Nitronate
A nitronate (IUPAC: azinate) in organic chemistry is an anion with the general structure Page Module:Chem2/styles.css has no content.R1R2C=N+(−O−)2, containing the Page Module:Chem2/styles.css has no content.=N+(−O−)2 functional group,[1][2] where R can be hydrogen, halogen, organyl group or other groups. It is the anion of nitronic acid Page Module:Chem2/styles.css has no content.R1R2C=N+(−O−)−OH (sometimes also called an aci-nitro compound,[3] or an azinic acid[4]), a tautomeric form of a nitro compound. Just as aldehydes and ketones can exist in equilibrium with their enol tautomer, nitro compounds exist in equilibrium with their nitronate tautomer under basic conditions. In practice they are formed by the deprotonation of the α-carbon, the pKa of which is typically around 17.
Nitronates are formed as intermediates in the Henry reaction, Hass–Bender oxidation and Nef reaction, the latter of which also demonstrates the instability of the nitronic acid form. The nitronate has two different resonance structures, one with a negative charge on the α-carbon and a double bond between the nitrogen and one of the oxygens, and another resonance structure with a double bond between the nitrogen and the α-carbon, and single bonds between the nitrogen and the oxygens.
See also
References
- ^ Page Module:Citation/CS1/styles.css has no content.Breuer, Eli; Aurich, Hans Günter; Nielsen, Arnold. Nitrones, nitronates, and nitroxides. Wiley. ISBN 9780470772195. Script error: No such module "CS1 identifiers".
- ^ Page Module:Citation/CS1/styles.css has no content.F. A. Carey, R. J. Sundberg (2004). Organische Chemie. Wiley-VCH Verlag. ISBN 3-527-29217-9.
- ^ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "aci-nitro compounds". Script error: No such module "CS1 identifiers".
- ^ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "azinic acids". Script error: No such module "CS1 identifiers".
