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Synthesis

Trifluoroselenoacetic Acid Makes Its Debut

Chemists report the first synthesis of CF3C(O)SeH, a previously unknown strong acid with synthetic potential

by Stephen K. Ritter
October 25, 2010 | A version of this story appeared in Volume 88, Issue 43

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Credit: Inorg. Chem.
Molecular models depict trifluoroselenoacetic acid's syn-anti and anti-syn conformers.
Credit: Inorg. Chem.
Molecular models depict trifluoroselenoacetic acid's syn-anti and anti-syn conformers.

An international team of chemists is reporting the first synthesis of trifluoroselenoacetic acid, CF3C(O)SeH, a previously unknown strong acid with potential uses in organic synthesis (Inorg. Chem., DOI: 10.1021/ic101254k). The parent compound trifluoroacetic acid, CF3C(O)OH, was first prepared in 1922. It’s a strong acid that has proven useful as a solvent and reagent in organic chemistry. In 1960, chemists reported the synthesis of the sulfur analog, trifluorothioacetic acid, CF3C(O)SH, which is a slightly stronger acid and also a useful reagent. Now, Rosana M. Romano of the National University of La Plata, in Argentina, and colleagues have prepared the selenium version, which is estimated to be an even slightly stronger acid. Building on their earlier work to prepare the nonfluorinated selenoacetic acid, CH3C(O)SeH, the researchers made CF3C(O)SeH by treating CF3C(O)OH with an excess amount of Woollins’ reagent, (C6H5)2P2Se4. They isolated the new compound, which is a colorless liquid estimated to boil at 46 °C, with vacuum-line techniques and characterized it with a battery of spectroscopic tests and theoretical calculations. The compound’s reactivity, including photolysis to generate CF3 radicals, suggests it could be another useful reagent.

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Credit: Inorg. Chem.
A model of CF3C(O)SeH with its computed electron density.
Credit: Inorg. Chem.
A model of CF3C(O)SeH with its computed electron density.

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