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Dr. George Tsilomelekis, Tyler R. Josephson, Dr. Vladimiros Nikolakis and Dr. Stavros Caratzoulas Origin of 5-Hydroxymethylfurfural Stability in Water/Dimethyl Sulfoxide Mixtures ChemSusChem 7

Article first published online: 10 JAN 2014 | DOI: 10.1002/cssc.201300786

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To HMF with it! 5-Hydroxymethylfurfural (HMF) solvation by DMSO increases its LUMO energy and thus reduces its susceptibility to nucleophilic attack, which minimizes undesirable hydration and humin-formation reactions. DMSO preferentially solvates the HMF carbonyl group over water, which provides an explanation for the enhanced HMF stability in DMSO/water mixtures observed experimentally.

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