Purpuric acid is a
nitrogenous
Nitrogen is the chemical element with the Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the pnictogens. It is a common element in the ...
acid related to
barbituric acid
Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid ...
that yields
alloxan
Alloxan, sometimes referred to as ''alloxan hydrate'', is the name of the organic compound with the formula OC(N(H)CO)2C(OH)2. It is classified as a derivative of pyrimidine. The anhydrous derivative OC(N(H)CO)2CO is also known, as well as a dime ...
and
uramil upon
hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
. It is noteworthy for its purple-red salts, such as its
ammonium
The ammonium cation is a positively-charged polyatomic ion with the chemical formula or . It is formed by the protonation of ammonia (). Ammonium is also a general name for positively charged or protonated substituted amines and quaternary a ...
salt
murexide
Murexide (NH4C8H4N5O6, or C8H5N5O6·NH3), also called ammonium purpurate or MX, is the ammonium salt of purpuric acid. It is a purple solid that is soluble in water. The compound was once used as an indicator reagent. Aqueous solutions are yel ...
. Purpuric acid was first described in 1818 by the English chemist
William Prout
William Prout FRS (; 15 January 1785 – 9 April 1850) was an English chemist, physician, and natural theologian. He is remembered today mainly for what is called Prout's hypothesis.
Biography
Prout was born in Horton, Gloucestershire in 1 ...
(1785-1850). Though colourless itself, purpuric acid has a tendency to form red or purple-coloured salts with alkaline bases. This characteristic led the English doctor
William Hyde Wollaston
William Hyde Wollaston (; 6 August 1766 – 22 December 1828) was an English chemist and physicist who is famous for discovering the chemical elements palladium and rhodium. He also developed a way to process platinum ore into malleable ingo ...
(1766-1828) to suggest the name ''purpuric acid''.
Purpuric acid can be synthesized by
nitration
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and ...
of
uric acid
Uric acid is a heterocyclic compound of carbon, nitrogen, oxygen, and hydrogen with the formula C5H4N4O3. It forms ions and salts known as urates and acid urates, such as ammonium acid urate. Uric acid is a product of the metabolic breakdown of ...
(previously known as lithic acid). In 1818, Prout obtained lithic acid from the excrement of a
boa constrictor
The boa constrictor (scientific name also ''Boa constrictor''), also called the red-tailed boa, is a species of large, non-venomous, heavy-bodied snake that is frequently kept and bred in captivity. The boa constrictor is a member of the family B ...
(which largely consists of this substance) or else used
urinary calculi
Kidney stone disease, also known as nephrolithiasis or urolithiasis, is a crystallopathy where a solid piece of material (kidney stone) develops in the urinary tract. Kidney stones typically form in the kidney and leave the body in the urine s ...
. He dissolved the lithic acid in 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 ...
and after an
effervescence
Effervescence is the escape of gas from an aqueous solution and the foaming or fizzing that results from that release. The word effervescence is derived from the Latin verb ''fervere'' (to boil), preceded by the adverb ''ex''. It has the same lin ...
took place a purple liquid was formed. After neutralization of the solution with
ammonia
Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous was ...
, granular crystals begin to separate out.
[Andrew Ure]
"Acid (purpuric)"
''A Dictionary of Chemistry and Mineralology'', London: Thomas Tegg & Son, 1835.
Purpuric acid is insoluble in
alcohol
Alcohol most commonly refers to:
* Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom
* Alcohol (drug), an intoxicant found in alcoholic drinks
Alcohol may also refer to:
Chemicals
* Ethanol, one of sev ...
and
ether
In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...
. The
mineral acid
A mineral acid (or inorganic acid) is an acid derived from one or more inorganic compounds, as opposed to organic acids which are acidic, organic compounds. All mineral acids form hydrogen ions and the conjugate base when dissolved in water.
Cha ...
s dissolve it only when they are concentrated. It does not affect
litmus paper
Litmus is a water-soluble mixture of different dyes extracted from lichens. It is often absorbed onto filter paper to produce one of the oldest forms of pH indicator, used to test materials for acidity. It is a purple dye that is extracted fro ...
. Purpuric acid combines with the
alkali
In chemistry, an alkali (; from ar, القلوي, al-qaly, lit=ashes of the saltwort) is a basic, ionic salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as a base that dissolves in water. A solution of a ...
s,
alkaline earth
The alkaline earth metals are six chemical elements in group 2 of the periodic table. They are beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and radium (Ra).. The elements have very similar properties: they are all s ...
s, and metallic
oxide
An oxide () is a chemical compound that contains at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion of oxygen, an O2– (molecular) ion. with oxygen in the oxidation state of −2. Most of the E ...
s. It is capable of expelling
carbonic acid from the alkaline
carbonate
A carbonate is a salt of carbonic acid (H2CO3), characterized by the presence of the carbonate ion, a polyatomic ion with the formula . The word ''carbonate'' may also refer to a carbonate ester, an organic compound containing the carbonate g ...
s, by the assistance of heat, and does not combine with any other acid. Wolllaston believed that these characteristics were sufficient to distinguish it from an oxide, and to establish its character as an acid.
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References
{{reflist
Organic acids