Tetrabutylammonium

Polyatomic ion (N(C₄H₉)₄, charge +1)

Chemical compound

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.

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

• N-Butyllithium

References

1. 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.
2. Klemperer, W. G. (1990). "Tetrabutylammonium Isopolyoxometalates". Inorganic Syntheses. Vol. 27. pp. 74–85. doi:10.1002/9780470132586.ch15. ISBN 9780470132586.
3. 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.
4. 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.
5. 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..
6. Barder, T. J.; Walton, R. A. (1990). "Tetrabutylammonium Octachlorodirhenate(III)". Inorganic Syntheses. Vol. 28. pp. 332–334. doi:10.1002/9780470132593.ch83. ISBN 9780470132593.