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

作者:Joyce Leo A; Maynor Marc S; Dragna Justin M; da Cruz Gabriella M; Lynch Vincent M; Canary James W*; Anslyn Eric V
来源:Journal of the American Chemical Society, 2011, 133(34): 13746-13752.
DOI:10.1021/ja205775g

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%.

  • 出版日期2011-8-31