Metaperiodic acid
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Periodic acid ( ) is the highest
oxoacid An oxyacid, oxoacid, or ternary acid is an acid that contains oxygen. Specifically, it is a compound that contains hydrogen, oxygen, and at least one other element, with at least one hydrogen atom bonded to oxygen that can dissociate to produce ...
of
iodine Iodine is a chemical element with the symbol I and atomic number 53. The heaviest of the stable halogens, it exists as a semi-lustrous, non-metallic solid at standard conditions that melts to form a deep violet liquid at , and boils to a vi ...
, in which the iodine exists in
oxidation state In chemistry, the oxidation state, or oxidation number, is the hypothetical charge of an atom if all of its bonds to different atoms were fully ionic. It describes the degree of oxidation (loss of electrons) of an atom in a chemical compound. C ...
+7. Like all
periodate Periodate is an anion composed of iodine and oxygen. It is one of a number of oxyanions of iodine and is the highest in the series, with iodine existing in oxidation state +7. Unlike other perhalogenates, such as perchlorate, it can exist in two ...
s it can exist in two forms: orthoperiodic acid, with the
chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...
, and metaperiodic acid, which has the formula . Periodic acid was discovered by
Heinrich Gustav Magnus Heinrich Gustav Magnus (; 2 May 1802 – 4 April 1870) was a notable German experimental scientist. His training was mostly in chemistry but his later research was mostly in physics. He spent the great bulk of his career at the University of Berl ...
and C. F. Ammermüller in 1833.


Synthesis

Modern industrial scale production involves the
oxidation Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...
of a solution of
sodium iodate Sodium iodate ( Na I O3) is the sodium salt of iodic acid. Sodium iodate is an oxidizing agent. It has few uses. Preparation It can be prepared by the reacting a sodium-containing base such as sodium hydroxide with iodic acid, for example: : HI ...
under alkaline conditions, either
electrochemical Electrochemistry is the branch of physical chemistry concerned with the relationship between electrical potential difference, as a measurable and quantitative phenomenon, and identifiable chemical change, with the potential difference as an outco ...
ly on a
anode An anode is an electrode of a polarized electrical device through which conventional current enters the device. This contrasts with a cathode, an electrode of the device through which conventional current leaves the device. A common mnemonic is ...
, or by treatment with
chlorine Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate betwee ...
: : (
counter ion 160px, Polystyrene sulfonate, a cation-exchange resin, is typically supplied with as the counterion.">cation-exchange_resin.html" ;"title="Polystyrene sulfonate, a cation-exchange resin">Polystyrene sulfonate, a cation-exchange resin, is typical ...
s omitted for clarity) ''E''° = -1.6 V : Orthoperiodic acid can be dehydrated to give metaperiodic acid by heating to 100 °C under reduced pressure. : Further heating to around 150 °C gives
iodine pentoxide Iodine pentoxide is the chemical compound with the formula I2O5. This iodine oxide is the anhydride of iodic acid, and the only stable oxide of iodine. It is produced by dehydrating iodic acid at 200 °C in a stream of dry air: :2HIO3 → ...
() rather than the expected
anhydride An organic acid anhydride is an acid anhydride that is an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the pa ...
''diiodine heptoxide'' (). Metaperiodic acid can also be prepared from various orthoperiodates by treatment with dilute
nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available nitri ...
.


Properties

Orthoperiodic acid has a number of
acid dissociation constant In chemistry, an acid dissociation constant (also known as acidity constant, or acid-ionization constant; denoted ) is a quantitative measure of the strength of an acid in solution. It is the equilibrium constant for a chemical reaction :HA ...
s. The p''K''a of metaperiodic acid has not been determined. :, p''K''a = 3.29 :, p''K''a = 8.31 :, p''K''a = 11.60 There being two forms of periodic acid, it follows that two types of periodate salts are formed. For example, sodium metaperiodate, NaIO4, can be synthesised from HIO4 while sodium orthoperiodate, Na5IO6 can be synthesised from H5IO6.


Structure

Orthoperiodic acid forms
monoclinic In crystallography, the monoclinic crystal system is one of the seven crystal systems. A crystal system is described by three vectors. In the monoclinic system, the crystal is described by vectors of unequal lengths, as in the orthorhombic s ...
crystals (
space group In mathematics, physics and chemistry, a space group is the symmetry group of an object in space, usually in three dimensions. The elements of a space group (its symmetry operations) are the rigid transformations of an object that leave it unchan ...
P21/''n'') consisting of a slightly deformed octahedron interlinked via bridging hydrogens. Five I–O bond distances are in the range 1.87–1.91 Å and one I–O bond is 1.78 Å. The structure of metaperiodic acid also includes octahedra, however these are connected via ''cis''-edge-sharing with bridging oxygens to form one-dimensional infinite chains.


Reactions

Like all
periodate Periodate is an anion composed of iodine and oxygen. It is one of a number of oxyanions of iodine and is the highest in the series, with iodine existing in oxidation state +7. Unlike other perhalogenates, such as perchlorate, it can exist in two ...
s periodic acid can be used to cleave various 1,2-difunctional compounds. Most notably periodic acid will cleave vicinal
diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. The most common industrial diol is e ...
s into two
aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
or
ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...
fragments (
Malaprade reaction In organic chemistry, the Malaprade reaction or Malaprade oxidation is a glycol cleavage reaction in which a vicinal diol is oxidized by periodic acid or a periodate salt to give the corresponding carbonyl functional groups. The reaction was first ...
). This can be useful in determining the structure of
carbohydrates In organic chemistry, a carbohydrate () is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 (as in water) and thus with the empirical formula (where ''m'' may or may ...
as periodic acid can be used to open saccharide rings. This process is often used in labeling saccharides with fluorescent molecules or other tags such as
biotin Biotin (or vitamin B7) is one of the B vitamins. It is involved in a wide range of metabolic processes, both in humans and in other organisms, primarily related to the utilization of fats, carbohydrates, and amino acids. The name ''biotin'', bor ...
. Because the process requires vicinal diols, periodate oxidation is often used to selectively label the 3′-termini of
RNA Ribonucleic acid (RNA) is a polymeric molecule essential in various biological roles in coding, decoding, regulation and expression of genes. RNA and deoxyribonucleic acid ( DNA) are nucleic acids. Along with lipids, proteins, and carbohydra ...
(
ribose Ribose is a simple sugar and carbohydrate with molecular formula C5H10O5 and the linear-form composition H−(C=O)−(CHOH)4−H. The naturally-occurring form, , is a component of the ribonucleotides from which RNA is built, and so this compo ...
has vicinal diols) instead of DNA as deoxyribose does not have vicinal diols. Periodic acid is also used as an oxidising agent of moderate strength, as exemplified in the
Babler oxidation The Babler oxidation, also known as the Babler-Dauben oxidation, is an organic reaction for the Redox, oxidative transposition of tertiary Allyl group, allylic Alcohol (chemistry), alcohols to Alpha-beta Unsaturated carbonyl compounds, enones using ...
of secondary allyl alcohols which are oxidised to enones by stoichiometric amounts of orthoperiodic acid with
catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
PCC PCC may refer to: Science and technology * Pearson correlation coefficient (''r''), in statistics * Periodic counter-current chromatography, a type of affinity chromatography * Portable C Compiler, an early compiler for the C programming language ...
.


Other oxyacids

Periodate is part of a series of
oxyacid An oxyacid, oxoacid, or ternary acid is an acid that contains oxygen. Specifically, it is a compound that contains hydrogen, oxygen, and at least one other element, with at least one hydrogen atom bonded to oxygen that can dissociate to produce ...
s in which iodine can assume
oxidation state In chemistry, the oxidation state, or oxidation number, is the hypothetical charge of an atom if all of its bonds to different atoms were fully ionic. It describes the degree of oxidation (loss of electrons) of an atom in a chemical compound. C ...
s of −1, +1, +3, +5, or +7. A number of neutral
iodine oxide Iodine oxides are chemical compounds of oxygen and iodine. Iodine has only two stable oxides which are isolatable in bulk, iodine tetroxide and iodine pentoxide, but a number of other oxides are formed in trace quantities or have been hypothesized ...
s are also known.


See also

Compounds with a similar structure: *
Perchloric acid Perchloric acid is a mineral acid with the formula H Cl O4. Usually found as an aqueous solution, this colorless compound is a stronger acid than sulfuric acid, nitric acid and hydrochloric acid. It is a powerful oxidizer when hot, but aqueous sol ...
,
perbromic acid The compound perbromic acid is the inorganic compound with the formula HBrO4. It is an oxoacid of bromine. Perbromic acid is unstable and cannot be formed by displacement of chlorine from perchloric acid, as periodic acid is prepared; it can only ...
, the related perhalogenic acids *
Telluric acid Telluric acid is a chemical compound with the formula , often written as . It is a white crystalline solid made up of octahedral molecules which persist in aqueous solution. In the solid state, there are two forms, rhombohedral and monoclinic, a ...
and perxenic acid, the isoelectronic oxoacids of tellurium and xenon Compounds with similar chemistry: *
lead tetraacetate Lead(IV) acetate or lead tetraacetate is an organometallic compound with chemical formula . It is a colorless solid that is soluble in nonpolar, organic solvents, indicating that it is not a salt. It is degraded by moisture and is typically store ...
(
Criegee oxidation The Criegee oxidation is a glycol cleavage reaction in which vicinal diols are oxidized to form ketones and aldehydes using lead tetraacetate. It is analogous to the Malaprade reaction, but uses a milder oxidant. This oxidation was discovere ...
)


References

{{iodine compounds Hydrogen compounds Halogen oxoacids Iodine compounds Oxidizing acids Oxidizing agents Periodates