Tautomeric Properties and Gas-Phase Structure of Acetylacetone

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• 作者：Natalya V. Belova ; Heinz Oberhammer ; Nguen Hoang Trang ; Georgiy V. Girichev
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：June 20, 2014
• 年：2014
• 卷：79
• 期：12
• 页码：5412-5419
• 全文大小：323K
• 年卷期：v.79,no.12(June 20, 2014)
• ISSN：1520-6904

文摘

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 C_s 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.