Chemistry:Tetrabutylammonium
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Short description: Polyatomic ion (N(C₄H₉)₄, charge +1)
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| Preferred IUPAC name
N,N,N-Tributylbutan-1-aminium | |
| Other names
Tetrabutylammonium
Tetrabutylazanium | |
| Identifiers | |
3D model (JSmol)
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CompTox Dashboard (EPA)
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| Properties | |
| C16H36N+ | |
| Molar mass | 242.470 g·mol−1 |
| Related compounds | |
Related compounds
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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). | |
| Infobox references | |
Tetrabutylammonium is a quaternary ammonium cation with the formula [N(C
4H
9)
4]+
, also denoted [NBu
4]+
(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.[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 [Fe
4S
4(SPh)
4]2−[5] - Octachlorodirhenate ([Re
2Cl
8]2−).[6]
See also
References
- ↑ 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. https://doi.org/10.1021/ol3013606.
- ↑ Klemperer, W. G. (1990). "Tetrabutylammonium Isopolyoxometalates". Inorganic Syntheses. Inorganic Syntheses. 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. Inorganic Syntheses. 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(C4H9)4]2[Pt6(CO)6(μ-CO)6]. Inorganic Syntheses. 26. pp. 316–319. doi:10.1002/9780470132579.ch57.
- ↑ 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. 21. pp. 33–37. doi:10.1002/9780470132524.ch9. ISBN 9780470132524..
- ↑ Barder, T. J.; Walton, R. A. (1990). "Tetrabutylammonium Octachlorodirhenate(III)". Inorganic Syntheses. Inorganic Syntheses. 28. pp. 332–334. doi:10.1002/9780470132593.ch83. ISBN 9780470132593.
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