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Crystal structures of crown ethers containing an alkyl diarylphosphinate or a diarylphosphinic acid unit

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Abstract

This paper describes the structures of pseudo-18-crown-6 compounds (2, R,R-4 and 5) in the crystals together with theoretical calculations of the electronic circular dichroism (ECD) spectra. The achiral macrocyclic phosphinic acid 5 forms hydrogen-bonded dimers in the crystal. The O1–O2 distance (2.489 Ǻ) indicates strong H-bondings. The conformations of the macrorings of the achiral phosphinate 2 and the monomers of the achiral phosphinic acid 5 are chiral. A comparison of the torsion angles of the achiral methyl phosphinate 2 and the monomeric units of achiral 5 indicates a similar geometry. The torsion angles of the chiral methyl phosphinate (R,R)-4 differ more significantly from those in achiral methyl phosphinate 2. A negative 1Bb exciton couplet was observed in the ECD spectrum of monomeric (R,R)-6 in MeOH and H2O as in the spectra of (R,R)-4 in all solvents. To support the idea that (R,R)-4 has basically the same conformation in the crystal and in solution, the ECD spectrum of (R,R)-4 was calculated using the geometry of the molecule in the crystal. The calculated ECD spectrum shows a reasonable agreement with the ECD spectra obtained in solution. This shows that the steric structure observed in the crystal is predominant in solution as well.

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Acknowledgements

This work was supported by the Hungarian Scientific Research Fund (OTKA K62654 to P.H., PD71817 to V.F., PD71910 to T.T. and NI68466 to M.H.) and GVOP-3.2.1-2004-04-0345/3.0. The HPC Group computer facility, University of Szeged was used for several computations.

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Authors and Affiliations

  1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, P.O.B. 91, 1521, Budapest, Hungary

    György Székely & Péter Huszthy

  2. Laboratory for Chiroptical Structure Analysis, Institute of Chemistry, Eötvös Loránd University, Budapest, Hungary

    Viktor Farkas & Miklós Hollósi

  3. Protein Modelling Group, Hungarian Academy of Sciences, Eötvös Loránd University, Budapest, Hungary

    Viktor Farkas

  4. Institute of Structural Chemistry, Chemical Research Center of the Hungarian Academy of Sciences, P.O.B. 17, 1525, Budapest, Hungary

    László Párkányi

  5. Research Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, P.O.B. 91, 1521, Budapest, Hungary

    Tünde Tóth & Péter Huszthy

Authors
  1. György Székely
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  2. Viktor Farkas
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  3. László Párkányi
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  4. Tünde Tóth
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  5. Miklós Hollósi
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  6. Péter Huszthy
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Correspondence to Péter Huszthy.

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Dedicated to Professor Károly Lempert on the occasion of his 85th birthday.

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Székely, G., Farkas, V., Párkányi, L. et al. Crystal structures of crown ethers containing an alkyl diarylphosphinate or a diarylphosphinic acid unit. Struct Chem 21, 277–282 (2010). https://doi.org/10.1007/s11224-010-9581-2

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  • DOI: https://doi.org/10.1007/s11224-010-9581-2

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