The direct enantiomeric resolution of racemic 2-(1H-imidazole-1-yl)-1-naphthalene-2-yl)ethanol esters, 1-(naphthalene-2-yl)ethanol esters, and 1-(1-hydroxynaphthalene-2-yl)-2-(1H-imidazole-1-yl)ethanol on silica-based cellulose tris(3,5-dimethylphenylcarbamate) (Chiralcel OD) column is described. The separations were performed using mobile phases which consist of alcohol (methanol, ethanol or 2-propanol)/n-hexane in various proportions. The effect of structural features of the solutes along with the nature and concentration of alcohol in the mobile phase on the discrimination between the enantiomers was examined for different mobile phase compositions. The results suggest that not only the structure and concentration of alcohol in the mobile phase, but also the subtle structural differences in racemates can have a pronounced effect on enantiomeric separation and retention. Baseline separations were obtained for 2-(1H-imidazole-1-yl)-1-naphthalene-2-yl)ethanol esters carrying imidazole ring in addition to ester functional group in their structures. The alpha values of the resolved enantiomers of 2-(1H-imidazole-1-yl)-1-naphthalene-2-yl)ethanol esters were in the range of 1.49-1.62 while the R (s) values varied from 4.20 to 6.75 when methanol/n-hexane (70:30 v/v) was used as mobile phase.