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Resolution of 1,1′-Binaphthyl-2,2′-Dicarboxylic Acid with Quinine: Structure of the Intermediate (S)-1,1′-Binaphthyl-2,2′-Dicarboxylate Dihydrate Diastereomeric Salt

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Abstract

Racemic 1,1′-binaphthyl-2,2′-dicarboxylic acid (BNDA) was resolved using quinine as the resolving agent. The structure of the resultant quininium (S)-1,1′-binaphthyl-2,2′-dicarboxylate dihydrate salt (1) was elucidated. The asymmetric unit contained one 1,1′-binaphthyl-2,2′-dicarboxylate anion, two quininium cations and two water molecules. The structure was solved successfully in the orthorhombic space group P212121 with unit cell dimensions: a = 11.100(2) Å, b = 16.572(3) Å, c = 28.726(6) Å.

Graphical Abstract

Racemic 1,1′-binaphthyl-2,2′-dicarboxylic acid (BNDA) was resolved using quinine as the resolving agent. The structure of the resultant quininium (S)-1,1′-binaphthyl-2,2′-dicarboxylate dihydrate salt (1) was elucidated.

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Acknowledgments

We thank the CPUT and the NRF (Pretoria) for funding.

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Authors and Affiliations

  1. Department of Chemistry, Cape Town Campus, Cape Peninsula University of Technology, P.O Box 652, Cape Town, 8000, South Africa

    Ayesha Jacobs, Luigi R. Nassimbeni & Amina Sayed

  2. Institut für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Strasse 29, 09596, Freiberg, Germany

    Edwin Weber

Authors
  1. Ayesha Jacobs
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  2. Luigi R. Nassimbeni
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  3. Amina Sayed
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  4. Edwin Weber
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Correspondence to Ayesha Jacobs.

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Jacobs, A., Nassimbeni, L.R., Sayed, A. et al. Resolution of 1,1′-Binaphthyl-2,2′-Dicarboxylic Acid with Quinine: Structure of the Intermediate (S)-1,1′-Binaphthyl-2,2′-Dicarboxylate Dihydrate Diastereomeric Salt. J Chem Crystallogr 41, 854–857 (2011). https://doi.org/10.1007/s10870-011-0012-z

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  • DOI: https://doi.org/10.1007/s10870-011-0012-z

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