Tetrabutylammonium
Tetrabutylammonium is a quaternary ammonium cation with the formula [N(C4H9)4]+. 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.
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| Preferred IUPAC name
N,N,N-Tributylbutan-1-aminium | |
| Other names
Tetrabutylammonium Tetrabutylazanium | |
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3D model (JSmol) |
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| Properties | |
| C16H36N− | |
| Molar mass | 242.472 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).
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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 [Fe4S4(SPh)4]2−[5]
- Octachlorodirhenate ([Re2Cl8]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.
- Klemperer, W. G. (1990). "Tetrabutylammonium Isopolyoxometalates". Inorganic Syntheses. Inorganic Syntheses. Vol. 27. p. 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. Vol. 18. p. 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. Vol. 26. p. 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. Vol. 21. p. 33–37. doi:10.1002/9780470132524.ch9. ISBN 9780470132524..
- Barder, T. J.; Walton, R. A. (1990). "Tetrabutylammonium Octachlorodirhenate(III)". Inorganic Syntheses. Inorganic Syntheses. Vol. 28. p. 332–334. doi:10.1002/9780470132593.ch83. ISBN 9780470132593.
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