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学科主题: 物理化学
题名: A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP
作者: Bian, Guangling1, 2;  Fan, Hongjun3;  Yang, Shiwei1, 2;  Yue, Huifeng1, 2;  Huang, Huayin1, 2;  Zong, Hua1, 2;  Song, Ling1, 2
通讯作者: Ling Song
刊名: JOURNAL OF ORGANIC CHEMISTRY
发表日期: 2013-09-20
DOI: 10.1021/jo4013546
卷: 78, 期:18, 页:9137-9142
收录类别: SCI
合作性质: 
文章类型: Article
部门归属: 11
项目归属: 1102
产权排名: 待补充
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Organic
资助者: 2,2
研究领域[WOS]: Chemistry
英文摘要: A simple chiral bisthiourea has been used as a highly effective and practical chemical solvating agent (CSA) for diverse alpha-carboxylic acids in the presence of DMAP. Excellent enantiodiscrimination based on well-resolved alpha-H NMR signals of the enantiomers of carboxylic acids can be obtained without interference from the chiral bisthiourea and DMAP. To check the practicality of the chiral bisthiourea/DMAP for enantiomeric determination, the ee values of mandelic acid (MA) samples over a wide ee range were determined by integration of the alpha-H signal of MA in H-1 NMR. A discrimination mechanism is proposed, that the formation of two diasteromeric ternary complexes between the chiral bisthiourea and two in situ formed enantiomeric carboxylate-DMAPH(+) ion pairs discriminates the enantiomers of carboxylic acids. Computational modeling studies show that the chemical shift value of alpha-H of (S)-MA is greater than that of (R)-MA in ternary complexes, which is consistent with experimental observation. 1D and 2D NOESY spectra demonstrate the intermolecular noncovalent interactions between the protons on the aromatic rings of chiral bisthiourea and alpha-H of the enantiomers of racemic alpha-methoxy phenylacetic acids in the complexes.
关键词[WOS]: SHIFT-REAGENT ;  NMR ENANTIODISCRIMINATION ;  STRUCTURALLY SIMPLE ;  ALPHA-HYDROXY ;  RECEPTOR ;  RECOGNITION ;  DISCRIMINATION ;  DERIVATIVES ;  MACROCYCLES ;  ENANTIOMERS
语种: 英语
原文出处: 查看原文
WOS记录号: WOS:000330159500021
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/119415
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Fujian, Peoples R China
2.Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China
3.Chinese Acad Sci, Dalian Inst Chem Phys, State Lab Mol React Dynam, Dalian 116023, Peoples R China

Recommended Citation:
Bian, Guangling,Fan, Hongjun,Yang, Shiwei,et al. A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP[J]. JOURNAL OF ORGANIC CHEMISTRY,2013,78(18):9137-9142.
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