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  • Chem Sci Trans., 2016, 5(3),  pp 727-733  

    DOI:10.7598/cst2016.1246

    Research Article

    A Novel Method of Diastereomeric Resolution of R-Phenyl Alanine-S-Mandelate from the Racemic Mixture

  • USHA S* and CHARLES KANAKAM CHRISTOPHER
  • Department of Chemistry, Sri Sairam Engineering College, Chennai-600044, India
    Department of Chemistry, Presidency College, Chennai-600005, India
  • Abstract

    The diastereomeric separation of racemic mixture of (R,S) mandelic acid using R-Phenyl alanine was carried out using the hydrolysis of the amino acid complex bis-L-phenyl alanine mandelate (BLPAMA), by refluxing with methanol. Resultant clear solution was allowed for slow evaporation and obtained the diastereomeric crystalline material R-Phenyl alanine-S-mandelate (RPASMA), homogenous on TLC and having sharp melting point. The purity of diastereomer was confirmed by the characteristic studies, thermal study and single crystal XRD study. The inter molecular and intra molecular hydrogen bonding present in the title compound, the high thermal stability and the presence of non- centerosymmetric space group C2 indicates the compound can be used for optical device applications. The title compound showed second harmonic generation (SHG) and NLO activity twice that of standard KDP. The optical rotation and mass spectral analysis confirms the isolation of novel diastereomer.

    Keywords

    BLPAMA, RPASMA, Diastereomeric isolation, SHG, NLO activity

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