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Separation of (S)-(−)-3-Methyl-2-pyrrolidinone as an Inclusion Complex with (R)-(+)-4,4′,6,6′-Tetrachloro-2,2′-bis(hydroxydiphenylmethyl)-1,1′-biphenyl Host and its X-ray Structural Study

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Abstract

By inclusion complexation with the chiral host compound (R)-(+)-4,4′,6,6′-tetrachloro-2,2′-bis(hydroxydiphenylmethyl)-1,1′-biphenyl, racemic 3-methyl-2-pyrrolidinone was resolved and its (S)-(−)-enantiomer was isolated as a 1:1 inclusion complex, which crystallises in the orthorhombic crystal system in the space group P212121 (a = 14.1163(2) Å, b = 14.7140(3) Å, c = 17.2025(3) Å). By the inclusion complexation, the keto–enol equilibrium of the guest was frozen and the keto-form was isolated in a pure form. By X-ray structural study of the complex, the guest molecule included was elucidated to be the keto-form and its absolute configuration was determined to be (S).

Index Abstract

By inclusion complexation with (R)-(+)-4,4′,6,6′-tetrachloro-2,2′-bis (hydroxydiphenylmethyl)-biphenyl, racemic 3-methyl-2-pyrrolidinone was resolved and its (S)-(−)-enantiomer isolated and in addition the keto–enol equilibrium of the guest was frozen and the keto-form isolated.

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Authors and Affiliations

  1. Department of Chemistry, University of Stellenbosch, Matieland, 7602, South Africa

    Tanya le Roex

  2. Department of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa

    Luigi R. Nassimbeni

  3. Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Riaicho, Okayama, 700-0005, Japan

    Fumio Toda

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  1. Tanya le Roex
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  2. Luigi R. Nassimbeni
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  3. Fumio Toda
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Correspondence to Tanya le Roex.

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le Roex, T., Nassimbeni, L.R. & Toda, F. Separation of (S)-(−)-3-Methyl-2-pyrrolidinone as an Inclusion Complex with (R)-(+)-4,4′,6,6′-Tetrachloro-2,2′-bis(hydroxydiphenylmethyl)-1,1′-biphenyl Host and its X-ray Structural Study . J Chem Crystallogr 38, 77–79 (2008). https://doi.org/10.1007/s10870-007-9312-8

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