Following in Emil Fischer’s Footsteps: A Site-Selective Probe of Glucose Acid–Base Chemistry
Sebastian Malerz, Karen Mudryk, Lukáš Tomaník, Dominik Stemer, U. Hergenhahn, Tillmann Buttersack, Florian Trinter, Robert Seidel, Wilson Quevedo, Claudia Goy, Iain Wilkinson, Stephan Thürmer, Petr Slavı́ček, Bernd Winter
Abstract
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.