News Release

UCR chemists identify organic molecules that mimic metals

Molecules may offer solution to storing hydrogen and producing abundant amino compounds for industrial applications

Peer-Reviewed Publication

University of California - Riverside

RIVERSIDE, Calif. -- A limitation in using hydrogen as a fuel in hydrogen-powered vehicles is the difficulty involved in storing it in a cost-effective and convenient manner. While it is possible to store hydrogen using metals, the resulting products often can be prohibitively expensive and cause environmental problems.

Chemists at UC Riverside now offer a possible solution. A class of carbenes – molecules that have unusual, highly reactive carbon atoms – can mimic, to some extent, the behavior of metals, the chemists have found. Called cyclic alkyl amino carbenes or CAACs, these organic molecules, the researchers report, could be used to develop carbon-based systems for storing hydrogen.

Study results appear in the April 20 issue of Science.

In their experiments, the researchers found that the CAACs can split hydrogen under extremely mild conditions, a behavior that has long been seen in metals reacting with hydrogen.

"The mode of action of these organic molecules, however, is totally different from that of metals," said Guy Bertrand, a distinguished professor of chemistry who led the research. "Moreover, the CAACs are able to split ammonia as well – an extremely difficult task for metals."

Bertrand explained that such a splitting of ammonia, under certain conditions, can pave the way for transforming abundant and inexpensive ammonia into useful amino compounds used to make pharmaceuticals and bulk industrial materials. "This is one of the top challenges for the 21st century," he said.

According to the UCR research team, the metal-mimicking carbenes offer another low-cost and low-toxicity benefit: Scientists now may be able to use non-metallic catalysts for a reaction, called "hydrogenation reaction," which plays a critical role in the food, petrochemical and pharmaceutical industries.

In their study, the researchers exposed a solution of CAACs to both gaseous hydrogen and liquid ammonia. "We used nuclear magnetic resonance spectroscopy to analyze the products," said Guido Frey, the first author of the research paper and a postdoctoral fellow, supported by the Alexander von Humboldt Foundation, in Bertrand’s lab. "And we used single crystal X-ray diffraction analysis to confirm the structure of the products."

A carbene is a molecule that has a carbon atom with six electrons instead of the usual eight. Because of the electron deficiency, carbenes are highly reactive and usually unstable in nature.

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The National Science Foundation and Rhodia, Inc., provided support for the study. Bertrand and Frey were joined in the research by the following individuals at UCR: Vincent Lavallo, a graduate student; Bruno Donnadieu, a research associate supported by the Centre National de la Recherche Scientifique; and Wolfgang Schoeller, an adjunct professor of chemistry.

The University of California, Riverside is a doctoral research university, a living laboratory for groundbreaking exploration of issues critical to Inland Southern California, the state and communities around the world. Reflecting California's diverse culture, UCR's enrollment of about 17,000 is projected to grow to 21,000 students by 2010. The campus is proposing a medical school and already has reached the heart of the Coachella Valley by way of the UCR Palm Desert Graduate Center. With an annual statewide economic impact of nearly $1 billion, UCR is actively shaping the region's future. To learn more, visit www.ucr.edu or call (951) UCR-NEWS.


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