Tautomeric Properties and Gas-Phase Structure of Acetylacetone

被引：34

作者：

Belova, Natalya V. ^{[1
]}

Oberhammer, Heinz ^{[2
]}

Trang, Nguen Hoang ^{[1
]}

Girichev, Georgiy V. ^{[1
]}

机构：

[1] Ivanovo State Univ Chem & Technol, Res Inst Thermodynam & Kinet Chem Proc, Ivanovo 153460, Russia

[2] Univ Tubingen, Inst Phys & Theoret Chem, D-72076 Tubingen, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 12期

基金：

俄罗斯基础研究基金会;

关键词：

KETO-ENOL-TAUTOMERISM; CONFORMATIONAL PROPERTIES; ELECTRON-DIFFRACTION; METHYL ACETOACETATE; CRYSTAL DISORDER; BETA-DIKETONES; FT-IR; ENTHALPY; SPECTROSCOPY; FORMS;

D O I：

10.1021/jo402814c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 C-2 symmetry. The experimental geometric parameters of both tautomeric forms are reproduced very closely by B3LYP/aug-cc-pVTZ and MP2/cc-pVTZ methods.

引用

页码：5412 / 5419

页数：8

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