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Hydrogen iodide
General
Systematic name Hydrogen iodide
Other names Hydroiodic acid
Hydriodic acid
Molecular formula HI
Molar mass 127.904 g/mol
Appearance Colorless gas.
CAS number *
Properties
Density and phase 1.701 g/L, gas.
Melting point -88.6 °C (184.55 K)
Boiling point -67 °C (206.15 K)
Acidity (pKa) -10
Structure
Molecular shape Terminus
Dipole moment 0.38 D
Hazards
MSDS External MSDS
Main hazards Toxic, corrosive.
NFPA 704
Flash point Non-flammable.
R/S statement R: , , ,
S: , , ,
RTECS number MW3760000
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Other anions Hydrogen fluoride
Hydrogen chloride
Hydrogen bromide
Except where noted otherwise, data are given for
materials in their standard state (at 25°C, 100 kPa)
Chemical infobox
Hydrogen iodide (HI) is a diatomic compound that, dissolved in water, is also known as the strong acid hydroiodic acid. A concentrated solution of hydroiodic acid usually contains 48% - 57% HI by weight. HI is also used in organic and inorganic synthesis as one of the primary sources of iodine and as a reducing agent.

Properties


Hydrogen iodide is one of the strongest of all the common halide acids, despite the fact that the electronegativity of iodine is weaker than the rest of the other common halides. The high acidity is caused by the dispersal of the ionic charge over the anion. The iodide ion is much larger than the other common halides which results in the negative charge being dispersed over a large space. By contrast, a chloride ion is much smaller, meaning its negative charge is more concentrated, leading to a stronger interaction between the proton and the chloride ion. This weaker H+---I- interaction in HI facilitates dissociation of the proton from the anion .

HI → H+ + I : Ka = ~1010
HBr → H+ + Br : Ka = ~109
HCl → H+ + Cl : Ka = ~108

Preparation


The industrial preparation of HI involves the reaction of I2 with hydrazine, which also yields nitrogen gas.1
2 I2 + N2H4 → 4 HI + N2
When performed in water, the HI must be distilled.

HI can also be prepared by simply combining H2 and I2. This method is usually employed to generate high purity samples.

H2 + I2 → 2 HI

For many years, this reaction was considered to involve a simple bimolecular reaction between molecules of H2 and I2. However, when a mixture of the gases is irradiated with the wavelength of light equal to the dissociation energy of I2, about 578 nm, the rate increases significantly. This supports a mechanism whereby I2 first dissociates into 2 iodine atoms, which each attach themselves to a side of an H2 molecule and break the H -- H bond3:

H2 + I2 + 578 nm radiation → H2 + 2 I → I - - - H - - - H - - - I → 2 HI

In the laboratory, another method involves hydrolysis of PI3, the iodine equivalent of PBr3. In this method, I2 reacts with phosphorus to create phosphorus triiodide, which then reacts with water to form HI and phosphoric acid1.

3 I2 + 2 P + 6 H2O → 2 PI3 + 6 H2O → 6 HI + 2 H3PO3

Key reactions & Applications


  • HI will undergo oxidation if left open to air according to the following pathway:3
4 HI + O2 → 2H2O + 2 I2
HI + I2 → HI3
HI3 is dark brown in color, which makes aged solutions of HI often appear dark brown.
  • Like HBr and HCl, HI add to alkenes4:
HI + H2C=CH2 → H3CCH2I
HI is subject to the same Markovnikov and anti-Markovnikov guidelines as HCl and HBr.
  • HI reduces certain α-substituted ketones replacing the α substituant with a hydrogen atom.4.

References


1 Greenwood, N.N. and A. Earnshaw. The Chemistry of the Elements. 2nd ed. Oxford: Butterworth-Heineman. p 809-815. 1997.
2 Nishikata, E., T.; Ishll, and T. Ohta. “Viscosities of Aqueous Hydrochloric Acid Solutions, and Densities and Viscosities of Aqueous Hydroiodic Acid Solutions”. J. Chem. Eng. Data. 26. 254-256. 1981.
3 Holleman, A.F. Wiberg, e. Inorganic Chemistry. San Diego: Academic Press. p 371, 432-433. 2001.
4 Breton, Gary W., P. J. Kropp, and Ronald G. Harvey. “Hydrogen Iodide”. Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd. 2001. 28 Feb. 2006 http://www.mrw.interscience.wiley.com/eros/articles/rh039/sect0-fs.html .

External links


Hydrogen compounds | Iodides | Acids | Nonmetal halides

Kyselina jodovodíková | Iodwasserstoff | Waterstofjodide | Kwas jodowodorowy | Иодоводород

 

This article is licensed under the GNU Free Documentation License. It uses material from the "Hydrogen iodide".

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