A theoretical treatment of solvent effects on the tautomeric equilibria of five-membered rings with two heteroatoms was written by Karel’son, M. M.;Katritzky, Alan R.;Szafran, Miroslaw;Zerner, Michael C.. And the article was included in Journal of the Chemical Society in 1990.COA of Formula: C3H3NO2 The following contents are mentioned in the article:
The tautomeric equilibrium constants of nine oxo and hydroxy derivatives of five-membered heterocycles containing two ring heteroatoms (nitrogen or oxygen) as calculated by the AM1 quantum chem. model agree well with literature gas-phase data. The inclusion of solvent effects through a self-consistent reaction field technique into these calculations yields results in full agreement with exptl. data obtained for these systems in aqueous solution It is not possible to use the calculated energies for isolated mols. to predict the relative stabilities of these tautomers in solution Solvent effects are specific, and differentially lower the energy of one tautomer over another demonstrating in some cases a strong solvent effect on tautomeric equilibrium In general, dielec. media favor charge separation and preferentially lower the energy of species with the greater degree of charge separation In the species studied solvent reaction field effects favor ionic resonance forms of the carbonyl tautomers and hence a greater degree of aromaticity. This study involved multiple reactions and reactants, such as Isoxazol-4-ol (cas: 80348-66-9COA of Formula: C3H3NO2).
Isoxazol-4-ol (cas: 80348-66-9) belongs to isoxazole derivatives. Isoxazoles also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib (Bextra) and a neurotransmitter agonist AMPA. Isoxazole can be synthesised via a variety of methods. Examples include via a 1,3-dipolar cycloaddition of nitrile oxides with alkynes.COA of Formula: C3H3NO2
Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem