Solvent Effects on the Intramolecular Hydrogen-Atom Transfer

May 28, 2009 - The Third Dimension of a More O'Ferrall–Jencks Diagram for Hydrogen Atom Transfer in the Isoelectronic Hydrogen Exchange Reactions of...
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J. Phys. Chem. C 2009, 113, 11695–11703

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Solvent Effects on the Intramolecular Hydrogen-Atom Transfer between Tyrosine and Benzophenone. Diverting Reaction Mechanisms in Protic and Nonprotic Media† Gerald Ho¨rner,* Anna Lewandowska, Gordon L. Hug,‡ and Bronislaw Marciniak Faculty of Chemistry, Adam Mickiewicz UniVersity Poznan, Grunwaldzka 6, PL-60-780 Poznan, Poland ReceiVed: February 25, 2009; ReVised Manuscript ReceiVed: May 5, 2009

The intramolecular hydrogen-atom transfer between tyrosine and triplet-excited benzophenone was studied by nanosecond laser-flash photolysis in a number of nonprotic and protic solvents. The reaction rates were found to be strongly solvent dependent with a range from