Tetrabutylammonium is a quaternary ammonium cation with the formula [N(C4H9)4]+, also denoted [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.
| |
| Names | |
|---|---|
| Preferred IUPAC name
N,N,N-Tributylbutan-1-aminium | |
| Other names
Tetrabutylammonium
Tetrabutylazanium | |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C16H36N+ | |
| Molar mass | 242.470 g·mol−1 |
| Related compounds | |
Related compounds
|
tetrabutylammonium fluoride tetrabutylammonium bromide tetrabutylammonium hydroxide tetrabutylammonium hydroxide tetrabutylammonium hexafluorophosphate |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Derivatives
editSome 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.[1]
- 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.[2]
- NS−
4.[3] - metal carbonyl anions.[4]
- Synthetic iron-sulfur clusters such as [Fe4S4(SPh)4]2−[5]
- Octachlorodirhenate ([Re2Cl8]2−).[6]
See also
editReferences
edit- ^ Shi, Erbo; Shao, Ying; Chen, Shulin; Hu, Huayou; Liu, Zhaojun; Zhang, Jie; Wan, Xiaobing (2012-07-06). "Tetrabutylammonium Iodide Catalyzed Synthesis of Allylic Ester with tert-Butyl Hydroperoxide as an Oxidant". Organic Letters. 14 (13): 3384–3387. doi:10.1021/ol3013606. ISSN 1523-7060. PMID 22731787.
- ^ Klemperer, W. G. (1990). "Tetrabutylammonium Isopolyoxometalates". Inorganic Syntheses. Vol. 27. pp. 74–85. doi:10.1002/9780470132586.ch15. ISBN 9780470132586.
- ^ Bojes, J.; Chivers, T.; Drummond, I. (1978). "Heptathiazocine(Heptasulfurimide) and Tetrabutylammonium Tetrathionitrate". Inorganic Syntheses. Vol. 18. pp. 203–206. doi:10.1002/9780470132494.ch36. ISBN 9780470132494.
- ^ Ceriotti, A.; Longoni, G.; Marchionna, M. (1989). "Bis(Tetrabutylammonium) Hexa-μ-Carbonyl-Hexacarbonylhexaplatinate(2 -), [N(C 4 H 9 ) 4 ] 2 [Pt 6 (Co) 6 (μ-Co) 6 ]". Inorganic Syntheses. Vol. 26. pp. 316–319. doi:10.1002/9780470132579.ch57. ISBN 978-0-471-50485-6.
- ^ Christou, George; Garner, C. David; Balasubramaniam, A.; Ridge, Brian; Rydon, H. N. (1982). "9. Tetranuclear Iron-Sulfur and Iron-Selenium Clusters". Tetranuclear Iron-Sulfur and Iron-Selenium Clusters. Inorganic Syntheses. Vol. 21. pp. 33–37. doi:10.1002/9780470132524.ch9. ISBN 9780470132524..
- ^ Barder, T. J.; Walton, R. A. (1990). "Tetrabutylammonium Octachlorodirhenate(III)". Inorganic Syntheses. Vol. 28. pp. 332–334. doi:10.1002/9780470132593.ch83. ISBN 9780470132593.