A BARELY CHIRAL MOLECULE, EXPOSED - C&EN Global

Apr 2, 2007 - Configuration study pushes Raman technique to its limits ... "Were he alive today, Lord Kelvin"—who introduced the concept of chiralit...
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ROUGH SEAS AHEAD ACS MEETING NEWS: Reports on U.S.

chemistry, chemical engineering warn or challenges, problems

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N THE NEXT DECADE, the U.S., a world leader in chemistry and chemical engineering, will remain strong in these disciplines, but challenges such as growing competition from Europe and Asia threaten to erode its lead. That's the conclusion of two National Research Council reports that were unveiled in preliminary fashion at last week's ACS national meeting in Chicago. The title of a presentation on the report "Benchmarking the Research Competitiveness of the U.S. in Chemistry" gave the forecast: "partly cloudy with a chance of showers." Or, as Charles P. Casey, a former president of ACS and chair of the panel that produced that report, put it, "Things are going well for chemistry" in the U.S., "but there are problems ahead." For example, U.S. leadership in generating the most highly cited chemistry papers is diminishing, and that trend will continue as other countries increase the number and quality of their papers. Another panel member—Sylvia T. Ceyer, a chem-

istry professor at MIT—noted that fewer and fewer U.S. students are getting doctorates in chemistry and the U.S. already depends critically on foreign-born graduate students and postdocs to carry out chemical research. As opportunities in other nations blossom, the U.S. may find it increasingly difficult to attract outstanding chemistry researchers from other countries. In addition, funding for chemical research has been struggling to keep up with inflation, Ceyer pointed out. That trend is projected to continue. Although the U.S. will hold on to its lead in chemistry for at least the next five years, she said, that lead will continue to shrink as competition heats up. A similar benchmarking assessment of chemical engineering research was carried out by a panel chaired by MIT chemical engineer George Stephanopoulos, who was not at the Chicago meeting. In looking at 32 topical areas of the discipline, his panel found that the U.S. is in the forefront or among the world leaders in all the areas. But in 12 areas, such as catalysis, bioprocess engineering, and composites, the U.S. is losing ground. Thus, although the U.S. is expected to maintain its strong position in all areas of chemical engineering, its leadership in the field is not guaranteed, and in several areas it will be strongly challenged, panelists warned. The NRC reports do not offer any recommendations—"just the facts," as Casey noted.—RON DAGANI

Ceyer

A BARELY CHIRAL MOLECULE, EXPOSED

(R)-[D,D 2 ,D 3 ]neopentane. Ultimately, Christian G. Bochet, a synthetic organic chemist at Fribourg, stepped up to the challenge. "The quick and naive retro synthetic analysis that I first drew on the back of an envelope looked easy," BoSPECTROSCOPY: Configuration study chet recalls. "At the fifth version, a week later, we knew pushes Raman technique to its limits that it would take considerably more time." In fact, crafting the synthesis ate up an entire year. The ninestep process that came out of this effort began with 2-methyl-2-butenoic acid and a chiral oxazolidinone IBRATIONAL SPECTROSCOPY has revealed derivative. It yielded a few milligrams of a single enanthe relative spatial arrangement of atoms within tiomer of the deuterated neopentane. a molecule that features "structural chirality of the utmost delicacy," according to Laurence D. Barron, Hug's postdoc, Jacques Haesler, then measured the a chemist at the University of Glasgow, compound's Raman optical activity in in Scotland. "Were he alive today, Lord order to check its absolute configuraCDH Kelvin"—who introduced the concept tion. Hug and Haesler used an ingenious 'CHQ of chirality early in the 20th century— optical technique to remove noise from HD2C CD "would be impressed with the work." the resulting signal. Comparison of the The molecule in question is a neodata with the calculated spectrum con(ft)-[D,D 2 ,D 3 ]Neopentane pentane in which some of the methylfirmed the synthesized neopentane's group hydrogens are replaced by deuconfiguration (Nature 2007,446,526). teriums. Until recently, it didn't even exist. Barron, who in the early 1970s was the first to observe Raman optical activity, notes in a Nature comA couple of years ago, spectroscopist Werner Hug of mentary that "it would be very difficult, if not imposthe University of Fribourg, in Switzerland, calculated sible, to determine the absolute configuration using the vibrational optical activity spectrum for the comany other existing physical technique." pound. "But it's very unsatisfactory to just have promising computed numbers without being able to confirm Hug, who has been instrumental in developing this them by an experiment," he says. Raman method, adds that the results "demonstrate the So he began searching for a chemist willing to make great power" of the approach.—SOPHIE ROVNER

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"The quick and naïve retrosynthetic analysis that I first drew on the back of an envelope looked easy. At the fifth version, a week later, we knew that it would take considerably more time" -CHRISTIAN B0CHET