Tetramethylammonium fluoride

Tetramethylammonium fluoride is the quaternary ammonium salt with the formula ₄NF. This colorless solid is a source of “naked fluoride", that is fluoride ions not connected to a metal atom in a complex. Most other soluble salts of fluoride are in fact bifluorides, HF₂^–. Tetramethylammonium fluoride is produced by combining tetramethylammonium hydroxide and hydrogen fluoride in isopropanol. Due to the high basicity of the fluoride anion, the salt reacts slowly with acetonitrile, inducing its dimerization to CH₃C=CHCN, which co-crystallizes.

Related salts

Tetramethylphosphonium fluoride ₄PF forms stable solutions in acetonitrile. It is prepared by reaction of the ylide with potassium bifluoride:
A more elaborate phosphazenium salt ₃P]₂N⁺F⁻) is also known.
Tetrabutylammonium fluoride has been prepared by the reaction of hexafluorobenzene and tetrabutylammonium cyanide. This salt was once suspected of being unstable owing to Hofmann degradation.

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