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Structural characterization of the crystalline diastereomeric complexes of enantiopure dimethylacridino-18-crown-6 ether and the enantiomers of 1-(1-naphthyl)ethylamine hydrogen perchlorate

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Abstract

This paper describes the X-ray crystal structure of the diastereomeric complexes formed by enantiopure dimethyl-substituted acridino-18-crown-6 ether (R,R)-1 and the enantiomers of 1-(1-naphthyl)ethylammonium perchlorate. We found that the heterochiral complex (R,R)-1–(S)-1-NEA is more stable than the homochiral one (R,R)-1–(R)-1-NEA. In the case of the heterochiral complex, the X-ray studies revealed a strong intermolecular π–π interaction between the naphthyl unit and the acridine moiety. However, in the case of the homochiral complex, π–π interaction was not found. We suggest that the existence or absence of the π–π interaction and the difference in steric repulsions in the diastereomers is responsible for the enantiomeric discrimination.

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Acknowledgments

Financial supports of the Hungarian Scientific Research Fund (OTKA K112289, K109486 and NK84008), the CRP/HUN14-01 ICGEB Research Grant, the New Széchenyi Development Plan (TÁMOP-4.2.1/B-09/1/KMR-2010-0002) and the Pro Progressio Foundation are gratefully acknowledged.

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Authors and Affiliations

  1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, PO Box 91, Budapest, 1521, Hungary

    Tünde Tóth, Tamás Németh & Péter Huszthy

  2. Department of Applied Biotechnology and Food Sciences, Budapest University of Technology and Economics, Budapest, Hungary

    Ibolya Leveles & Beáta G. Vértessy

  3. Institute of Enzymology, RCNS, Hungarian Academy of Sciences, Budapest, Hungary

    Beáta G. Vértessy

Authors
  1. Tünde Tóth
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  2. Tamás Németh
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  3. Ibolya Leveles
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  4. Beáta G. Vértessy
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  5. Péter Huszthy
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Correspondence to Péter Huszthy.

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Dedicated to Professor George A. Oláh on the occasion of his 90th birthday.

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Tóth, T., Németh, T., Leveles, I. et al. Structural characterization of the crystalline diastereomeric complexes of enantiopure dimethylacridino-18-crown-6 ether and the enantiomers of 1-(1-naphthyl)ethylamine hydrogen perchlorate. Struct Chem 28, 289–296 (2017). https://doi.org/10.1007/s11224-016-0818-6

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  • DOI: https://doi.org/10.1007/s11224-016-0818-6

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