Tetra-n-butylammonium iodide

Tetra-n-butylammonium iodide (TBAI) is a quaternary ammonium salt with an iodide counterion. It is used for synthesizing tetra-n-butylammonium triiodide by mixing with iodine.

Tetra-n-butylammonium iodide
Names
IUPAC name
Tetra-n-butylammonium iodide
Other names
TBAI
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 206-220-5
Properties
C16H36IN
Molar mass 369.3716 g/mol
Appearance White powder
Melting point 147 °C (297 °F; 420 K)
Hazards
Main hazards Harmful
Related compounds
Other anions
Tetrabutylammonium bromide, Tetrabutylammonium chloride, Tetrabutylammonium fluoride, Tetrabutylammonium hydroxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Properties

The solid crystal of tetra-n-butylammonium iodide is in the monoclinic cyrstal system. It has space group C2/c. The unit cell has dimensions a=14.2806 b=14.1864 c=19.5951 β=111.149. There are eight formulae in the unit cell (Z=8), which has volume 3702.4 Å3.[1]

The enthalpy of formation ΔfH0 of tetra-n-butylammonium iodide is −499 kJ/mol, which is lower than that for the bromide or chloride (−540, −564 kJ/mol).[2]

At lower temperatures with water tetra-n-butylammonium iodide forms a clathrate hydrate.[2] The tetra-n-butylammonium cation is large and hydrophobic. The absolute enthalpy of hydration (from gas phase) is −260 kJ/mol.[2]

The He(I) photoelectron spectrum of tetra-n-butylammonium iodide contains a peak at 11 eV due to the tetra-n-butylammonium cation, and at 7 and 8 eV due to iodide.[3]

References

  1. Prukała, Wiesław; Marciniec, Bogdan; Kubicki, Maciej (28 February 2007). "Tetra-n-butylammonium iodide: a space-group revision". Acta Crystallographica Section E. 63 (3): o1464–o1466. doi:10.1107/S1600536807008446.
  2. Nagano, Yatsuhisa; Mizuno, Hideki; Sakiyama, Minoru; Fujiwara, Tadayuki; Kondo, Yasuhiko (March 1991). "Hydration enthalpy of tetra-n-butylammonium ion". The Journal of Physical Chemistry. 95 (6): 2536–2540. doi:10.1021/j100159a079.
  3. Ballard, R.E.; Jones, Jimmy; Sutherland, Elizabeth (December 1984). "He(I) photoelectron spectrum of tetra-N-butylammonium iodide and bromide in solution. The effects of surface activity". Chemical Physics Letters. 112 (4): 310–312. Bibcode:1984CPL...112..310B. doi:10.1016/0009-2614(84)85747-4.
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