About this deal
Orthoperiodic acid forms monoclinic crystals ( space group P2 1/ n) consisting of a slightly deformed IO 6 octahedron interlinked via bridging hydrogens. Most notably periodic acid will cleave vicinal diols into two aldehyde or ketone fragments ( Malaprade reaction). Periodate is part of a series of oxyacids in which iodine can assume oxidation states of −1, +1, +3, +5, or +7. Because the process requires vicinal diols, periodate oxidation is often used to selectively label the 3′-termini of RNA ( ribose has vicinal diols) instead of DNA as deoxyribose does not have vicinal diols.
This is commercially available, but can also be produced by the oxidation of iodates with chlorine and sodium hydroxide. H 5 IO 6 + H + + 2 e − ⟶ IO 3 − + 3 H 2 O {\displaystyle {\ce {H5IO6 + H+ + 2e- -> IO3- + 3 H2O}}} E° = 1. F. Holleman; continued by Egon Wiberg; translated by Mary Eagleson, William Brewer; revised by Bernhard J.The structure of metaperiodic acid also includes IO 6 octahedra, however these are connected via cis-edge-sharing with bridging oxygens to form one-dimensional infinite chains. H 3 IO 6 2 − ↽ − − ⇀ H 2 IO 6 3 − + H + {\displaystyle {\ce {H3IO6 Metaperiodic acid can also be prepared from various orthoperiodates by treatment with dilute nitric acid.
This can be useful in determining the structure of carbohydrates as periodic acid can be used to open saccharide rings. It can combine with a number of counter ions to form periodates, which may also be regarded as the salts of periodic acid. It can exist in two forms: orthoperiodic acid, with the chemical formula H 5IO 6, and metaperiodic acid, which has the formula HIO 4. Expanding the scope of the Babler–Dauben oxidation: 1,3-oxidative transposition of secondary allylic alcohols". It is one of a number of oxyanions of iodine and is the highest in the series, with iodine existing in oxidation state +7.This process is often used in labeling saccharides with fluorescent molecules or other tags such as biotin.