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Molecules 2014, 19(12), 21489-21505;

Transfer Hydrogenation in Open-Shell Nucleotides — A Theoretical Survey

Department of Chemistry, Ludwig-Maximilians-Universität Munich, Butenandtstr. 5–13, Munich 81377, Germany
Author to whom correspondence should be addressed.
Received: 13 November 2014 / Revised: 8 December 2014 / Accepted: 11 December 2014 / Published: 22 December 2014
(This article belongs to the Special Issue Free Radicals and Radical Ions)
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The potential of a larger number of sugar models to act as dihydrogen donors in transfer hydrogenation reactions has been quantified through the calculation of hydrogenation energies of the respective oxidized products. Comparison of the calculated energies to hydrogenation energies of nucleobases shows that many sugar fragment radicals can reduce pyrimidine bases such as uracil in a strongly exothermic fashion. The most potent reducing agent is the C3' ribosyl radical. The energetics of intramolecular transfer hydrogenation processes has also been calculated for a number of uridinyl radicals. The largest driving force for such a process is found for the uridin-C3'-yl radical, whose rearrangement to the C2'-oxidized derivative carrying a dihydrouracil is predicted to be exothermic by 61.1 kJ/mol in the gas phase. View Full-Text
Keywords: transfer hydrogenation; open-shell nucleotides; thermochemistry; heats of hydrogenation; radical stabilization energy transfer hydrogenation; open-shell nucleotides; thermochemistry; heats of hydrogenation; radical stabilization energy

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Achrainer, F.; Zipse, H. Transfer Hydrogenation in Open-Shell Nucleotides — A Theoretical Survey. Molecules 2014, 19, 21489-21505.

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