AWA R DS ACS NATION A L AWA RDS W INNERS
2012 ACS NATIONAL AWARD WINNERS Recipients are HONORED FOR CONTRIBUTIONS of major significance to chemistry EDITED BY SOPHIE L. ROVNER
vignettes of recipients of awards administered by the American Chemical Society for 2012. C&EN will publish the vignettes of the remaining recipients in January and February issues. A profile of Robert S. Langer, the 2012 Priestley Medalist, is scheduled to appear in the March 26 issue of C&EN along with his award address. Most of the award recipients will be honored at an awards ceremony that will be held on Tuesday, March 27, in conjunction with the spring ACS national meeting in San Diego. However, the Arthur C. Cope Scholar awardees will be honored at the fall ACS national meeting in Philadelphia, Aug. 19–23.
ALFRED BURGER AWARD IN MEDICINAL CHEMISTRY Sponsored by GlaxoSmithKline Best known for his work in developing a diagnostic agent for Parkinson’s disease and treatments for cocaine and nicotine addictions, F. Ivy Carroll is being honored for his numerous contributions to drug discovery and development over his more than 50-year career. Carroll, 76, joined Research Triangle Institute (RTI) International in 1960 as an organic chemist and has been working there ever since. Currently, he serves as a distinguished fellow in medicinal chemistry. A major part of Carroll’s research has been the synthesis and pharmacological characterization of 3-phenyltropane analogs. That work led to the development of RTI-55, better known as Dopascan, an imaging agent used to diagnose Parkinson’s. The 3-phenyltropane Carroll
research also led to the development of potential therapies for cocaine addiction, including the dopamine transporter selective inhibitor RTI-336. The compound has progressed through Phase I clinical trials, and Carroll hopes the National Institutes of Health will continue clinical development. More recently, Carroll has been studying opioid receptors—work that has led him to identify the Κ-opioid receptor antagonist JDTic. That compound is currently in Phase I clinical trials for the treatment of cocaine addiction. Carroll has also been investigating nicotinic receptors with hopes of finding more effective smoking cessation therapies. “JDTic attenuated the physical and affective nicotine withdrawal signs in mice,” he says. “JDTic also has antidepressant and anxiolytic activity in animal tests.” Philip S. Portoghese, a distinguished professor of medicinal chemistry at the University of Minnesota, Twin Cities, describes Carroll as “one of the foremost medicinal chemists in the U.S., if not the world.” He has “skillfully and creatively applied his outstanding knowledge of organic chemistry to the design and synthesis of selective ligands for use as tools in multiple areas that include drug abuse and radioimaging agents,” Portoghese says. Carroll is an internationally recognized medicinal chemist, says Scott P. Runyon, a research scientist at RTI International. “There is no doubt that his scientific contributions will continue to play a major role in advancing the understanding of the scientific basis of drug abuse and will lead to new medications for treatment of this illness.” After more than 50 years, Carroll continues to search for new therapies for drug addiction. “Having the opJ. W. C RAWFORD/RTI INTERNATIONAL
FOLLOWING IS THE FOURTH set of
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portunity to see eight compounds designed in my laboratory progress to human studies was exceptionally rewarding,” he says. “It is also very rewarding to know that my research and recognition from this award will bring more attention to the need for substance abuse treatments.” Carroll will present the award address before the ACS Division of Medicinal Chemistry.—BRITT ERICKSON
ACS AWARD FOR ENCOURAGING WOMEN INTO CAREERS IN THE CHEMICAL SCIENCES Sponsored by the Camille & Henry Dreyfus Foundation In some respects, Yves J. Chabal, Texas Instruments Distinguished University Chair in Nanoelectronics and professor and head of the materials science and engineering department at the University of Texas, Dallas, might seem an unlikely recipient for the ACS Award for Encouraging Women into Careers in the Chemical Sciences. Most notably, “he is trained as a physicist, not as a chemist; has spent most of his career outside academics, and therefore has mentored relatively few students; and is a man,” unlike the past recipients of the award, says Kate Queeney, associate professor of chemistry at Smith College, in Northampton, Mass., and a former Chabal mentee. Nevertheless, Chabal, 59, “has demonstrated unparalleled success both at mentoring women generally and at helping women to be placed in academic positions more specifically,” Queeney says. Throughout his career—which includes 22 years as a surface physics researcher at Bell Laboratories and five years as a professor of chemistry, chemical biology, and biomedical engineering and director of the Laboratory for Surface Modification at Rutgers University—Chabal has worked to achieve gender equality among the Ph.D. students and postdoctoral fellows in his research group, Queeney says. The same holds true now in his role at UT Dallas, which he joined in 2008. In addition, he has been dedicated to mentoring those in his group, consistently helping them meet their goals, “regardless of whether their goals align with his own,” she says. “From the time I was a postdoc in Yves’s group at Bell Labs in the early 1990s, he has been a tireless proponent of my academic
GEORGE A. OLAH AWARD IN HYDROCARBON OR PETROLEUM CHEMISTRY Sponsored by the George A. Olah Award Endowment In the field of biomass conversion, few researchers are better known or more highly respected than James A. Dumesic,
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selectively dehydrating fructose. He then followed that study with another showing that liquid fuels can be made from fructose in a biphasic reactor by way of a process that avoids the expensive separation steps typically needed to produce liquid fuels. In other examples of the Dumesic group’s biomass work, the team developed methods for making liquid alkanes from glycerol by way of a process involving catalytic conversion to synthesis gas (H2 and CO) and Fischer-Tropsch C–C coupling chemistry. They also engineered methods for catalytically converting sugars and polyols to various classes of hydrocarbons. For example, the method can be tuned to produce branched hydrocarbons and aromatic compounds used in gasoline, or less branched and longer-chain hydrocarbons of the type needed for diesel and jet fuels. Dumesic, 62, earned a bachelor’s degree in chemical engineering in 1971 from UW Madison and a Ph.D. in chemical engineering from Stanford University in 1974. After conducting research in France and Russia, he was appointed as an assistant professor of chemical engineering at UW Madison in 1976. Dumesic is a member of the National Academy of Engineering and has received numerous honors including the Heinz Heinemann Award in Catalyst Science & Technology of the International Association of Catalysis Societies and the ACS Gabor A. Somorjai Award for Creative Research in Catalysis. He has published more than 300 scholarly papers and holds 12 patents. Dumesic will present the award address before the ACS Division of Catalysis Science & Technology.—MITCH JACOBY SIKANDER HAKIM
the Steenbock Professor of Engineering and the Michel Boudart Professor of Chemical & Biological Engineering at the University of Wisconsin, Madison. The field’s objective can be stated simply: to transform biological materials—typically derived from plants—into valuable chemicals and fuels. Discovering the catalytic processes and reaction conditions needed to efficiently drive those chemical conversions, however, is enormously challenging. The biomass field has recently attracted many researchers. But according to catalysis experts such as University of California, Berkeley, chemical engineering professor Enrique Iglesia, Dumesic’s contributions are unparalleled. “Dumesic’s group has made the most significant conceptual and practical contributions to biomass conversion to fuels, chemicals, hydrogen, and synthesis gas,” Iglesia asserts. It is for these groundbreaking contributions that Dumesic is being honored. In some of Dumesic’s earliest work in this area, he and his group demonstrated that light alkanes and hyDumesic drogen could be produced from biomass-derived oxygenates including glucose, sorbitol, and glycerol via a process known as aqueous-phase reforming. The Wisconsin team also showed that by tailoring the reaction conditions, heavier alkanes—mainly butane, pentane, and hexane—could be produced from sorbitol. Moving toward higher-molecularweight products, Dumesic’s team developed C–C bond-forming methods for converting renewable sources, such as xylose and fructose, to liquid alkanes in the C7 to C15 range. The process includes acidcatalyzed dehydration followed by aldol condensation and involves a key intermediate: hydroxymethylfurfural (HMF). Recognizing that HMF is a versatile “platform” chemical—it can be used to synthesize solvents, fuels, and monomers for polymer production—Dumesic devised a high-yield method for producing HMF by COU RT ESY O F Y VES CHA BA L
aspirations,” says Melissa A. Hines, a professor and director of the Cornell Center for Materials Research at Cornell University. Initially, “he made it a priority to give me the exposure necessary to land a position in a topranked university,” she says. Chabal arranged for her to give multiple presentations at conferences and universities, for example. In 1993, when Hines was searching for a position amid Chabal a poor academic job market, Chabal wrote letters of recommendation to the 18 institutions to which she applied. In addition, he “worked the phones to help me get nine interviews and five offers,” she says, before she settled on Cornell, where Chabal earned a Ph.D. in physics in 1980. As Hines began her career, Chabal continued to work on her behalf, helping her gain exposure through lectures and media outlets, she says. “One of the most successful surface chemists of his generation,” Chabal has provided the same support to many other chemists, Hines says. “My experience has been by no means unique.” Throughout his career, Chabal says, he has been motivated to develop and nurture the best talent, irrespective of gender. “This has led me to have more women than men in my research group; indeed, women tend to behigherachieversbecausetheyhavehadto perform at a higher level to obtain the same recognition in scientific fields,” he adds. Despite these efforts, Chabal says, he feels “very humbled” by receiving this ACS award, which he sees as a “recognition that men can and must provide the same support and opportunities to women as they do to male scientists.” Chabal will present the award address before the ACS Women Chemists Committee.—SUSAN AINSWORTH
HERBERT C. BROWN AWARD FOR CREATIVE RESEARCH IN SYNTHETIC METHODS Sponsored by the Purdue Borane Research Fund and the Herbert C. Brown Award Endowment Jonathan A. Ellman’s development of
tert-butanesulfinamide as a versatile chiral
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ACS AWARD IN COLLOID & SURFACE CHEMISTRY Sponsored by Procter & Gamble For more than 25 years, Robert J. Hamers, the Wisconsin Distinguished Professor of Chemistry at the University of Wisconsin, Madison, has been discovering fundamen-
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tal phenomena in the surface chemistry of materials. Experts in surface chemistry hold Hamers in high esteem for the breadth of his scientific contributions, which often center on devising methods for functionalizing surfaces. John N. Russell Jr., head of surface chemistry at the Naval Research Laboratory in Washington, D.C., regards Hamers as “one of the premier surface chemists of his generation.” In recent years, Hamers’ research group has focused on sorting out mechanistic details of novel chemical and photochemical processes to control the surface chemistry and electronic properties of a variety of materials. Examples include layers of molecules adsorbed on diamond, carbon nanofibers, amorphous carbon, silicon, and metal oxides. In silicon surface chemistry, for example, Hamers’ team devised a direct method for covalently modifying silicon with DNA. That work led to the discovery that grafting molecular monolayers to diamond via photochemistry results in functionalized surfaces with exceptional chemical stability and chemical and biochemical specificity. A key piece of that discovery was recognizing that photoelectron emission was responsible for initiating the grafting process. Shortly thereafter, Hamers and coworkers showed that photochemical grafting of molecular layers can also be used to functionalize metal oxides and nanostructured carbon materials. Those advances touched off a major effort to exploit carbon and other materials as novel platforms for building biomolecular surface arrays. These arrays, in turn, have been incorporated into new types of chemical and biological sensors that directly convert molecular detection events into electrical signals. In related work, the Wisconsin researcher’s team made the first biologically sensitive field-effect transistors by using diamond thin films for real-time detection of antibody-antigen interactions. And in other work, Hamers’ team demonstrated that vertically aligned carbon nanofibers can be fashioned into yet another novel type of chemical sensor. The team showed that these nanofibers are a reactive form COURTESY OF ROBERT HAMERS
that is useful and finds application in industry is the ultimate reward in developing new methods.” As Ellman points out, tertbutanesulfinamide’s impact is illustrated by the more than 250 patents filed in the past three years by pharmaceutical, agrochemical, and other chemical companies using the reagent either for the discovery of new amine-containing compounds or production of chemicals for clinical trials. “The chemistry is reliable and it does have a broad scope,” Ellman says. “A lot of people in academe and in industry have developed very nice chemistry using this reagent.” In research that predates his work on tert-butanesulfinamide, Ellman was a pioneer in the development of combinatorial chemistry, which Carreira describes as “nothing less than a paradigm shift.” In more recent work independent of his studies on tert-butanesulfinamide, Ellman has collaborated with UC Berkeley chemistry professor Robert G. Bergman to develop catalytic C–H bond functionalization methods for efficient C–C bond formation. Ellman, 49, received a B.S. in chemistry in 1984 from Hamers Massachusetts Institute of Technology and a Ph.D. in chemistry in 1989 from Harvard University. After a postdoctoral fellowship at UC Berkeley, he joined the university’s faculty in 1992. He moved to Yale in 2010. He has received numerous fellowships and awards, including an Arthur C. Cope Scholar Award in 2000. Ellman will present the award address before the ACS Division of Organic Chemistry.—RUDY BAUM COU RT ESY O F JO N AT HAN EL L M A N
amine reagent for the asymmetric synthesis of amine-containing compounds tends to be discussed in superlatives. Ellman “has crafted, without question, one of the most useful auxiliaries,” says Erick M. Carreira of the Swiss Federal Institute of Technology, Zurich. “The derived tert-butylsulfinyl imines are the go-to intermediates for the synthesis of an incredibly wide range of amines.” “This chemistry has changed the ability of chemists to prepare chiral derivatives containing nitrogen,” says John F. Hartwig of Ellman the University of California, Berkeley. “I would place this method among the most practical and utilized of all methods reported in the past decade.” As Ellman, who is a chemistry professor at Yale University, points out, a large majority of drugs and drug candidates incorporate the amine functionality. Nevertheless, until his work with tert-butanesulfinamide beginning in the late 1990s, efficient methods for the asymmetric synthesis of many structural classes of amines weren’t available. Ellman and coworkers were the first to isolate enantiomerically pure tertbutanesulfinamide and perform its direct condensation with aldehydes and ketones to yield N-tert-butanesulfinyl imines. They further advanced a variety of nucleophilic additions to tert-butanesulfinyl imines for amine synthesis. He and his coworkers also developed a highly efficient method to prepare enantiomerically pure tert-butanesulfinamide by a two-step process of catalytic asymmetric oxidation of tert-butyl disulfide, which is an oil waste by-product and therefore an extremely inexpensive starting material. “We didn’t patent the reagent or its synthesis,” Ellman says. “Well over 100 companies now sell it.” Most of those companies produce the compound in up to 1-ton quantities using the synthetic route from tert-butyl disulfide developed by Ellman. “I was surprised I won the award and am really excited about it,” Ellman says. “What I really appreciate about it is that Brown developed very useful chemistry that’s seen application throughout the chemical industry. That’s something I always wanted to do. Introducing chemistry
ALFRED BADER AWARD IN BIOINORGANIC OR BIOORGANIC CHEMISTRY
Determined not to waste another year sitting in a science class learning nothing, Hoffman vowed to learn something in his chemistry class, regardless of the teacher. “I had a different charming rogue for a teacher, who taught us nothing, but this time I wasn’t going to be cheated so I worked really hard. Somehow that got me on the chemistry train, and I never got off,” he says. Hoffman went on to earn a B.S. from the University of Chicago in 1962 and a Ph.D. from California Institute of Technology with Harden M. McConnell in 1966, both Hoffman in chemistry. After a postdoctoral year at Massachusetts Institute of Technology with Alexander Rich, he joined Northwestern in 1967. In the decades that followed, Hoffman has become a pioneer in the field of bioinorganic chemistry. It is for his work using electron-nuclear double resonance (ENDOR) to study metalloenzymes that he is now being honored. “When I started using this tool, the technical problems of applying it to metalloenzymes hadn’t been solved,” Hoffman explains. “It wasn’t clear how you would systematically use this tool to understand enzyme structure and mechanism,” he notes, adding that today, researchers worldwide are involved in this area. The ENDOR work in Hoffman’s lab is currently focused on understanding numerous enzymes, particularly nitrogenase. In addition to the ENDOR studies, his lab also investigates electron transfer within protein complexes and the synthesis of novel porphyrazine macrocycles. He has
Sponsored by the Alfred R. Bader Fund Ask chemists how they got interested in chemistry and you often hear about how they played with chemistry kits or had an inspirational teacher. But for Brian M. Hoffman, chemistry professor at Northwestern University, the interest came as a result of an uninspiring high school physics class. “At my high school, you took physics as a junior and chemistry as a senior if you were interested in science,” Hoffman says. “I had a charming rogue of a teacher, who gave me a good grade, but at the end of the year I was chagrined to realize I hadn’t learned a bloody thing.” WWW.CEN-ONLIN E .ORG
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more than 540 publications to his credit. “Hoffman has made wide-ranging contributions to advancing the chemistry enterprise through his work in bioinorganic chemistry, in particular through his development of ENDOR spectroscopy as essential in the determination of metalloenzyme catalytic mechanisms,” says Joan S. Valentine, a chemistry professor at the University of California, Los Angeles. “His laboratory has been decisively involved with all the major metalloenzymes, including nitrogenase, cytochrome oxidase, hydrogenases, peroxidases, monoand dioxygenases, and FeS centers including ‘radical S-adenosylmethionine’ enzymes.” Hoffman has not only identified and characterized the structures of key intermediates, but he has also “devised and implemented novel kinetic methods of exploring their reactivity,” adds Judith P. Klinman, a chemistry professor at UC Berkeley. Hoffman has won numerous awards, including the Royal Society of Chemistry’s Bruker Prize in 1997, the Russian Academy of Sciences’ Zavoisky Prize in 2007, and the Max Planck Society’s Frontiers in Biological Chemistry Award in 2008. He is a fellow of the American Association for the Advancement of Science, the American Academy of Arts & Sciences, and the International Society of Magnetic Resonance and is also a member of the National Academy of Sciences. Hoffman will present the award address before the ACS Division of Inorganic Chemistry.—SUSAN MORRISSEY N O RT HWEST ER N U
of carbon endowed with unusual electrontransfer properties associated with exposed graphite edges along the nanofiber sidewalls. In the view of UW Madison chemistry professor John C. Wright, Hamers’ contributions to surface chemistry are especially valuable because his methods are general and applicable to many surfaces. They are also central to controlling chemical selectivity and other properties of materials used in fuel cells, energy storage devices, and biomaterial interfaces. “Hamers’ work moves surface chemistry from laboratory demonstration to practical applications,” Wright says. Hamers, 53, completed his undergraduate studies at UW Madison in 1980 and earned a Ph.D. in physical chemistry from Cornell University in 1986. He then became a research staff member at IBM’s T. J. Watson Research Center, in Yorktown Heights, N.Y., where he worked until taking a faculty position in the UW Madison chemistry department in 1990. Hamers has mentored more than 65 graduate students and postdoctoral researchers. He has authored some 250 papers in scholarly journals and holds 10 U.S. patents. He is a fellow of the American Association for the Advancement of Science and a recipient of the ACS Arthur W. Adamson Award for Distinguished Service in the Advancement of Surface Chemistry. Hamers will present the award address before the ACS Division of Colloid & Surface Chemistry.—MITCH JACOBY
