:Tetrabutylammonium
{{Short description|Polyatomic ion (N(C₄H₉)₄, charge +1)}}
{{chembox
|Watchedfields = changed
|Name = Tetrabutylammonium
|ImageFile = Tetrabutylammonium.svg
|PIN = N,N,N-Tributylbutan-1-aminium
|OtherNames = Tetrabutylammonium
Tetrabutylazanium
|Section1={{Chembox Identifiers
|CASNo = 10549-76-5
|CASNo_Ref = {{cascite|correct|CAS}}
|ChEBI = 45825
|ChEMBL = 1236196
|ChemSpiderID = 15220
|DrugBank = DB01851
|DTXSID = DTXSID3045011
|PubChem = 16028
|UNII = CBU2X6BBJR
|StdInChI = 1S/C16H36N/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4/h5-16H2,1-4H3/q+1
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = DZLFLBLQUQXARW-UHFFFAOYSA-N
|SMILES = CCCC[N+](CCCC)(CCCC)CCCC
}}
|Section2={{Chembox Properties
|C=16 | H=36 | N=1
|Formula_Charge = +
}}
|Section8={{Chembox Related
| OtherCompounds = tetrabutylammonium fluoride
tetrabutylammonium bromide
tetrabutylammonium hydroxide
tetrabutylammonium hydroxide
tetrabutylammonium hexafluorophosphate
}}
}}
Tetrabutylammonium is a quaternary ammonium cation with the formula {{chem2|[N(C4H9)4]+}}, also denoted {{chem2|[NBu4]+}} (where Bu = butyl group). It is used in the research laboratory to prepare lipophilic salts of inorganic anions. Relative to tetraethylammonium 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 reactions.
- tetrabutylammonium iodide, a low cost catalyst.{{Cite journal |last1=Shi |first1=Erbo |last2=Shao |first2=Ying |last3=Chen |first3=Shulin |last4=Hu |first4=Huayou |last5=Liu |first5=Zhaojun |last6=Zhang |first6=Jie |last7=Wan |first7=Xiaobing |date=2012-07-06 |title=Tetrabutylammonium Iodide Catalyzed Synthesis of Allylic Ester with tert-Butyl Hydroperoxide as an Oxidant |url=https://doi.org/10.1021/ol3013606 |journal=Organic Letters |volume=14 |issue=13 |pages=3384–3387 |doi=10.1021/ol3013606 |pmid=22731787 |issn=1523-7060|url-access=subscription }}
- tetrabutylammonium triiodide, a common carrier of the triiodide 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:
- polyoxometalates.{{cite book|author1-link=Walter G. Klemperer|first1=W. G.|last1=Klemperer|title=Inorganic Syntheses|chapter=Tetrabutylammonium Isopolyoxometalates|year=1990|volume=27|pages=74–85 |doi=10.1002/9780470132586.ch15|isbn=9780470132586}}
- NS{{su|b=4|p=−}}.{{cite book|first1=J.|last1=Bojes|first2=T. |last2=Chivers|first3=I.|last3=Drummond |title=Inorganic Syntheses|chapter=Heptathiazocine(Heptasulfurimide) and Tetrabutylammonium Tetrathionitrate|year=1978|volume=18 |pages=203–206|doi=10.1002/9780470132494.ch36|isbn=9780470132494}}
- metal carbonyl anions.{{cite book|first1=A. |last1=Ceriotti|first2=G. |last2=Longoni|first3=M.|last3= Marchionna|chapter=Bis(Tetrabutylammonium) Hexa-μ-Carbonyl-Hexacarbonylhexaplatinate(2 -), [N(C 4 H 9 ) 4 ] 2 [Pt 6 (Co) 6 (μ-Co) 6 ] |title=Inorganic Syntheses|year=1989|volume=26|pages=316–319 |doi=10.1002/9780470132579.ch57|isbn=978-0-471-50485-6 }}
- Synthetic iron-sulfur clusters such as {{chem2|[Fe4S4(SPh)4](2-)}}{{cite book|series=Inorganic Syntheses|first1=George |last1=Christou|first2=C. David|last2=Garner|first3=A.|last3=Balasubramaniam|first4=Brian|last4=Ridge|first5=H. N.|last5=Rydon|title=Tetranuclear Iron-Sulfur and Iron-Selenium Clusters|chapter=9. Tetranuclear Iron-Sulfur and Iron-Selenium Clusters |year=1982|volume=21|pages=33–37|doi=10.1002/9780470132524.ch9|isbn=9780470132524 }}.
- Octachlorodirhenate ({{chem2|[Re2Cl8](2-)}}).{{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}}