DICP OpenIR
Subject Area物理化学
A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP
Bian, Guangling1,2; Fan, Hongjun3; Yang, Shiwei1,2; Yue, Huifeng1,2; Huang, Huayin1,2; Zong, Hua1,2; Song, Ling1,2; Ling Song
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
2013-09-20
DOI10.1021/jo4013546
Volume78Issue:18Pages:9137-9142
Indexed BySCI
Cooperation Status
SubtypeArticle
Department11
Funding Project1102
Contribution Rank待补充
WOS HeadingsScience & Technology ; Physical Sciences
Funding Organization2,2 ; 2,2 ; 2,2 ; 2,2
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordSHIFT-REAGENT ; NMR ENANTIODISCRIMINATION ; STRUCTURALLY SIMPLE ; ALPHA-HYDROXY ; RECEPTOR ; RECOGNITION ; DISCRIMINATION ; DERIVATIVES ; MACROCYCLES ; ENANTIOMERS
AbstractA 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.
Language英语
Funding Organization2,2 ; 2,2 ; 2,2 ; 2,2
URL查看原文
WOS IDWOS:000330159500021
Citation statistics
Cited Times:29[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/119415
Collection中国科学院大连化学物理研究所
Corresponding AuthorLing Song
Affiliation1.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
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.,...&Ling Song.(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.
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