Four kinds of cellulose derivatives, including two regioselectively substituted cellulose esters (6-O-acetyl-2,3-di-O-benzoyl cellulose and 2,3-di-O-acetyl-6-O-benzoyl cellulose), were synthesized so that the effects of their functional group distribution on their chiral discrimination ability could be examined. The degree of substitution by functional groups appeared to have a critical effect on the separation in most cases, but the type of the functional group at the C-6 position also significantly influenced chiral discrimination when a series of neutral arylalcohol derivatives were used as racemates, Chirality 12:670-674, 2000. (C) 2000 Wiley-Liss, Inc.