Tetra-n-butylammonium iodide

Last updated
Tetra-n-butylammonium iodide
Tetrabutylammonium iodide.svg
Names
Preferred IUPAC name
N,N,N-Tributylbutan-1-aminium iodide
Other names
TBAI
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 206-220-5
PubChem CID
  • 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 Yes check.svgY
    Key: DPKBAXPHAYBPRL-UHFFFAOYSA-M Yes check.svgY
  • 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
  • [I-].CCCC[N+](CCCC)(CCCC)CCCC
Properties
C16H36IN
Molar mass 369.3716 g/mol
AppearanceWhite powder
Melting point 147 °C (297 °F; 420 K)
Hazards
Occupational safety and health (OHS/OSH):
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.

Contents

Properties

The solid crystal of tetra-n-butylammonium iodide is in the monoclinic crystal 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]

See also

Related Research Articles

Silver bromide (AgBr) is a soft, pale-yellow, water-insoluble salt well known for its unusual sensitivity to light. This property has allowed silver halides to become the basis of modern photographic materials. AgBr is widely used in photographic films and is believed by some to have been used for making the Shroud of Turin. The salt can be found naturally as the mineral bromargyrite.

Phosphorus triiodide Chemical compound

Phosphorus triiodide (PI3) is an inorganic compound with the formula PI3. A red solid, it is a common misconception that PI3 is too unstable to be stored; it is, in fact, commercially available. It is widely used in organic chemistry for converting alcohols to alkyl iodides. It is also a powerful reducing agent. Note that phosphorus also forms a lower iodide, P2I4, but the existence of PI5 is doubtful at room temperature.

Triiodide Ion

In chemistry, triiodide usually refers to the triiodide ion, I
3
. This anion, one of the polyhalogen ions, is composed of three iodine atoms. It is formed by combining aqueous solutions of iodide salts and iodine. Some salts of the anion have been isolated, including thallium(I) triiodide (Tl+[I3]) and ammonium triiodide ([NH4]+[I3]). Triiodide is observed to be a red colour in solution.

Tetra-<i>n</i>-butylammonium fluoride Chemical compound

Tetra-n-butylammonium fluoride, commonly abbreviated to TBAF and n-Bu4NF, is a quaternary ammonium salt with the chemical formula (CH3CH2CH2CH2)4N+F. It is commercially available as the white solid trihydrate and as a solution in tetrahydrofuran. TBAF is used as a source of fluoride ion in organic solvents.

Aluminium iodide Chemical compound

Aluminium iodide is a chemical compound containing aluminium and iodine. Invariably, the name refers to a compound of the composition AlI
3
, formed by the reaction of aluminium and iodine or the action of HI on Al metal. The hexahydrate is obtained from a reaction between metallic aluminum or aluminum hydroxide with hydrogen iodide or hydroiodic acid. Like the related chloride and bromide, AlI
3
is a strong Lewis acid and will absorb water from the atmosphere. It is employed as a reagent for the scission of certain kinds of C-O and N-O bonds. It cleaves aryl ethers and deoxygenates epoxides.

The thallium halides include monohalides, where thallium has oxidation state +1, trihalides in which thallium generally has oxidation state +3, and some intermediate halides containing thallium with mixed +1 and +3 oxidation states. These materials find use in specialized optical settings, such as focusing elements in research spectrophotometers. Compared to the more common zinc selenide-based optics, materials such as thallium bromoiodide enable transmission at longer wavelengths. In the infrared, this allows for measurements as low as 350 cm−1 (28 μm), whereas zinc selenide is opaque by 21.5 μm, and ZnSe optics are generally only usable to 650 cm−1 (15 μm).

Cerium(III) bromide Chemical compound

Cerium(III) bromide is an inorganic compound with the formula CeBr3. This white hygroscopic solid is of interest as a component of scintillation counters.

Lanthanum(III) bromide (LaBr3) is an inorganic halide salt of lanthanum. When pure, it is a colorless white powder. The single crystals of LaBr3 are hexagonal crystals with melting point of 783 °C. It is highly hygroscopic and water-soluble. There are several hydrates, La3Br·x H2O, of the salt also known. It is often used as a source of lanthanum in chemical synthesis and as a scintillation material in certain applications.

Tetrabutylammonium tribromide Chemical compound

Tetrabutylammonium tribromide, abbreviated to TBATB, is a pale orange solid with the formula [N(C4H9)4]Br3. It is a salt of the lipophilic tetrabutylammonium cation and the linear tribromide anion. The salt is sometimes used as a reagent used in organic synthesis as a conveniently weighable, solid source of bromine.

Few compounds of californium have been made and studied. The only californium ion that is stable in aqueous solutions is the californium(III) cation. The other two oxidation states are IV (strong oxidizing agents) and II (strong reducing agents). The element forms a water-soluble chloride, nitrate, perchlorate, and sulfate and is precipitated as a fluoride, oxalate or hydroxide. If problems of availability of the element could be overcome, then CfBr2 and CfI2 would likely be stable.

Photoelectron photoion coincidence spectroscopy (PEPICO) is a combination of photoionization mass spectrometry and photoelectron spectroscopy. It is largely based on the photoelectric effect. Free molecules from a gas-phase sample are ionized by incident vacuum ultraviolet (VUV) radiation. In the ensuing photoionization, a cation and a photoelectron are formed for each sample molecule. The mass of the photoion is determined by time-of-flight mass spectrometry, whereas, in current setups, photoelectrons are typically detected by velocity map imaging. Electron times-of-flight are three orders of magnitude smaller than those of ions, which allows electron detection to be used as a time stamp for the ionization event, starting the clock for the ion time-of-flight analysis. In contrast with pulsed experiments, such as REMPI, in which the light pulse must act as the time stamp, this allows to use continuous light sources, e.g. a discharge lamp or a synchrotron light source. No more than several ion–electron pairs are present simultaneously in the instrument, and the electron–ion pairs belonging to a single photoionization event can be identified and detected in delayed coincidence.

Uranium(III) iodide Chemical compound

Uranium triiodide is an inorganic compound with the chemical formula UI3. It is a black solid that is soluble in water.

Tetraethylammonium chloride Chemical compound

Tetraethylammonium chloride (TEAC) is a quaternary ammonium compound with the chemical formula (C2H5)4N+Cl, sometimes written as Et4N+Cl. In appearance, it is a hygroscopic, colorless, crystalline solid. It has been used as the source of tetraethylammonium ions in pharmacological and physiological studies, but is also used in organic chemical synthesis.

Cerium nitrate Chemical compound

Cerium nitrate refers to a family of nitrates of cerium in the three or four oxidation state. Often these compounds contain water, hydroxide, or hydronium ions in addition to cerium and nitrate. Double nitrates of cerium also exist.

Tantalum(V) iodide Chemical compound

Tantalum(V) iodide is the inorganic compound with the formula Ta2I10. Its name comes from the compound's empirical formula, TaI5. It is a diamagnetic, black solid that hydrolyses readily. The compound adopts an edge-shared bioctahedral structure, which means that two TaI5 units are joined by a pair of iodide bridges. There is no bond between the Ta centres. Niobium(V) chloride, niobium(V) bromide, niobium(V) iodide, tantalum(V) chloride, and tantalum(V) bromide all share this structural motif.

The tetrabromonickelate anion contains a doubly-charged nickel atom (Ni2+) surrounded by four bromide ions in a tetrahedral arrangement. The formula is [NiBr4]2−.

Thorium(IV) nitrate Chemical compound

Thorium(IV) nitrate is a chemical compound with the formula Th(NO3)4. A white solid in its anhydrous form, it can form tetra- and pentahydrates. As a salt of thorium it is weakly radioactive.

Rhodium(III) bromide Chemical compound

Rhodium(III) bromide refers to inorganic compounds of the formula RhBr3(H2O)n where n = 0 or approximately three. Both forms are brown solids. The hydrate is soluble in water and lower alcohols. It is used to prepare rhodium bromide complexes. Rhodium bromides are similar to the chlorides, but have attracted little academic or commercial attention.

Pentaphenylphosphorus Chemical compound

Pentaphenylphosphorus is an organic phosphorane containing five phenyl groups connected to a central phosphorus atom. The phosphorus atom is considered to be in the +5 oxidation state. The chemical formula could be written as P(C6H5)5 or Ph5P, where Ph represents the phenyl group. It was discovered and reported in 1949 by Georg Wittig.

Tetra-n-butylammonium triiodide (TBAI3) is a quaternary ammonium salt with a triiodide counterion. It is a common carrier of the triiodide used in chemical synthesis of organic conductors and superconductors. In crystals, the triiodide moieties are linear and shows high crystallinity. The crystals have a black appearance with a needle or plate-like habit.

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. 1 2 3 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.