Absolute Configurational Studies of Arylalkylamines by Circular Dichroism Measurements and Gas Chromatography

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The absolute configurations of twelve α-aryl and α, β-diarylalkylamines were studied as N-acyl derivatives by circular dichroism (CD) measurements and by gas Chromatography (GC). The signs of Cotton effects for the S-configuration around 260 nm were positive and those around 210nm were negative, although some exceptions were found due to the substituents on the benzene nuclei. In contrast, the GC behavior was considered less sensitive to the substituents on the benzene nuclei, and the elution orders were an R-before S-configuration consistently on a chiral OA-300 column. The absolute configurations of some amines were estimated in this study. GC as well as CD measurements could be a promising method for the assignment of the absolute configuration.
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