Ab initio study of the structure and tautomerism of internally hydrogen-bonded aromatic carbonyls: Salicylaldehyde and o-hydroxyacetophenone

摘要: We carried out an ab initio study on salicylaldehyde ando-hydroxyacetophenone with full optimization at the 3–21G level. The most stable conformation of two compounds was that including intramolecular hydrogen bond, energy and structural effects which were estimated. also studied stability respective tautomers arising from a proton transfer. Such are quinoid in nature, implies loss aromatic character benzene ring hence leads to major destabilization. Thus, tautomerization potential curve featured inverse barrier only 2.1 kJ/mol; this not even present ino-hydroxyacetophenone owing effect methyl group, thus overcome low tautomer. In some single-point calculations 6–31G** level out. both these give rise increase barriers.