January 13, 2003
Volume 81, Number 2
CENEAR 81 02 pp. 44-50
ISSN 0009-2347


2003 ACS NATIONAL AWARD WINNERS
Recipients are honored for contributions of major significance to chemistry

Following is the second set of vignettes of recipients of awards administered by the American Chemical Society for 2003. C&EN will publish the vignettes of the remaining recipients in successive January and February issues. An article on Edwin J. Vandenberg, 2003 Priestley Medalist, is scheduled to appear in the March 24 issue of C&EN along with his award address.

ACS Award in Pure Chemistry


Sponsored by Alpha Chi Sigma Fraternity

"Excellent role model," "remarkable creativity," and a "headliner in the field" are but a few of the accolades bestowed upon
8102award_Buriak
Buriak
Jillian M. Buriak, 35, associate professor of chemistry at Purdue University. Clearly, this materials chemist has a bright and promising future.

Buriak began her trek in silicon surface chemistry under the tutelage of M. Reza Ghadiri, her postdoctoral adviser at Scripps Research Institute and a former Pure Chemistry Award recipient. Collaborating with Michael J. Sailor--a chemistry and biochemistry professor at the University of California, San Diego--on a project involving high-surface-area porous silicon convinced Buriak that there was a "gold mine of reactivity there on silicon and other semiconductor surfaces that had not been tapped by way of catalysis and other wet chemical approaches."

Buriak developed a new and general chemistry that enables the functionalization of porous silicon surfaces with alkenes and alkynes. A photochemical hydrosilylation approach for elaborating the chemistry of these surfaces has also been achieved. A salient feature of these reactions is the stabilization of porous silicon nanocrystallites in which samples prepared by her method are stable for hours--as opposed to the usual seconds--upon exposure to basic solutions. Porous silicon functionalization approaches developed by the Buriak lab include Lewis acid mediat

ed, white-light induced, electrografting, and hydride abstraction initiated.

Buriak "has made tremendous strides in the areas of semiconductor and organo-metallic surface chemistry," a colleague notes. A hallmark of her research addresses the question as to whether a surface reacts like a molecule. By answering this, technologies to interface molecular electronics with silicon integrated circuits are becoming more viable.

The success of Buriak's research ostensibly may be attributed to her integrating two disparate chemical fields: organometallic catalysis and materials, which, as a colleague notes, "she has shaped into a field clearly her own." And while her approach to research is fundamental, it has important technological impacts and has proven to be highly versatile.

The stable surfaces effected through her research are used in biosensor, chemical sensor, and biomedical implant studies. She has extended her work on porous silicon chemistry by developing modified materials as matrices for matrix-assisted laser desorption/ionization mass spectroscopy. Additional applications for porous silicon include use in optoelectronic devices and photodetectors, and as a matrix for photopumped tunable lasers.

Buriak was born in Toronto. She earned a B.A. in chemistry from Harvard University in 1990 and a Ph.D. in organo-metallic chemistry from Université Louis Pasteur, Strasbourg, France, in 1995. Following a two-year postdoc with Ghadiri at Scripps, Buriak joined the Purdue University chemistry department as assistant professor in 1997. She became an associate professor in 2001.

Among her many awards are the Camille & Henry Dreyfus Foundation New Faculty Award (1997-2002), a School of Science Outstanding Undergraduate Teaching Award (2000), an Alfred P. Sloan Foundation Fellowship (2000-02), and a Cottrell Teacher-Scholar Fellowship (2000-02).

ACS Award in Inorganic Chemistry


Sponsored by Aldrich Chemical Co.

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Christe
Shake Karl O. Christe's hand, and you'll find he has a very strong grip. His grip on inorganic chemistry is equally strong. In fact, he is considered by many of his peers to be one of the preeminent main-group inorganic chemists in the world.

Christe, 66, "is an unusually creative, imaginative, and highly skilled chemist who not only has successfully tackled some of the most difficult and challenging synthesis problems in inorganic chemistry" but also has advanced our fundamental understanding of inorganic chemistry, writes a colleague. "This is highly unusual for a chemist who has spent a large part of his career in industry."

Born in Germany, Christe obtained a B.Sc., an M.Sc., and a Ph.D. from the Technical University in Stuttgart. He came to the U.S. in 1962 and launched his career at the Stauffer Western Research Laboratory in Richmond, Calif. After five years there, he moved to Rocketdyne in Canoga Park, Calif., where he worked from 1967 to 1994. Since 1994, Christe has held a joint appointment as a group leader at the Air Force Research Laboratory at Edwards Air Force Base and as a research professor at Loker Hydrocarbon Research Institute of the University of Southern California.

The chemical synthesis of elemental fluorine is just one of several accomplishments of Christe's that other chemists did not think were possible.

He also was the first to synthesize and characterize NF4+ salts such as NF4+XeF72. This particular salt is remarkable in that it contains more usable fluorine per volume than liquid fluorine itself!

One of Christe's major discoveries is the synthesis of truly anhydrous tetramethylammonium fluoride, which is often referred to as "naked fluoride" or the "Christe reagent." It provided a highly soluble fluoride ion source in combination with a chemically inert counterion that has allowed chemists to prepare a variety of unprecedented simple anions with coordination numbers in excess of six. Examples prepared by his group include IF5O22, TeF6O22, IF5O222 , and SbF722.

Another Christe coup was his discovery of the XeF52 anion--the first pentagonal planar AX5-type species ever prepared. Today, only two such anions are known, and the second one--IF522--also came out of Christe's lab.

Furthermore, Christe has synthesized and characterized an impressive number of new halogen-containing species such as ClF3O2, ClF4+, ClF62, BrF4+, and ClF4O2.

He and his coworkers also have made major advances in the field of thermally unstable or shock-sensitive compounds, such as covalent perchlorates and azides. They have synthesized and characterized highly energetic compounds such as ClOClO3, I(OClO3)3, CF3OClO3, CF3N3, C(N3)3+ClO42, and C(N3)3+N(NO2)22. Perhaps his most spectacular achievement was the synthesis of the N5+ cation and isolation of its thermally stable salts.

With David A. Dixon of Pacific Northwest National Laboratory (see page 47), Christe has developed a quantitative scale for fluoride ion affinities. This scale allows chemists to predict the stability of potential anions and serves as an ideal measure for Lewis acidities. Christe and Dixon also have developed the first quantitative scale for oxidizer strength.

A recent breakthrough from his lab has been the discovery of an improved process for generating singlet delta oxygen, which is important for a laser system that is the cornerstone of antimissile defense systems.

Christe's previous honors include the 1969 Apollo Achievement Award from the National Aeronautics & Space Administration, the 1986 ACS Award for Creative Work in Fluorine Chemistry, and the 2000 Prix Moissan.

The award address will be presented before the Division of Inorganic Chemistry.--RON DAGANI

ACS Award for Research at an Undergraduate Institution


Sponsored by Research Corporation

 
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Christensen
PHOTO BY DEAN ABRAMSON
Chemistry students who want to do research with Ronald L. Christensen at Bowdoin College in Brunswick, Maine, should review a short glossary of terms: conjugated p-electrons, fluorescence, nonradiative decay, and energy transfer. Their next step would be to write home and tell mom and dad that they won't be coming home over summer vacation.

Christensen, 57, the James Stacy Coles Professor of Natural Sciences, involves undergraduates in his research partly because of his own start in science at Oberlin College. The opportunity to do research during his first summer at Oberlin "opened a whole new world" to him and had a large impact on his choice of career.

As a graduate student at Harvard University under Bryan Kohler, Christensen encountered linear polyenes while doing his Ph.D. research on the chemistry of vision, involving the polyene vitamin A. His team studied the ordering of polyene electronic states and the disposition of the excitation energy and found that the lowest excited singlet state is totally symmetric, making absorption from the ground state strongly forbidden. According to a colleague, this discovery has had "a profound effect" on the study of the photochemistry of vision and the photochemical behavior of carotenoids and xanthophylls in photosynthetic organisms.

Christensen's graduate work sparked his interest in related areas of photobiology--or, as he describes it, "trying to understand what light does in biological systems where polyenes play important roles across the board," including photosynthesis, photoregulation, and circadian rhythms. As a physical chemist, he focuses on basic issues of electronic structure, specifically the low-temperature optical spectroscopy of linear polyenes and the characterization of the electronic and vibronic states of simple model systems and carotenoids.

As Christensen's interest in polyenes has grown, so has the size of the molecules he has studied. He gets students started in research at an early stage, synthesizing and then purifying long polyenes. This work sets the stage for later spectroscopic studies and understanding the physical principles involved.

Christensen's many publications on the electronic states of polyenes include numerous undergraduate coauthors. Because he attended an undergraduate college, he knows that "these schools have a significant impact on science due to the disproportionate number of students who continue in research" after graduation. Involving undergraduates in research has become an integral part of teaching science at Bowdoin.

Christensen has looked beyond Bowdoin for additional research experiences. During sabbaticals, he did time-resolved spectroscopy with David Phillips at the Royal Institution of Great Britain and high-resolution vibronic spectroscopy of polyenes in supersonic jets with Keitaro Yoshihara and Hrvoje Petek at the Institute for Molecular Science in Japan and with David Pratt at the University of Pittsburgh. A current project on the optical spectroscopy and excited-state dynamics of "infinite" polyenes (conjugated polymers) involves a collaboration with Richard Schrock at Massachusetts Institute of Technology; Ifor Samuel at the University of St. Andrews, in Scotland; and Tomas Polivka at Lund University, in Sweden.

Teaching undergraduates is paramount at Bowdoin College, and Christensen has found that doing research is a good way to teach. "In the end you have to be equally excited about the science and the education of your students."

The award address will be presented before the Division of Physical Chemistry.--MELODY VOITH

 

ACS Award in the Chemistry of Materials


Sponsored by DuPont

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Dalton
Larry R. Dalton, 59, loves to teach freshman chemistry. "It is where we derive our fundamental understanding of the chemical world," says the Harold E. & Lillian M. Moulton Professor of Chemistry and professor of materials science at the University of Southern California (USC) and the University of Washington, Seattle. As he lists freshman chemistry concepts, he slips naturally into what he himself continues to learn, revealing his deep-rooted interest in the fundamental characteristics and interactions of molecules.

Dalton's contributions to materials chemistry range from advances in theory to improved processing techniques to the synthesis of a new generation of electro-optic materials for telecommunications. His understanding and manipulation of electro-optic chromophores--organic polymers that convert electrical signals into optical ones--highlight his ability to step between wide-ranging disciplines: electrical engineering, physics, chemical engineering, organic chemistry, and materials science.

Dalton graduated from Michigan State University (MSU) in 1965 with a B.S. in mathematics and chemistry. He went on to earn an M.S. from MSU and a Ph.D. from Harvard University, both in chemistry. He began his teaching career at Vanderbilt University in 1971, and at the same time accepted a consultantship at Varian Analytical Instrument Division. It was during this period that he developed a theory of time- and frequency-resolved magnetic resonance, which led to new magnetic resonance techniques. He eventually applied these advances to help elucidate problems ranging from DNA dynamics and red blood cell protein interactions to characterizing the soliton wave function in polyacetylene.

In 1976, Dalton moved to the chemistry faculty at the State University of New York, Stony Brook, and while there, he consulted for Bruker Instruments and IBM. Because of his work on sickle cell hemoglobin aggregation, he was selected to participate in the National Institutes of Health Think Tank on Sickle Cell Anemia and later served for more than a decade as a member of the Parent Committee for the Review of the National Sickle Cell Program at NIH.

In 1982, Dalton moved to USC. There he began the study and synthesis of electroactive materials for optical applications and developed a new theoretical approach for treating long-range and spatially anisotropic intermolecular electrostatic interactions.

According to George Olah, 1994 Nobel Laureate in Chemistry and a colleague of Dalton's at USC, "This theoretical work has revolutionized the field of second-order nonlinear optical materials, permitting materials to be designed that exhibit electro-optic activities in excess of 100 pm per V." Subsequently, with what Olah dubs as "synthetic genius," Dalton synthesized stable, efficient chromophores and cladding materials, creating commercially viable families of electro-optic materials.

Dalton's theoretical and synthetic advances affect applications as diverse as phased array radar, cable television, optical gyroscopes, and computer data processing. "A strong argument can be made that he is one of the most creative pioneers of diverse aspects of nanoscale and supramolecular materials chemistry," Olah says.

Dalton is also a pioneer in education. He introduced materials science into his courses and initiated computer-assisted learning. In 2000, he received the Washington Institute for Teaching Excellence's Award for "Well Reasoned and Compelling Lectures."

The award address will be presented before the Division of Polymeric Materials: Science & Engineering.--LOUISA DALTON

ACS Award for Creative Work in Synthetic Organic Chemistry


Sponsored by Aldrich Chemical Co.

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Denmark
PHOTO BY THOMPSON MCCLELLAN
Scott E. Denmark has developed practical synthetic methods through careful mechanistic analysis and thorough understanding of reactivity. For this, the 49-year-old Reynold C. Fuson Professor of Chemistry at the University of Illinois, Urbana-Champaign, is being honored for creativity in synthetic organic chemistry.

Denmark is well known for devising a tandem [4 + 2]/[3 + 2] cycloaddition of nitroalkenes. The reaction leads to facile formation of nitrogen-containing polycylic compounds with great structural diversity from simple olefinic precursors in high yield. He has prepared numerous pyrrolizidene and indolizidene families in enantiomerically pure form by this approach.

Two of Denmark's most exciting recent contributions involve the chemistry of organosilanes. Although organosilicon reagents have been used extensively in organic synthesis, Denmark has identified a new opportunity for catalysis of organic reactions through use of chiral Lewis bases in combination with special types of silicon compounds.

One of the most successful demonstrations of this concept is Lewis-base-catalyzed asymmetric aldol addition. The creation of this reaction required a new class of reagents (trichlorosilyl enolates) and strongly donating catalysts such as chiral phosphoramides. With these, aldol additions of esters and ketones proceed with high yields, excellent and predictable diastereoselectivity, and high enantioselectivity. The Denmark lab has extended the concept of Lewis base activation to enantioselective allylation and propargylation of aldehydes and to additions of simple silyl ketene acetals and enol ethers to aldehydes.

In a second program that also features the special properties of organosilanes, Denmark developed a new class of palladium-catalyzed cross-coupling reactions that, according to a colleague, "promises to supplant the powerful Stille and Suzuki couplings, which require toxic tin or sluggish boron reagents." Initially using silacyclobutanes as the nucleophilic coupling partner, Denmark found through mechanistic studies that the ease with which the reaction occurs is due to in situ formation of silanols. Thus, in the presence of fluoride ion activators, other silicon derivatives--including silyl hydrides, silyl ethers, and disiloxanes--are productive coupling partners under mild conditions.

Detailed mechanistic studies showed that a silicon-oxygen-palladium interaction is key in the reaction. Thus, Denmark surmised that simple deprotonation of the silanol would lead to coupling. This insight led to a fluoride-free cross-coupling of organosilanols, an advance that, the colleague says, "will have an enormous impact on the use of this reaction in complex-molecule synthesis wherein silicon protective groups preclude use of fluoride activation."

"I can think of no one who has better married the goals of physical organic chemistry and synthesis," another colleague says. Denmark "is an exceptional mechanistic chemist who has used his skills to enable new ways of thinking about synthetic problems. He is unquestionably one of the thought leaders in the field."

Denmark completed an S.B. degree in 1975 at Massachusetts Institute of Technology. Guided by Albert Eschenmoser (see page 48), Denmark received a Ph.D. in 1980 from the Swiss Federal Institute of Technology (ETH), Zurich. He joined Illinois after his doctoral studies, becoming full professor in 1987 and Reynold C. Fuson Professor in 1991. His awards include the Alexander Von Humboldt Senior Scientist Award, an ACS Arthur C. Cope Scholar Award, and the Stuart Pharmaceuticals Award in Chemistry.

The award address will be presented before the Division of Organic Chemistry.--MAUREEN ROUHI

 

ACS Award for Creative Work in Fluorine Chemistry


Sponsored by Clariant LSM (Florida) Inc.

8102award_Dixon
Dixon
COURTESY OF PNNL
David A. Dixon may have made his greatest contribution in the field of computational chemistry. Dixon, 53, began work developing computational models for fluorinated systems in the early 1980s at DuPont, and remains focused on computational fluorine chemistry in his current position of Battelle Fellow at Pacific Northwest National Laboratory (PNNL).

Perhaps most notable among Dixon's accomplishments is his work on predicting the behavior and molecular properties of chlorofluorocarbon (CFC) alternatives. This proved critically important to all subsequent research in CFC replacement technologies--as well as to business development at DuPont--and a major win for chemistry in the effort to minimize stratospheric ozone depletion. Dixon's big breakthrough, however, was the introduction of computational science to fluorine chemistry, where chronic problems with calculating the behavior of molecules had restricted chemists' understanding of an important class of compounds.

Dixon, who received a Ph.D. in physical chemistry from Harvard University in 1975, tuned his penchant for computation on fluorine chemistry at DuPont, where he began working under research manager Bruce Smart in 1983. "There was a lot of free computer time around Christmas," Dixon says, so he hopped on to investigate the properties of CFCs and their alternatives.

This overtime dabbling paid off, Smart says. "There was no computational theory on the structure, bonding, or reactivity of fluorocarbons at that time, and we had little reliable thermochemical data," Smart says. "We turned David in that direction and, frankly, he was a smashing success." Using thermodynamic and kinetic parameters calculated from his work, Dixon and other DuPont staff were able to correctly predict the behavior of a pilot plant for production of CFC alternatives before the plant began operating.

Dixon's work has branched off in several directions. With Karl O. Christe, a researcher at the University of Southern California (see page 44), Dixon developed the first thermodynamic scale for predicting the oxidative power of oxidative fluorinators, important reagents for the design and synthesis of highly energetic materials. He and Christe are continuing to develop a general Lewis acidity scale based on fluoride affinities. Dixon and DuPont colleague A. J. Arduengo III discovered a totally new inversion process, edge inversion, based on computational results on trivalent main-group fluorides, and Dixon's calculations are credited with solving the 50-year-old problem of developing a complete analysis of the vibrational spectra of iodine heptafluoride.

At PNNL, Dixon has been developing a method based on very high level quantum chemical calculations for the reliable prediction of the heat of formation of fluorinated compounds from first principles. He has also calculated the properties of the fluorides and oxofluorides of the actinides, initially those of uranium, that are important in the processing of nuclear fuel and waste.

Dixon's computational work has led to major advances in his area of specialization, fluorine chemistry. But his work has had a wider impact on the way computational chemistry is used in industry, influencing the development of methods of predicting molecular properties at most major chemical companies. Christe has described Dixon as a chemist of the 21st century who transcends the traditional chemist's role of inventing new compounds or processes. Dixon, Christe says, has shed light on methods for problem solving across the entire spectrum of chemistry through the exploitation of computational chemistry.

The award will be presented during the 16th Winter Fluorine Conference, Jan. 12-17, in St. Pete Beach, Fla.--RICK MULLIN

 

ACS Award for Distinguished Service in the Advancement of Inorganic Chemistry


Sponsored by Strem Chemicals Inc.

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Eisenberg
PHOTO BY MARCIA EISENBERG
Knowledge, service, and promoting the field of inorganic chemistry have been the hallmarks of the career of chemistry professor Richard Eisenberg
of the University of Rochester. The research community's trust in Eisenberg's abilities was emphasized in January 2001 when he was named editor-in-chief of Inorganic Chemistry. That recognition has now been amplified by his being honored with this distinguished service award.

Among Eisenberg's career service contributions, he has served as chair of ACS's Inorganic Division (1993), chair of the division's Organometallic Subdivision (1982), and as ACS councilor for the division (1988-91). Eisenberg also served as chairman of the 1988 Gordon Conference on Organometallic Chemistry and was the founding organizer of the National Science Foundation Workshop on Organometallic Chemistry in 1977.

Much of Eisenberg's service has been carried out while he concurrently served as an associate dean of the Rochester College of Arts & Sciences (1989-91) or as chairman of the chemistry department (1991-94)--all in addition to pursuing an active research program.

Eisenberg's recent research has focused on the challenging subjects of catalysis and solar energy conversion, concentrating mainly on complexes of platinum, iridium, and rhodium. His group has shown over the years that the excited-state luminescence properties of these compounds can be tuned by systematic variation of the ligands. These properties are leading to potential applications in organic light-emitting diode technology for use in flat-panel displays, artificial photosynthesis to convert light to chemical energy, and as chemical sensors.

Part of his work involved the synthesis and study of the first members of the binuclear class of transition-metal compounds called A-frames. These systems with bridging ligands have been shown to have flexible structures capable of reacting with substrates in different ways. For example, carbonylation studies of rhodium alkyl A-frame complexes led to the discovery of one of the few cases of binuclear catalysis where both metal centers are required to effect transformations.

Studies on the catalytic properties of these binuclear complexes resulted in Eisenberg's group being one of the first to observe parahydrogen-induced polarization. This nuclear magnetic resonance effect, in which H2 is primarily in the para spin state, allows small concentrations of species such as catalyst intermediates to be observed directly. This finding provided proof that catalytic hydrogenation mechanisms involve transfer of molecular hydrogen.

Earlier in his career, Eisenberg carried out seminal studies on complexes of dithiolate ligands, reduction of nitric oxide by carbon monoxide, water gas shift reactions, indirect electroreduction of CO2, and photochemical carbonylation of C–H bonds.

Education has also been a focus for Eisenberg. Along with Rochester chemistry professor James M. Farrar, he has developed a first-year chemistry curriculum taught in the context of "energy and the environment." Another project centers on using an online newsgroup as a tool for students to help each other learn.

Eisenberg, 59, was born in New York City and attended Columbia University for his undergraduate and graduate chemistry studies. He earned an A.B. in 1963, an M.A. in 1964, and a Ph.D. in the group of professor Harry B. Gray in 1967. He began his teaching career at Brown University, moving to Rochester in 1973.

The award address will be presented before the Division of Inorganic Chemistry.--STEVE RITTER

Roger Adams Award in Organic Chemistry


Sponsored by Organic Reactions Inc. and
Organic Syntheses Inc.

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Eschenmoser
Considered one of the giants of 20th-century organic chemistry, Albert J. Eschenmoser is this year's recipient of the Roger Adams Award in Organic Chemistry. Summarizing his achievements is an impossible task because, as one colleague puts it, his "contributions to organic chemistry are so many, and they have all been on the frontier of our science."

Eschenmoser, 77, is a professor emeritus at the Swiss Federal Institute of Technology, Zurich (ETH), and a professsor at Scripps Research Institute. His first major accomplishment, chronicled in his Ph.D. thesis, was the use of carbonium ion chemistry to explain the biosynthesis and structures of cyclic terpenes. This advance in the understanding of terpenoid biosynthesis subsequently made it possible for Leopold Ruzicka, his Ph.D. mentor, to formulate the biogenetic isoprene rules. These famous rules rationalize how cyclic terpenes and steroids are derived from noncyclic precursors by cyclizations and rearrangements.

Eschenmoser is perhaps best known for his work in organic synthesis. The total synthesis of vitamin B-12, which he achieved in collaboration with Harvard University's Robert B. Woodward, is considered one of the most ambitious total syntheses ever undertaken. Powerful synthetic methods he developed include the Eschenmoser fragmention, the Eschenmoser versions of the Claisen rearrangement and the Mannich reaction, the sulfide contraction to convert an amide into a vinylogous amide, and the Eschenmoser a-chloronitrone/olefin cycloaddition.

However, Eschenmoser's crowning achievement may be his more recent work on the origin of life. His systematic investigations of potentially natural nucleic acid alternatives have shown that Watson-Crick pairing is not a specific property of the ribofuranosyl system and that nature did not select RNA according to the criterion of maximization of base-pairing strength. His studies of pyranose RNA have provided evidence for the mode in which the specific nature of the sugar governs the pairing behavior of oligonucleotides.

As a colleague puts it: "Eschenmoser's work is marked by a uniquely deep understanding of chemical reactivity, which becomes evident in every discussion with him, from which his colleagues leave again and again with feelings of admiration, enlightenment, modesty, and, yes, inferiority."

ETH may rightly claim to be Eschenmoser's second home. There, Eschenmoser received diploma and Ph.D. degrees in 1949 and 1951, respectively. He became a privatdozent for organic chemistry in 1956 and a full professor in 1965. He retired officially in 1992 but continues to be active at both ETH and Scripps.

Eschenmoser has received eight honorary doctorates from U.S. and European institutions. He is a foreign associate of the National Academy of Sciences, a foreign member of the Royal Society, and an honorary foreign member of the American Academy of Arts & Sciences. His numerous awards include the Grande Médaille d'or de l'Académie des Sciences, from Institut de France, Paris; the Nakanishi Prize, from the Chemical Society of Japan; the Wolf Prize in Chemistry; the ACS Arthur C. Cope Award; and the Tetrahedron Prize for Creativity in Organic Chemistry.

The Roger Adams Award will be presented to Eschenmoser in March at the ACS national meeting in New Orleans. However, Eschenmoser will deliver his award lecture in June at the National Organic Chemistry Symposium, which will be held at Indiana University, Bloomington.--MAUREEN ROUHI

 

James Bryant Conant Award in High School Chemistry Teaching


Sponsored by Albemarle Corp.

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Ford
LIFETOUCH NATIONAL SCHOOL STUDIO PHOTO
The chance to participate in one of Linda K. Ford's classes could easily be one of the hottest tickets in any city. This year's recipient of the high school teaching award, Ford makes the subject of chemistry fascinating, captivating, and thrilling.

Ford puts on a Brazilian dress and dances to the song Mambo Italiano as she combusts a methane soap bubble column. She dresses as the Great Chemtini for Halloween before performing chemical "magic" tricks that she then explains. She has her class sing, eat cake, and chew vitamin C on Feb. 28 for the birthday of her hero, Chemistry Nobel Laureate Linus Pauling.

She is thorough and demanding. When they write or make presentations, her students must be clear and articulate. They complete between 32 and 34 experiments per year in a lab that is well equipped as a result of her grant applications. One assignment is to design an experiment that studies the kinetics of reactions involving calcium carbonate-hydrochloric acid.

Born in 1948, Ford has been teaching since 1971, after she obtained a B.A. in chemistry from Ohio Wesleyan University and an M.A. in teaching from the University of Chicago. She first taught chemistry for two years at a Chicago high school before returning to her hometown of Cincinnati in 1973 to teach chemistry and physics at Robert A. Taft High School, in one of Cincinnati's poorest neighborhoods. There, she gained the support of General Electric Jet Engine to launch a science fair, in which 40 GE engineers assisted 200 students.

She left Taft High School after a year to teach at Sycamore High School, where she stayed until 1978. There, she implemented a new curriculum, still used today, for the lowest track students. In 1979, she became a night school instructor at Cincinnati State Technical College to have more time to raise her three children. She revamped the college's lab component of the basic chemistry course to make it more quantitative.

She returned to Sycamore in 1985 to teach chemistry and physics. The school's environmental club, where she was the adviser, launched the community's first recycling program in 1986. It was later taken over by the local government, which awarded civic commendations to the students for their contributions to improving the environment through recycling.

Ford says that her participation in a three-week trip to Japan after she won a Fulbright award in 1998 was "life-altering." She says she was "overwhelmed" by the energy, creativity, and dedication to learning she felt as part of a group of 200 teachers and that she came back with "an arsenal of neat ideas." She has since set up direct educational exchanges with students and teachers in Japan.

She has been teaching chemistry at Seven Hills High School since 1999. Former School Head Susan Marrs says that Ford has "single-handedly turned our Science Club into a wildly popular (and still educational) student activity that features kids presenting to other kids." Her students made live presentations at public libraries during National Chemistry Week, Marrs adds.

Ford networks extensively. She gives advice and information to younger teachers. She is active in Cincinnati's Educators' Discussion Group and the ACS local section. She received a central regional award in high school chemistry teaching from ACS in 2000. The Cincinnati Section of ACS reports that it received 17 letters of support for Ford, even though only five were needed.

The award address will be presented before the Division of Chemical Education.--JEAN-FRANÇOIS TREMBLAY

 

Ralph F. Hirschmann Award in Peptide Chemistry


Sponsored by Merck Research Laboratories

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Freidinger
When Roger M. Freidinger, 55, was a young boy growing up in a small farming community outside of Peoria, Ill., he assumed he'd end up working on the family farm.

Then his parents gave the barely teenage Freidinger--now executive director of medicinal chemistry at Merck--a chemistry set. He promptly converted a table in his parents' basement into a makeshift laboratory and has been at it ever since. After receiving a B.S. in chemistry from the University of Illinois, Urbana-Champaign, in 1969, Freidinger left his home state for Massachusetts Institute of Technology, where he completed a Ph.D. in organic chemistry under the guidance of professor George Büchi in 1975.

That same year, peptide chemist Ralph F. Hirschmann recruited Freidinger to Merck, where he has remained to this day. Freidinger's career at Merck "is characterized by its significance, by its seminal nature, and the sophistication of its execution," says Hirschmann, who is now a professor of bioorganic chemistry at the University of Pennsylvania.

Freidinger has spent his career searching for therapeutically useful peptides, peptidomimetics, and other small molecules designed to bind peptide receptors. Along the way, he has created a number of invaluable tools for peptide chemists, including methodology for the synthesis of amino acids and cyclic peptides.

Using computer-based molecular modeling, a technique which at the time was still in its infancy, Freidinger designed what now are widely known as "Freidinger lactams"--dipeptide lactams that are used to make floppy peptides more rigid. Such rigidity can be crucial to ensuring that a peptide therapeutic lasts long enough in the body to do some good.

He used his lactam to create synthetic analogs of a peptide called luteinizing hormone-releasing hormone that controls levels of sex hormones in the body. Analogs of LHRH are used to treat breast and prostate cancers. In Freidinger's version, the conformational constraint afforded by the lactam mimicked the beta turn of endogenous LHRH bound to its receptor, yielding a more potent LHRH analog.

Freidinger also played a significant role in Merck's development of synthetic analogs of somatostatin, an endogenous 14-amino acid peptide that acts as a neurotransmitter as well as an inhibitor of hormone secretion. Using the bioactive conformation of somatostatin as a guide, he designed a potent cyclic hexapeptide analog--a breakthrough that showed chemists how to use rational design to increase the metabolic stability of peptides. Freidinger's subsequent investigation of the relationship among structure, conformation, and activity showed that somatostatin's amide backbone isn't crucial to its activity. This opened the door for the design of active peptidomimetics lacking an amide backbone.

More recently, Freidinger has turned his attention to improving doxorubicin, a potent, broad-spectrum antitumor agent. In order to selectively kill prostate tumor cells, he and his coworkers have designed and synthesized an inactive peptide-doxorubicin conjugate that is converted to active doxorubicin by a prostate-specific protease. This approach has now been extended to the antitumor agent vinblastine.

Freidinger is a fellow of the American Association for the Advancement of Science. He has served on National Institutes of Health study sections and the panel that awards National Science Foundation graduate fellowships. He is currently president-elect of the American Peptide Society.

The award address will be presented before the Division of Medicinal Chemistry.--AMANDA YARNELL

 

E. B. Hershberg Award for Important Discoveries in Medicinally Active Substances


Sponsored by Schering-Plough Research Institute

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Ganguly
In the increasingly compartmentalized pharmaceutical industry, Ashit K. Ganguly has accomplished something rare: success in both the scientific and management realms.

During a 30-year career with Schering-Plough, Ganguly discovered or was involved in the discovery of several important medicinal compounds, including the company's recently approved cholesterol-lowering drug Zetia. He has published some 160 research papers and holds more than 90 U.S. patents.

At the same time, Ganguly rose through the managerial ranks at Schering-Plough Research Institute to become senior vice president of chemical research, responsible for more than 250 scientists at the company's Kenilworth, N.J., research complex. He retired from this position in 1999 and is now, at age 68, Distinguished Research Professor of Chemistry at Stevens Institute of Technology, Hoboken, N.J.

Born in India, Ganguly earned a B.Sc. in chemistry from Delhi University and stayed on for a Ph.D. in organic chemistry with T. R. Seshadri in 1959. Ganguly then went to Imperial College, London, as an 1851 Exhibition Scholar and received a second Ph.D. in 1962 under the supervision of Sir Derek H. R. Barton, whom Ganguly calls the greatest influence in his scientific career.

After stints at Western drug company labs in India and at the Research Institute for Medicine & Chemistry in Cambridge, Mass., Ganguly joined Schering-Plough in 1968. His early work at the company focused on the discovery of new antibiotics, notably Ziracin, a complex natural-source oligosaccharide.

Ganguly elucidated Ziracin's structure by degrading it to smaller units, determining their structures, and then reconstituting the molecule again. The structure was later confirmed with its first total synthesis by K. C. Nicolau of Scripps Research Institute, who remarked during a lecture at an ACS meeting that the structural assignment made by Ganguly and colleagues was entirely correct.

Former Schering-Plough Research Institute colleagues give Ganguly high marks for his work on Sarasar, a farnesyl protein transferase inhibitor, now in clinical trials, that represents a new class of noncytotoxic anticancer agents. John J. Piwinski, the firm's current head of chemical research, says the program owes its success largely to Ganguly's integration of medicinal chemistry with several new technologies, including X-ray crystallography, spectroscopy, molecular modeling, and combinatorial chemistry.

Another drug developed under Ganguly's guidance is posaconazole, an antifungal now in Phase III clinical trials for the treatment of serious fungal infections such as those that afflict AIDS and cancer patients. He was also instrumental in the discovery of Zetia, which takes a new approach to cholesterol reduction. Most cholesterol-reducing drugs work by blocking production of cholesterol in the liver; Zetia complements them by blocking the uptake of dietary cholesterol.

As a leader, Piwinski says, Ganguly always took time to visit laboratories and talk to the scientists working on the company's programs. Ganguly acknowledges that this was a conscious effort on his part. "I strongly believe you cannot manage scientists at a pharmaceutical company unless you do science yourself," he says.

Although Ganguly worked in chemical research, he notes that Schering-Plough drug discovery projects increasingly depend on scientists from other disciplines such as biology and drug metabolism. Ganguly says he accepts the award on behalf of "all the colleagues that I worked with for many years, without which this would not be possible."

The award address will be presented before the Division of Medicinal Chemistry.--MICHAEL MCCOY



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