A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP
文献类型：期刊论文
| 作者 | Bian, Guangling1,2; Fan, Hongjun3; Yang, Shiwei1,2; Yue, Huifeng1,2; Huang, Huayin1,2; Zong, Hua1,2; Song, Ling1,2 |
| 刊名 | journal of organic chemistry
 |
| 出版日期 | 2013-09-20 |
| 卷号 | 78期号:18页码:9137-9142 |
| 产权排序 | 待补充 |
| 通讯作者 | ling song |
| 合作状况 | 英 |
| 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. |
| WOS标题词 | science & technology ; physical sciences |
| 学科主题 | 物理化学 |
| 类目[WOS] | chemistry, organic |
| 研究领域[WOS] | chemistry |
| 关键词[WOS] | shift-reagent ; nmr enantiodiscrimination ; structurally simple ; alpha-hydroxy ; receptor ; recognition ; discrimination ; derivatives ; macrocycles ; enantiomers |
| 收录类别 | SCI |
| 资助信息 | 2，2 |
| 原文出处 | 9142 |
| 语种 | 英语 |
| WOS记录号 | WOS:000330159500021 |
| 公开日期 | 2014-09-11 |
| 源URL | [http://159.226.238.44/handle/321008/119415]  |
| 专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
| 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 |
| 推荐引用方式 GB/T 7714 | 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. |
| APA | Bian, Guangling.,Fan, Hongjun.,Yang, Shiwei.,Yue, Huifeng.,Huang, Huayin.,...&Song, Ling.(2013).A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP.journal of organic chemistry,78(18),9137-9142. |
| MLA | Bian, Guangling,et al."A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP".journal of organic chemistry 78.18(2013):9137-9142. |
入库方式： OAI收割
来源：大连化学物理研究所
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