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Vol. 34 No. 6
November-December 2012

Stamps International |

See also www.iupac.org/publications/ci/indexes/stamps.html


Grignard's Gift to Chemistry

More than a century after their inception, Grignard reagents are still among the most common and versatile reagents used in organic synthesis, and are a staple of every modern organic chemistry textbook. It was in 1900 that Victor Grignard (1871–1935), a young French chemist conducting his Ph.D. thesis research under the supervision of Philippe Barbier at the University of Lyon, discovered that alkyl- or arylmagnesium halides could be readily used to prepare a variety of alcohols starting from simple aldehydes or ketones. This was a revolutionary yet straightforward method for the formation of carbon–carbon bonds and, within a decade, more than 700 papers on the application of the novel reagents were published worldwide. Almost exactly 100 years ago, Grignard shared the 1912 Nobel Prize in Chemistry with a fellow Frenchman, Paul Sabatier (1854–1941), who pioneered the application of finely divided metals as catalysts for the hydrogenation of organic compounds.

Although Grignard reagents are conventionally represented by the formula RMgX (R = alkyl or aryl, X = halide), they exist in solution as a complex mixture of species whose ratio depends on concentration, temperature, the steric and electronic properties of R and X, and the Lewis basicity of the solvent (i.e., the degree of solvation). The so-called Schlenk equilibrium was extensively studied by the German chemist Wilhelm Schlenk (1879–1943), who also conducted groundbreaking studies with organolithium reagents and developed an array of elegant techniques and specialized glassware to handle air-sensitive compounds.

The French stamp illustrated in this note was issued in 1971 on the occasion of Grignard's birth centennial. It features a portrait of the famous chemist (not to mention his conspicuous mustache), some laboratory equipment, and the reverse side of his Nobel medal. Grignard has been deservedly honored over time in multiple ways but perhaps the most unusual tribute is also one of the most recent: In 2009, the International Astronomical Union (one of IUPAC's sister organizations) approved the name Grignard for a 12.2-kilometer impact crater located near the northern pole on the Moon!

For a recent biograhical sketch of Grignard and Sabatier, see: Kagan, H.B. Angew. Chem. Int. Ed. 2012, 51, 7376-7382.

Written by Daniel Rabinovich <drabinov@uncc.edu>.


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