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  Following in Emil Fischer’s Footsteps: A Site-Selective Probe of Glucose Acid–Base Chemistry

Malerz, S., Mudryk, K., Tomaník, L., Stemer, D., Hergenhahn, U., Buttersack, T., et al. (2021). Following in Emil Fischer’s Footsteps: A Site-Selective Probe of Glucose Acid–Base Chemistry. The Journal of Physical Chemistry A, 125(32), 6881-6892. doi:10.1021/acs.jpca.1c04695.

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 Creators:
Malerz, Sebastian1, Author              
Mudryk, Karen1, Author              
Tomaník, Lukáš2, Author
Stemer, Dominik1, Author              
Hergenhahn, Uwe1, Author              
Buttersack, Tillmann1, Author              
Trinter, Florian1, 3, Author              
Seidel, Robert4, 5, Author
Quevedo, Wilson4, Author
Goy, Claudia6, Author
Wilkinson, Iain7, Author
Thürmer, Stephan8, Author
Slavíček, Petr2, Author
Winter, Bernd1, Author              
Affiliations:
1Molecular Physics, Fritz Haber Institute, Max Planck Society, ou_634545              
2Department of Physical Chemistry, University of Chemistry and Technology, Technická 5, Prague 6 16628, Czech Republic, ou_persistent22              
3Institut für Kernphysik, Goethe-Universität, Max-von-Laue-Straße 1, 60438 Frankfurt am Main, Germany, ou_persistent22              
4Operando Interfacial Photochemistry, Helmholtz-Zentrum Berlin für Materialien und Energie, Albert-Einstein-Straße 15, 12489 Berlin, Germany, ou_persistent22              
5Institut für Chemie, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489 Berlin, Germany, ou_persistent22              
6Centre for Molecular Water Science (CMWS), Photon Science, Deutsches Elektronen-Synchrotron (DESY), Notkestraße 85, 22607 Hamburg, Germany, ou_persistent22              
7Department of Locally-Sensitive & Time-Resolved Spectroscopy, Helmholtz-Zentrum Berlin für Materialien und Energie, Hahn-Meitner-Platz 1, 14109 Berlin, Germany, ou_persistent22              
8Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa-Oiwakecho, Sakyo-Ku, Kyoto 606-8502, Japan, ou_persistent22              

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 Abstract: 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.

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Language(s): eng - English
 Dates: 2021-05-282021-07-302021-08-19
 Publication Status: Published in print
 Pages: 12
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.jpca.1c04695
 Degree: -

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Project name : AQUACHIRAL - Chiral aqueous-phase chemistry
Grant ID : 883759
Funding program : Horizon 2020 (H2020)
Funding organization : European Commission (EC)

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Title: The Journal of Physical Chemistry A
  Other : J. Phys. Chem. A
Source Genre: Journal
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Publ. Info: Columbus, OH : American Chemical Society
Pages: 12 Volume / Issue: 125 (32) Sequence Number: - Start / End Page: 6881 - 6892 Identifier: ISSN: 1089-5639
CoNE: https://pure.mpg.de/cone/journals/resource/954926947766_4