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The synthesis and application of enantiopure short-chain mandelic acid esters as chiral task-specific solvents were investigated for the determination of hetereochiral interactions between chiral solutes and chiral solvents. Because of specific chiral interactions between the mandelic acid enantiomers as solutes and the S-configured solvents for this chiral system, asymmetric behavior was elucidated. Differences for (R)- and (S)-mandelic acid were determined with respect to solution thermodynamics and crystallization kinetics for the chiral solvents (S)-mandelic acid n-propyl ester [(S)-n-propyl mandelate] and (S)-mandelic acid isopropyl ester [(S)-isopropyl mandelate]. These differences were explained via evaluation of enantiospecific interactions applying molecular modeling methods.
copyright American Chemical Society [accessed November 19th, 2010]
