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3-(3-羟基-3-苯基-2-丙烯酰基)苯甲酸甲酯的合成与晶体结构

Synthesis and crystal structure of methyl 3-(3-hy-droxy-3-phenyl-prop-2-eno-yl)benzoate.

作者信息

Zharinova Irina S, Bilyalova Alfiya A, Bezzubov Stanislav I

机构信息

Department of Chemistry, Lomonosov Moscow State University, Lenin's Hills 1/3, Moscow 119991, Russian Federation.

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskiy pr. 31, Moscow 119991, Russian Federation.

出版信息

Acta Crystallogr E Crystallogr Commun. 2018 May 18;74(Pt 6):816-819. doi: 10.1107/S2056989018007259. eCollection 2018 Jun 1.

Abstract

The title compound, CHO, was synthesized under mild conditions and characterized by various analytical techniques. Combined NMR and X-ray diffraction data show that the substance exists exclusively in the enol tautomeric form. An intra-molecular ⋯O=C-C=C-OH⋯ hydrogen bond is present in the mol-ecular structure. The analysis of the difference density map disclosed two adjacent positions of a disordered hydrogen atom taking part in this hydrogen bond, indicating the presence of two enol tautomers in the crystal. The enol mol-ecules are assembled through numerous C-H⋯π and π-π as well as weak C(ar-yl)-H⋯O inter-actions, thus forming a dense crystal packing. The obtained substance was also studied by UV-Vis spectroscopy and cyclic voltammetry.

摘要

标题化合物CHO在温和条件下合成,并通过各种分析技术进行了表征。结合核磁共振和X射线衍射数据表明,该物质仅以烯醇互变异构体形式存在。分子结构中存在分子内⋯O=C-C=C-OH⋯氢键。对差分密度图的分析揭示了参与该氢键的无序氢原子的两个相邻位置,表明晶体中存在两种烯醇互变异构体。烯醇分子通过大量的C-H⋯π和π-π以及弱的C(芳基)-H⋯O相互作用组装在一起,从而形成紧密的晶体堆积。还通过紫外-可见光谱和循环伏安法对所得物质进行了研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/df1d/6002825/b2031bebb62f/e-74-00816-fig1.jpg

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