Journal of Organic Chemistry 2012-06-01

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

Daniel P Iwaniuk, Kimberly Yearick-Spangler, Christian Wolf

Index: J. Org. Chem. 77(11) , 5203-8, (2012)

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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.