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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 186, 2011 - Issue 5: 24th International Symposium on the Organic Chemistry of Sulfur
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Oral Contributions

Catalysis of Electrochemical Reduction of Weak Acids to Produce H2: Role of O‒H…S Hydrogen Bonding

Dr Jinzhu Chen Department of Chemistry and Biochemistry, The University of Arizona, Tucson, Arizona, USA
,
Dr Aaron K. Vannucci Department of Chemistry and Biochemistry, The University of Arizona, Tucson, Arizona, USA
,
Dr Charles A. Mebi Department of Chemistry and Biochemistry, The University of Arizona, Tucson, Arizona, USA
,
Dr Noriko Okumura Department of Chemistry and Biochemistry, The University of Arizona, Tucson, Arizona, USA
,
Ms Susan C. Borowski Department of Chemistry and Biochemistry, The University of Arizona, Tucson, Arizona, USA
,
Dr L. Tori Lockett Department of Chemistry and Biochemistry, The University of Arizona, Tucson, Arizona, USA
,
Mr Matthew Swenson Department of Chemistry and Biochemistry, The University of Arizona, Tucson, Arizona, USA
,
Professor Dennis L. Lichtenberger Department of Chemistry and Biochemistry, The University of Arizona, Tucson, Arizona, USA
,
Professor Dennis H. Evans Department of Chemistry and Biochemistry, The University of Arizona, Tucson, Arizona, USA
&
Professor Richard S. Glass Department of Chemistry and Biochemistry, The University of Arizona, Tucson, Arizona, USA
 show all
Pages 1288-1292 | Received 17 Aug 2010, Accepted 09 Sep 2010, Published online: 12 Jul 2011
 
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Abstract

The role of intramolecular OH…S hydrogen bonding in the electrochemical reduction of protons from acetic acid using biomimetically inspired catalysts has been studied. The catalysts, hydroquinone moieties annulated to an Fe2S2(CO)6 core, were synthesized by piperidine-mediated conjugate addition of the dithiol Fe2(SH)2(CO)6 to quinones in 26–76% yields. These complexes catalyze electrochemical H2 production from acetic acid. Evidence for weak intramolecular OH…S hydrogen bonding in the neutral complexes is presented. Such hydrogen bonding becomes stronger as the charge increases on the sulfur in the electrochemically produced dianions due to “charge assistance,” and this has chemical consequences.

Acknowledgments

The support of this research by the U.S. National Science Foundation is gratefully acknowledged.

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