Advertisement

If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)

ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.

ENJOY UNLIMITED ACCES TO C&EN

Synthesis

ACS Award For Creative Work In Fluorine Chemistry

Sponsored by Honeywell

by Elizabeth K. Wilson
February 8, 2010 | A version of this story appeared in Volume 88, Issue 6

Hughes
[+]Enlarge
Credit: Joseph Mehling
Credit: Joseph Mehling

Molecules containing carbon-fluorine bonds, ubiquitous in medicine and industry, owe much of their inertness to the unusual strength of these bonds. But the notorious reputation of many perfluorocarbons and chlorofluorocarbons as potent greenhouse gases has prompted the development of what’s hoped will be less environmentally detrimental hydrofluorocarbons.

Russell P. Hughes uses transition-metal complexes to develop stereoselective methods for breaking apart strong C–F bonds and replacing them with C–H and C–C bonds. For example, Hughes, who is the Frank R. Mori Professor of Chemistry at Dartmouth College, has used iridium and rhodium complexes to activate C–F bonds under extremely mild conditions.

But his more recent work with C–F bond activation represents only a subset of decades of creative research he has carried out with fluorine-containing organometallic compounds, his colleagues say. In 1992, he solved one of the most vexing synthetic problems for fluorine chemists: He created a ruthenium complex with a perfluorocyclopentadienyl ligand. “No quest has been more frustrating than the search for a C5F5 complex. Many have tried,” notes Richard R. Schrock, a chemistry professor at Massachusetts Institute of Technology. Hughes pursued an adventurous synthesis, the flash vacuum pyrolysis of an oxoperfluorocyclohexadienyl complex at 750 °C, to produce Ru[C5(CH3)5](C5F5).

“No other chemist has the organic knowledge, mechanistic insight, perseverance, and daring necessary to avoid the traps that nature sets for them in their pursuit of goals that others have declared unattainable,” Schrock observes.

Dartmouth emeritus chemistry professor David M. Lemal, Hughes’s longtime colleague and himself a winner of the ACS Award for Creative Work in Fluorine Chemistry in 2002, notes other synthetic firsts accomplished by the Hughes group: the first perfluorometallacyclobutene, the first perfluorobutatriene complex, the first perfluoroalkylidene complexes, and, most recently, the first complex containing the simplest binary fluorocarbon, carbon monofluoride, as a terminal ligand. “While his research is wide-ranging, it is quite the opposite of ‘cherry picking,’ ” Lemal says. “He strives for full understanding when he addresses a problem.”

Born in 1946 in Denbigh, Wales, Hughes received a bachelor’s degree from the University of Manchester Institute of Science & Technology in 1967. He then studied with John Powell at the University of Toronto, where he received a Ph.D. in chemistry in 1972. After postdoctoral positions at the University of Bristol, in England, with Michael Green and at McGill University, in Canada, with John Harrod, Hughes became an assistant professor at Dartmouth College in 1976. He became a full professor in 1986.

With more than 175 published papers, Hughes has given numerous invited talks throughout the years. He is a fellow of the Royal Society of Chemistry and has also served on the editorial advisory boards of the Journal of Fluorine Chemistry and Organometallics.

Hughes will present the award address before the Division of Fluorine Chemistry.

Advertisement

Article:

This article has been sent to the following recipient:

0 /1 FREE ARTICLES LEFT THIS MONTH Remaining
Chemistry matters. Join us to get the news you need.