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Chiral trans-1,2-diaminocyclohexane derivatives as chiral solvating agents for carboxylic acids

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An Erratum to this article was published on 01 May 2011

Abstract

Efficient use of the readily accessible chiral C 2-symmetric acyclic diamines (1–2) as well as macrocyclic amines (3–5) containing trans-1,2-diaminocyclohexyl moiety as chiral solvating agents (CSA) for the determination of enantiomeric excess of representative carboxylic acids (6–7) and an amino acid derivative (8) is illustrated. The enantiomeric composition of different carboxylic acids estimated here by the 1H NMR method, based on the integration of the corresponding methine proton signals are in good correlation with that determined using HPLC method. The data are in accordance with the formation of multimolecular diastereomeric complexes in solution, which render good splitting of NMR signals for the enantiomers of representative carboxylic acids as well as for N-Ts-phenylglycine (up to ΔΔδ = 0.295 ppm, 118 Hz).

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Authors and Affiliations

  1. School of Chemistry, University of Hyderabad, Central University P.O., Hyderabad, 500 046, India

    Mariappan Periasamy, Manasi Dalai & Meduri Padmaja

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  1. Mariappan Periasamy
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  2. Manasi Dalai
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  3. Meduri Padmaja
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Correspondence to Mariappan Periasamy.

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An erratum to this article can be found at http://dx.doi.org/10.1007/s12039-011-0144-x

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Periasamy, M., Dalai, M. & Padmaja, M. Chiral trans-1,2-diaminocyclohexane derivatives as chiral solvating agents for carboxylic acids. J Chem Sci 122, 561–569 (2010). https://doi.org/10.1007/s12039-010-0090-z

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