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Insight Into the Conformational Arrangement of a Bis-THF Diol Compound Through 2D-NMR Studies and X-Ray Structural Analysis

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Abstract

The conformational arrangement of an all-threo bis-THF diol compound, synthesized through the RuO4-catalysed oxidative bis-cyclization of farnesyl acetate, was determined via crystallographic analysis and detailed 2D-NMR solution studies. The bis-THF compound crystallizes in the orthorhombic Pbca space group, with unit cell parameters a = 10.496(1), b = 17.974(1), c = 19.777(2) Å, Z = 8. The final refinement converged to R 1 = 0.0484 for 4714 independent observed reflections having I > 2σ(I). There is a good agreement between the solution molecular conformation determined by 2D-NMR and the X-ray molecular conformation. The molecule adopts a folded, horse shoe-type conformation both in solution and in the crystal, that suggests aptitude to coordinate cations. Additionally, in the crystals, the molecular conformation is stabilized by intramolecular and intermolecular H-bonding.

Graphical Abstract

2D-NMR and X-ray studies indicate that the bis-THF shown adopts a folded, horse shoe-type, conformation both in solution and in the crystal, that suggests aptitude to coordinate cations.

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Acknowledgments

The authors thank the Centro Interdipartimentale di Metodologie chimico Fisiche (CIMCF) of University of Naples “Federico II” for NMR and X-ray facilities.

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Authors and Affiliations

  1. Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli “Federico II”, Via Cynthia 4, 80126, Naples, Italy

    Vincenzo Piccialli & Sabrina Zaccaria

  2. Dipartimento di Chimica ‘‘Paolo Corradini’’, Università degli Studi di Napoli “Federico II”, Via Cynthia 4, 80126, Naples, Italy

    Roberto Centore & Angela Tuzi

  3. Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli “Federico II”, Via D. Montesano 49, 80131, Napoli, Italy

    Nicola Borbone, Giorgia Oliviero, Stefano D’Errico & Valentina D’Atri

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  1. Vincenzo Piccialli
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  2. Sabrina Zaccaria
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  3. Roberto Centore
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  4. Angela Tuzi
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  6. Giorgia Oliviero
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  7. Stefano D’Errico
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  8. Valentina D’Atri
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Correspondence to Vincenzo Piccialli or Roberto Centore.

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Piccialli, V., Zaccaria, S., Centore, R. et al. Insight Into the Conformational Arrangement of a Bis-THF Diol Compound Through 2D-NMR Studies and X-Ray Structural Analysis. J Chem Crystallogr 42, 360–365 (2012). https://doi.org/10.1007/s10870-011-0254-9

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  • DOI: https://doi.org/10.1007/s10870-011-0254-9

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