Nitrosylsulfuric acid
Encyclopedia
Nitrosylsulfuric acid is the chemical compound
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

 with the formula NOHSO4.

This salt is a source of the NO+ ion, It can also be viewed as the mixed acid anhydride of sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...

 and nitrous acid
Nitrous acid
Nitrous acid is a weak and monobasic acid known only in solution and in the form of nitrite salts.Nitrous acid is used to make diazides from amines; this occurs by nucleophilic attack of the amine onto the nitrite, reprotonation by the surrounding solvent, and double-elimination of water...

:
HNO2 + H2SO4 → NOHSO4 +H2O


NOHSO4 is useful in organic chemistry
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

 to prepare diazonium salts from amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...

s. A typical procedure entails dissolving sodium nitrite
Sodium nitrite
Sodium nitrite is the inorganic compound with the chemical formula NaNO2. It is a white to slight yellowish crystalline powder that is very soluble in water and is hygroscopic...

 in concentrated sulfuric acid in an ice bath.

Related NO-delivery reagents include nitrosonium tetrafluoroborate
Nitrosonium tetrafluoroborate
Nitrosonium tetrafluoroborate, also called nitrosyl tetrafluoroborate, is a chemical compound with the chemical formula NOBF4. This colourless solid finds use in organic synthesis as a nitrosating agent....

, [NO]BF4, and nitrosyl chloride
Nitrosyl chloride
Nitrosyl chloride is the chemical compound NOCl. It is a yellow gas that is most commonly encountered as a decomposition product of aqua regia, a mixture of hydrochloric acid and nitric acid...

.
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