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LFER and CoMFA studies on optical resolution of α-alkyl α-aryloxy acetic acid methyl esters on DACH-DNB chiral stationary phase

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Summary

The HPLC resolution of a series of racemic α-substituted α-aryloxy acetic acid methyl esters I on a π-acid chiral stationary phase containing N,N′-(3,5-dinitrobenzoyl)-trans-1,2-diaminocyclohexane as chiral selector was modelled by linear free energy-related (LFER) equations and comparative molecular field analysis (CoMFA). Our results indicate that the retention process mainly depends on solute lipophilicity and steric properties, whereas enantioselectivity is primarily influenced by electrostatic and steric interactions. CoMFA provided additional information with respect to the LFER study, allowed the mixing of different subsets of I and led to a quantitative 3D model of steric and electrostatic factors responsible for chiral recognition.

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Authors and Affiliations

  1. Dipartimento Farmacochimico, Università degli Studi di Bari, via E. Orabona 4, I-70126, Bari, Italy

    Angelo Carotti, Cosimo Altomare, Saverio Cellamare, Giancarlo Bettoni, Fulvio Loiodice, Nicola Tangari & Vincenzo Tortorella

  2. Dipartimento Farmacochimico, Università di Messina, I-90168, Messina, Italy

    AnnaMaria Monforte

Authors
  1. Angelo Carotti
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  2. Cosimo Altomare
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  3. Saverio Cellamare
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  4. AnnaMaria Monforte
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  5. Giancarlo Bettoni
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  6. Fulvio Loiodice
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  7. Nicola Tangari
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  8. Vincenzo Tortorella
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Carotti, A., Altomare, C., Cellamare, S. et al. LFER and CoMFA studies on optical resolution of α-alkyl α-aryloxy acetic acid methyl esters on DACH-DNB chiral stationary phase. J Computer-Aided Mol Des 9, 131–138 (1995). https://doi.org/10.1007/BF00124403

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  • DOI: https://doi.org/10.1007/BF00124403

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