Homochiral and Heterochiral Polyesters: Polymers Derived from Mandelic Acid

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The kinetics of polymerization of racemic and optically active mandelic acid were determined under a variety of conditions. The initial rate of monomer consumption in the reaction with racemic mandelic acid was approximately twice that for the single enantiomer for acid-catalyzed reactions in benzene solution. A significant increase in the rate of consumption of monomer was observed in the reaction of optically active mandelic acid coincident with the formation of the cyclic dimer (mandelide). The structure of the dimer formed from a single enantiomer of mandelic acid was determined by single-crystal X-ray analysis. These observations are consistent with a scheme where the rate of chain extension of dimeric and higher species is greater than that for the formation of dimers and where the cyclic dimer is derived from trimeric and higher species and not from the noncyclic dimer. © 1990, American Chemical Society. All rights reserved.

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Chemistry of Materials

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