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