Tetra-n-butylammonium iodide

Tetra-n-butylammonium iodide
Names
	IUPAC name Tetra-n-butylammonium iodide
	Other names TBAI
Identifiers
CAS Number	311-28-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	60875 ;
EC Number	206-220-5;
PubChem CID	329769349;
	InChI InChI=1S/C16H36N.HI/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1 Key: DPKBAXPHAYBPRL-UHFFFAOYSA-M ; InChI=1S/C16H36N.HI/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1;
	SMILES [I-].CCCC[N+](CCCC)(CCCC)CCCC;
Properties
Chemical formula	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

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.

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 Δ_fH⁰ 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

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.
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.
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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[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.

[nag-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.