Hypoiodous acid

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Hypoiodous acid
IUPAC name Hypoiodous acid[note 1]
Other names Iodic(I) acid
Iodanol
Hydroxidoiodine
Identifiers
InChI InChI=1/HIO/c1-2/h2H
InChIKey GEOVEUCEIQCBKH-UHFFFAOYAY
Standard InChI InChI=1S/HIO/c1-2/h2H
Standard InChIKey GEOVEUCEIQCBKH-UHFFFAOYSA-N
CAS number [14332-21-9]
ChemSpider 109942
Properties[2]
Chemical formula HOI
Molar mass 143.91 g mol−1
Acidity (pKa) 10.70
Related compounds
Other hypohalous acids Hypofluorous acid
Hypochlorous acid
Hypobromous acid
Other compounds Iodous acid
Iodic acid
Periodic acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Hypoiodous acid, HOI, is an oxoacid of iodine. It is often considered to be only stable in aqueous solution.[2][3]

Preparation

Hypoiodous acid can be prepared in solution by the reaction of iodine with a well-stirred suspension of mercury(II) oxide.[2]

2 I2 + 2 HgO + H2O → 2 HOI + HgO·HgI2

It is also formed by the disproportionation of iodine in water, although the equilibrium concentration is only 6.4 × 10−6 mol dm−3 in a saturated iodine solution (1.3 mmol dm−3) at 25 °C.[2]

I2 + H2O HOI + H+ + I

A convenient method to prepare HOI for use in organic synthesis is the reaction of sodium hypochlorite with sodium iodide:[4]

ClO + I + H2O → HOI + Cl + OH

Hypoiodous acid is prepared in the gas phase or in matrix isolation studies by the reaction of hydroxyl radicals or atomic oxygen with iodine or iodoalkanes.[5][6][7]

Reactivity

Notes and references

Notes

  1. Hypoiodous acid is a retained name in IUPAC nomenclature.[1]

References

  1. Nomenclature of Inorganic Chemistry; IUPAC Recommendations 2005; Royal Society of Chemistry: Cambridge, 2005; p 299. ISBN 0-85404-438-8, <http://www.iupac.org/publications/books/rbook/Red_Book_2005.pdf>.
  2. 2.0 2.1 2.2 2.3 Cotton, F. Albert; Wilkinson, Geoffrey Advanced Inorganic Chemistry, 5th ed.; Wiley-Interscience: New York, 1988; pp 563–67. ISBN 0-471-84997-9.
  3. Greenwood, Norman N.; Earnshaw, A. Chemistry of the Elements; Pergamon: Oxford, 1984; pp 999–1007. ISBN 0-08-022057-6.
  4. LeBlond, Carl R.; Rossen, Kai; Gortsema, Frank P.; Zavialov, Ilia A.; Cianciosi, Steven J.; Andrews, Arthur T.; Sun, Yongkui Harvesting short-lived hypoiodous acid for efficient diastereoselective iodohydroxylation in Crixivan® synthesis. Tetrahedron Lett. 2001, 42 (49), 8603–6. DOI: 10.1016/S0040-4039(01)01863-9.
  5. Walker, N.; Tevault, D. E.; Smardzewski, R. R. Matrix reactions of ozone and oxygen atoms with hydrogen iodide. HOI formation. J. Chem. Phys. 1978, 69 (2), 564–68. DOI: 10.1063/1.436647.
  6. Barnes, I.; Becker, K. H.; Starcke, J. FTIR spectroscopic observation of gaseous HOI. Chem. Phys. Lett. 1992, 196 (6), 578–82. DOI: 10.1016/0009-2614(92)85997-O.
  7. Klaassen, Jody J.; Lindner, Jörg; Leone, Stephen R. Observation of the ν1 OH(OD) stretch of HOI and DOI by Fourier transform infrared emission spectroscopy. J. Chem. Phys. 1996, 104 (19), 7403–11. DOI: 10.1063/1.471456.

Further reading

External links

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