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. 2014 Jun 20;79(12):5412-9.
doi: 10.1021/jo402814c. Epub 2014 May 29.

Tautomeric properties and gas-phase structure of acetylacetone

Natalya V Belova  1 , Heinz Oberhammer, Nguen Hoang Trang, Georgiy V Girichev
Affiliations

Tautomeric properties and gas-phase structure of acetylacetone

Natalya V Belova et al. J Org Chem. .

Abstract

The tautomeric and structural properties of acetylacetone, CH3C(O)CH2C(O)CH3, have been studied by gas-phase electron diffraction (GED) and quantum chemical calculations (B3LYP and MP2 approximation with different basis sets up to aug-cc-pVTZ). The analysis of GED intensities resulted in the presence of 100(3)% of the enol tautomer at 300(5) K and 64(5)% of the enol at 671(7) K. The enol tautomer possesses Cs symmetry with a planar ring and strongly asymmetric hydrogen bond. The diketo form possesses C2 symmetry. The experimental geometric parameters of both tautomeric forms are reproduced very closely by B3LYP/aug-cc-pVTZ and MP2/cc-pVTZ methods.

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