Naslov
Reaction of 2-acetyl-indane-1, 3-dione with aniline - Schiff base or enamine?

Autori
Enchev, Venelin ; Ivanova, Galya ; Pavlović, Gordana ; Rogojerov, Marin ; Ahmedova, Anife ; Mitewa, Mariana

Izvornik
Journal of Molecular Structure (0022-2860) 654 (2003), 1-3; 11-20

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
2-acetyl-indane-1; 3-dione; enamine; ab initio; NMR; X-ray

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA