A Simple Method for the Determination of Enantiomeric Excess and identity of Chiral Carboxylic Acids

被引：148

作者：

Joyce, Leo A. ^{[2
]}

Maynor, Marc S. ^{[2
]}

Dragna, Justin M. ^{[2
]}

da Cruz, Gabriella M. ^{[2
]}

Lynch, Vincent M. ^{[2
]}

Canary, James W. ^{[1
]}

Anslyn, Eric V. ^{[2
]}

机构：

[1] NYU, Dept Chem, New York, NY 10003 USA

[2] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 34期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

COUPLED CIRCULAR-DICHROISM; ABSOLUTE CONFIGURATIONAL ASSIGNMENT; INDICATOR-DISPLACEMENT ASSAYS; TRIPODAL TETRADENTATE LIGANDS; ALPHA-AMINO-ACIDS; CU(II) COMPLEXES; METAL-COMPLEXES; ALCOHOLS; DISCRIMINATION; IDENTIFICATION;

D O I：

10.1021/ja205775g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The association between an achiral copper(II) host (1) and chiral carboxylate guests was studied using exciton-coupled circular dichroism (ECCD). Enantiomeric complexes were created upon binding of the enantiomers of the carboxylate guests to the host, and the sign of the resultant CD signal allowed for determination of the configuration of the studied guest. The difference in magnitudes and shapes of the CD signals, in conjunction to be determined successfully. A model was created for the host-guest complexes which successfully predicts the sign of the observed CD signal. Further, Taft parameters were used in the model, leading to rationalization of the observed magnitudes of the CD signals. Finally, the enantiomeric excess (ee) of unknown samples of three chiral carboxylic acid guests was determined with an average absolute error of +/- 3.0%.

引用

页码：13746 / 13752

页数：7

共 63 条

[1] Application of electronic circular dichroism in configurational and conformational analysis of organic compounds [J].