Resolution of α-halogenocarboxylic acids by gas chromatography on (r)-n-lauroyl-α-(1-naphtyl)ethylamine

Add time:08/12/2019    Source:sciencedirect.com

α-Fluoro-, α-chloro and α-bromo C3-C6 carboxylic acids were separated efficiently into their enantiomers, after conversion into tert.-butylamides, on a whiskerwalled glass capillary column (40 m x 3.5 mm I.D.) coated with (R)-N-lauroyl-α-(1-napththyl)ethylamine. The resolution coefficient (α) of the derivatives of the α-F, α-Cl and α-Br acids were 1.04, 1.05-1.08 and 1.08-1.13, respectively, at 100°C. The retention indices (I) and differential Gibb's free energies of solution ▵(▵G) were calculated and both were found to increase for the acids in the order F < Cl < Br, i.e. in the same order as the C-X covalent radii. The order of emergence was found to be R- after the S-solute on the R-phase. An intercalation model to interpret the stereoselective solute-solvent interactions is proposed.

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