Preparation and structural analysis of (±)-threo-ritalinic acid.

IF 0.8 4区化学

Acta crystallographica. Section C, Crystal structure communications Pub Date : 2013-11-01 Epub Date: 2013-10-19 DOI:10.1107/S010827011302595X

Sara Wyss, Irmgard A Werner, W Bernd Schweizer, Simon M Ametamey, Selena Milicevic Sephton

引用次数: 2

Abstract

Hydrolysis of the methyl ester (±)-threo-methyl phenidate afforded the free acid in 40% yield, viz. (±)-threo-ritalinic acid, C13H17NO2. Hydrolysis and subsequent crystallization were accomplished at pH values between 5 and 7 to yield colourless prisms which were analysed by X-ray crystallography. Crystals of (±)-threo-ritalinic acid belong to the P21/n space group and form intermolecular hydrogen bonds. An antiperiplanar disposition of the H atoms of the (HOOC-)CH-CHpy group (py is pyridine) was found in both the solid (diffraction analysis) and solution state (NMR analysis). It was also determined that (±)-threo-ritalinic acid conforms to the minimization of negative gauche(+)-gauche(-) interactions.

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(±)-三苯胺酸的制备及结构分析。

(±)-三苯甲酸甲酯水解得到的游离酸收率为40%，即(±)-三苯甲酸，C13H17NO2。水解和随后的结晶在pH值5和7之间完成，得到无色棱镜，通过x射线晶体学分析。(±)-三利他酸晶体属于P21/n空间基团，并形成分子间氢键。(HOOC-)CH-CHpy基团(py为吡啶)的H原子在固体(衍射分析)和溶液(核磁共振分析)中都有反周面分布。还确定了(±)-三利他酸符合负的间扭式(+)-间扭式(-)相互作用的最小化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Acta crystallographica. Section C, Crystal structure communications 化学-晶体学

自引率

12.50%

发文量

审稿时长

1 months

期刊介绍： Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.