A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP

	A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP
	Bian, Guangling 1,2; Fan, Hongjun 3; Yang, Shiwei 1,2; Yue, Huifeng 1,2; Huang, Huayin 1,2; Zong, Hua 1,2; Song, Ling 1,2
刊名	journal of organic chemistry
	2013-09-20
卷号	78 期号:18 页码:9137-9142
通讯作者	ling song
产权排序	待补充
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.
学科主题	物理化学
WOS标题词	science & technology ; physical sciences
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
内容类型	期刊论文
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.