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Chiral Separations 1: How do our GC chiral columns compare?

17 Aug 2021

Predicting chiral separations is challenging. Using standard capillary columns, general predictions about separations can be made based on the solubility of compounds in different phases; however, chiral predictions are far more complicated.

To make this decision somewhat easier, we compiled resolution values for the enantiomers of 21 chiral compounds with different functional groups, such as terpenes, alcohols or lactones.

Compounds			Column Resolution Factors
			Rt-βDEX sm	Rt-βDEX se	Rt-βDEX sp	Rt-βDEX sa	Rt-βDEX cst	Rt-βDEX m
Terpenes	1	α-pinene	3.14	0.82	ns	ns	0.82	3.19
	2	limonene	5.60	8.05	1.22	ns	2.04	1.41
Alcohols	3	1-octen-3-ol	1.08	ns	ns	2.00	ns	ns
	4	linalool	3.10	5.96	1.79	1.60	2.25	1.01
	5	α-terpineol	4.72	5.20	1.29	2.82	2.69	1.54
	6	terpinen-4-ol	1.90	1.92	ns	2.47	ns	1.41
	7	isoborneol	3.76	3.35	ns	0.79	1.87t	2.15
	8	β-citronellol	0.80	0.89	ns	0.98	ns	ns
	9	menthol	1.24	1.24	1.07	0.93	0.89	1.58
	10	2,3-butanediol	6.44	7.10	1.46	2.61	1.27	2.43
	11	1-phenylethanol	7.52	6.52	ns	6.43	4.87	5.88
Ketones	12	camphor	1.70	2.13	0.50	4.20	2.22t	ns
	13	α-ionone	5.67	3.31	0.80	4.69	1.37	2.81
	14	menthone	0.59	5.76	ns	1.16	2.60	4.11
Lactones	15	γ-nonalactone	4.19	5.07	2.11	4.00	3.82	1.03
	16	γ-undecalactone	2.39	3.24	1.20	3.65	3.18	ns
	17	δ-decalactone	0.80	ns	ns	1.91	1.69	ns
	18	ethyl-2-methylbutyrate	3.94	4.66	ns	ns	ns	0.92
Esters	19	linalyl acetate	ns	2.36	ns	ns	ns	ns
	20	styrene oxide	4.53	10.77	2.86	2.26	1.16t	3.03
Epoxides	21	trans-linalool oxide	9.71	2.96	ns	1.20	3.02t	7.44
	21	cis-linalool oxide	6.06	4.28	ns	0.91	2.19t	4.38