Chromatographic investigations of the configurational and geometrical isomerism of allylic N-terpenyl-N-hydroxyethyl-nitrosamines

S. L. Abidi

doi:10.1016/s0021-9673(01)93707-0

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Chromatographic investigations of the configurational and geometrical isomerism of allylic N-terpenyl-N-hydroxyethyl-nitrosamines

S. L. Abidi

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Abstract

A preparative adsorption column chromatographic method is reported for the separation of cis and trans geometrical isomers of two types of N-nitrosamines derived from allylic terpenyl ethanolamines (experimental fish toxicants). Column eluates were monitored by gas chromatography in which a Carbowax 20M stationary phase was used. Further separation of E and Z configurational isomers was achieved by reversed-phase and normal-phase high-performance liquid chromatography. In the reversed-phase high-performance liquid chromatography system (acetonitrilewater), the 6′,7′-acetylenic nitrosamines (NMOA) were efficiently resolved by using an argentous (AgNO 3 ) mobile phase, whereas the presence of sodium alkanesulfonate in the aqueous acetonitrile mobile phase favored the base-line resolution of the 6′,7′-olefinic nitrosamines (NDOA). For normal-phase separation on a silica column, addition of tetrahydrofuran to the mobile phase (methylene chloride-2-propanol) resulted in a varying degree of improvement in peak resolution ( R ) and column selectivity (α). Effects of temperature on the chromatographic behavior of the nitrosamine components are described. The high-performance liquid chromatographic separation method has proved to be applicable for the trace analysis of the title nitrosamines in organic tissues by way of thermal energy analysis.

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S. L. Abidi. 1984. Chromatographic investigations of the configurational and geometrical isomerism of allylic N-terpenyl-N-hydroxyethyl-nitrosamines. https://doi.org/10.1016/s0021-9673(01)93707-0

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