Journal of Physical Chemistry A: Molecules, Spectroscopy, Kinetics, Environment and General Theory 2012-04-05

Tautomeric and conformational properties of benzoylacetone, CH3-C(O)-CH2-C(O)-C6H5: gas-phase electron diffraction and quantum chemical study.

Natalya V Belova, Georgiy V Girichev, Heinz Oberhammer, Trang Nguen Hoang, Sergey A Shlykov

Index: J. Phys. Chem. A 116(13) , 3428-35, (2012)

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Abstract

Tautomeric and structural properties of benzoylacetone, CH(3)-C(O)-CH(2)-C(O)-C(6)H(5), 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). Analysis of GED intensities resulted in the presence of 100% enol tautomer at 331(5) K. The existence of two possible enol conformers in about equal amounts is confirmed by both GED and quantum chemical results. In both conformers the enol ring possesses C(s) symmetry with a strongly asymmetric hydrogen bond. The experimental geometric parameters are reproduced very closely by the B3LYP/cc-pVTZ method.