Stereoselective UV sensing of 1,2-diaminocyclohexane isomers based on ligand displacement with a diacridylnaphthalene N,N'-dioxide scandium complex

The Journal of Organic Chemistry
Daniel P IwaniukChristian Wolf

Abstract

Stereoselective displacement of diacridylnaphthalene N,N'-dioxide ligands, 1, from a scandium(III) complex can be used for quantitative detection of 1,2-diaminocyclohexane isomers. The diastereoselective sensing assay with Sc(syn-1)(2) shows excellent linearity between the sample de and the measured UV absorption change, and sensing of mixtures comprising both low and high de values gave results within 5% accuracy. All three stereoisomers of 1,2-diaminocyclohexane can be differentiated using Sc[anti-(-)-1](2) in the same ligand displacement assay.

References

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Apr 13, 2002·The Journal of Organic Chemistry·Christian Wolf, Pili A Hawes
Apr 25, 2002·Journal of the American Chemical Society·Suk Joong Lee, Wenbin Lin
Jun 29, 2004·Angewandte Chemie·Jianzhang ZhaoTony D James
Sep 16, 2004·Chemical Communications : Chem Comm·Xuefeng Mei, Christian Wolf
Nov 13, 2004·Journal of the American Chemical Society·Xuefeng Mei, Christian Wolf
Dec 9, 2004·Journal of the American Chemical Society·Jianzhang ZhaoTony D James
Mar 24, 2005·Journal of the American Chemical Society·Lei ZhuEric V Anslyn
Aug 27, 2005·Organic Letters·Gilbert E Tumambac, Christian Wolf
Apr 28, 2006·Journal of the American Chemical Society·J Frantz Folmer-AndersenEric V Anslyn
May 6, 2008·The Journal of Organic Chemistry·Shuanglong LiuChristian Wolf
Aug 22, 2008·Journal of the American Chemical Society·Diana LeungEric V Anslyn
Dec 31, 2008·Angewandte Chemie·Tummanapalli SatyanarayanaHenri B Kagan
Dec 3, 2010·Journal of the American Chemical Society·Shanshan Yu, Lin Pu

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Citations

Oct 5, 2016·Journal of the American Chemical Society·Zeus A De Los Santos, Christian Wolf
Jun 14, 2017·Journal of the American Chemical Society·Li-Li WangWei Jiang
Oct 16, 2012·Chemical Communications : Chem Comm·Daniel P Iwaniuk, Christian Wolf
Feb 7, 2014·Chemical Reviews·Xin ZhangJuyoung Yoon

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