25083-69-6Relevant academic research and scientific papers
Reaction of 2-acetyl-indane-1,3-dione with aniline - Schiff base or enamine?
Enchev, Venelin,Ivanova, Galya,Pavlovi?, Gordana,Rogojerov, Marin,Ahmedova, Anife,Mitewa, Mariana
, p. 11 - 20 (2003)
The structure of the product of the condensation reaction between 2-acetylindan-1,3-dione and aniline has been investigated in the gas phase, solution and solid state using a combination of quantum-chemical calculations, NMR and IR spectroscopies, and X-ray crystallography. Energetics of both isomers and all tautomers of the product of the reaction are predicted at HF/3-21G//HF/3-21G and HF/6-31G**//HF/3-21G levels. Geometric optimizations at HF/6-31G** level are also performed for favorable tautomers. Quantum-chemical calculations indicate that the enamine isomer, 2-[1-(N-phenylamino)-1-ethylidene]-indane-1,3-dione is favored. This is confirmed by 13C NMR spectroscopy in non-polar and polar solvents, and in the solid state by X-ray crystallography.
