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« Too much end-of-semester grading and too much NMR... | Main | P-Toluenesulfonic Acid (Greasy sulfuric acid) »

Tetrabutylammonium Fluoride (Fluoride Soaps)

Category: Synthesis
Posted on: December 18, 2006 8:18 PM, by Molecule of the Day

The fluoride ion is important to synthetic chemistry, often because it can be used to cleave silyl ethers (the silicon analogue of a carbon ether). Fluoride is notorious for holding onto water (like any tiny ion - lithium is about as bad), so even an "anhydrous" solution of TBAF in (say) THF will often contain ca 5% water. The less water you have, the more "naked" fluoride anion you have, which is much, much more reactive than aquated fluoride.

InChI=1/C16H36N.FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1

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Comments

very interesting...great blog, too bad i only discovered it recently.

Posted by: lo | December 22, 2006 1:23 PM

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