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Vol. 30 No. 1
January-February 2008

Stamps International |

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


A Hydrocarbon to Be Proud of

The stamp from Czechoslovakia illustrated in this note was issued on 4 July 1966 to celebrate the centennial of the Czech Chemical Society, which is one of the oldest chemical societies in the world and is still engaged today in all aspects of the chemical enterprise in the Czech Republic and elsewhere. Prominently featured on the stamp is a molecular diagram of adamantane, the well-known saturated hydrocarbon with a diamond-like structure and a smell reminiscent of camphor. It is a remarkably stable organic compound due to its conformational rigidity and, although it has relatively few applications, some of its derivatives (e.g., amantadine, rimantadine) are important antiviral drugs against influenza.

Why is adamantane such an iconic molecule in Czechoslovakia, anyway? It turns out that this robust cage hydrocarbon was first isolated in 1933 from a sample of Moravian crude oil analyzed by S. Landa and V. Machácek at the Czech Technical University (CTU) in Prague. Interestingly, there is another Czech connection to adamantane: It was first synthesized in 1941 by the famous Vladimir Prelog, co-recipient of the 1975 Nobel Prize in Chemistry. Although Prelog was born in Sarajevo (part of the Austro-Hungarian Empire at the time), he earned his Ph.D. from CTU in 1929 and worked in Prague until 1935. The 100th anniversary of Prelog’s birth was remembered by Bosnia and Herzegovina with a stamp issued on 25 October 2006.

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

A brief history of chemistry in the Czech Republic was published in Chemistry International (1998, Vol. 20, pp. 77–80).


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