Tetrabutylammonium is a
quaternary ammonium cation
In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure , where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion () and the primary, secondary, ...
with the formula , also denoted (where Bu =
butyl group). It is used in the research laboratory to prepare
lipophilic
Lipophilicity (from Greek language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are c ...
salts of inorganic anions. Relative to
tetraethylammonium
Tetraethylammonium (TEA) is a quaternary ammonium cation with the chemical formula , consisting of four ethyl groups (, denoted Et) attached to a central nitrogen atom. It is a counterion used in the research laboratory to prepare lipophilic salt ...
derivatives, tetrabutylammonium salts are more lipophilic but
crystallize less readily.
Derivatives
Some tetrabutylammonium salts of simple anions include:
*
tetrabutylammonium fluoride, a
desilylation reagent.
*
tetrabutylammonium bromide, a precursor to other tetrabutylammonium salts via
salt metathesis reaction
A salt metathesis reaction (also called a double displacement reaction, double replacement reaction, or double decomposition) is a type of chemical reaction in which two ionic compounds in aqueous solution exchange their component ions to form two ...
s.
*
tetrabutylammonium iodide, a low cost catalyst.
*
tetrabutylammonium triiodide, a common carrier of the
triiodide
In chemistry, triiodide usually refers to the triiodide ion, . This anion, one of the polyhalogen ions, is composed of three iodine atoms. It is formed by combining aqueous solutions of iodide salts and iodine. Some salts of the anion have been ...
anion used in chemical synthesis.
*
tetrabutylammonium hydroxide, a precursor to other tetrabutylammonium salts via acid-base reactions.
*
tetrabutylammonium hexafluorophosphate, an electrolyte for nonaqueous electrochemistry.
Some tetrabutylammonium salts of more complex examples include:
*
polyoxometalate
In chemistry, a polyoxometalate (abbreviated POM) is a polyatomic ion, usually an anion, that consists of three or more transition metal oxyanions linked together by shared oxygen atoms to form closed 3-dimensional frameworks. The metal atoms are ...
s.
*NS.
*
metal carbonyl anions.
*Synthetic
iron-sulfur clusters such as
*
Octachlorodirhenate ().
[{{cite book, first1=T. J. , last1=Barder, first2=R. A., last2=Walton, title=Inorganic Syntheses, chapter=Tetrabutylammonium Octachlorodirhenate(III), year=1990, volume=28, pages=332–334, doi=10.1002/9780470132593.ch83, isbn=9780470132593]
See also
*
N-Butyllithium
References
Reagents for organic chemistry
Quaternary ammonium compounds
Cations