Nitrolic acids are

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

s with the

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the r ...

RC(NO₂)=NOH. They are prepared by the reaction of nitroalkanes with base and nitrite sources: :RCH₂NO₂ + HNO₂ → RC(NO₂)=NOH + H₂O The conversion was first demonstrated by

Victor Meyer Viktor Meyer (8 September 18488 August 1897) was a German chemist and significant contributor to both organic and inorganic chemistry. He is best known for inventing an apparatus for determining vapour densities, the Viktor Meyer apparatus, and f ...

using

nitroethane Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor. Preparat ...

.Meyer, V.; Locher, J. "Untersuchungen über die Constitution der Nitrolsäuren (Researches on the constitution of the nitrolic acids)" Deut. Chem. Ges. Ber., 1874, volume 7, pp. 670-5. The reaction proceeds via the intermediacy of the

nitronate A nitronate (IUPAC: azinate) in organic chemistry is a functional group with the general structure . It is the anion of nitronic acid (sometimes also called an aci, or an azinic acid), a tautomer Tautomers () are structural isomers (constituti ...

anion.

Occurrence

Most nitrolic acids are laboratory curiosities. One exception is the compound HO₂C(CH₂)₄C(NO₂)=NOH, which is produced by the oxidation of

cyclohexanone Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has an odor reminiscent of acetone. Over time, samples of cyclohex ...

with

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 ni ...

. This species decomposes to

adipic acid Adipic acid or hexanedioic acid is the organic compound with the formula (CH2)4(COOH)2. From an industrial perspective, it is the most important dicarboxylic acid: about 2.5 billion kilograms of this white crystalline powder are produced annuall ...

and

nitrous oxide Nitrous oxide (dinitrogen oxide or dinitrogen monoxide), commonly known as laughing gas, nitrous, or nos, is a chemical compound, an oxide of nitrogen with the formula . At room temperature, it is a colourless non-flammable gas, and ha ...

: :HO₂C(CH₂)₄C(NO₂)=NOH → HO₂C(CH₂)₄CO₂H + N₂O This conversion is thought to be the largest anthropogenic route to N₂O, which, on a molecule-to-molecule basis, has 298 times the atmospheric heat-trapping ability of carbon dioxide. Adipic acid is a precursor to many

nylon Nylon is a generic designation for a family of synthetic polymers composed of polyamides ( repeating units linked by amide links).The polyamides may be aliphatic or semi-aromatic. Nylon is a silk-like thermoplastic, generally made from pet ...

polymers. In the end, nitrous oxide is produced in about one to one mole ratio to the adipic acid.

References

{{reflist , 30em Functional groups Organonitrogen compounds