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Chiral Task-Specific Solvents for Mandelic Acid and Their Impact on Solution Thermodynamics and Crystallization Kinetics

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Tulashie,  S. K.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;
Otto-von-Guericke-Universität Magdeburg, External Organizations;

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von Langermann,  J.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

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Lorenz,  H.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

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Seidel-Morgenstern,  A.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;
Otto-von-Guericke-Universität Magdeburg, External Organizations;

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Citation

Tulashie, S. K., von Langermann, J., Lorenz, H., & Seidel-Morgenstern, A. (2011). Chiral Task-Specific Solvents for Mandelic Acid and Their Impact on Solution Thermodynamics and Crystallization Kinetics. Crystal Growth & Design, 11(1), 240-246. doi:10.1021/cg101179y.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0013-8CD9-0
Abstract
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]