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Synthesis of the 4-Picoline (4-Pic) Complex of 4-Trifluoromethylphenylboronic Acid Catechol Ester (TFCB): The Unusual Co-crystal Structure—5(4-Pic·TFCB)·4-Pic

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Abstract

A novel complex of 4-picoline (4-Pic) with 4-trifluoromethylphenyl catechol boronate (TFCB) has been prepared and characterized by 1H NMR, 13C NMR, and X-ray diffraction analysis. When crystallized by evaporation from toluene a remarkable co-crystal was formed: 5(4-Pic·TFCB)·4-Pic (monoclinic P21, a = 13.4536(2) Å, b = 24.4320(3) Å, c = 14.0960(2) Å, β = 96.4340(10)°, vol. = 4604.15(11) Å3, Z = 2). The likely cause of the co-crystallization is π-stacking between complexed and free 4-Pic.

Graphical Abstract

A novel picoline-boronate complex has been prepared and characterized by 1H NMR, 13C NMR, and X-ray diffraction analysis. The solid-state structure of this simple complex reveals a remarkable co-crystal of 5(4-Pic·TFCB)·4-Pic.

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Acknowledgments

NJW and WRK would like to thank the Department of Chemistry & Physics at Western Carolina University. RDP would like to acknowledge the support of NSF (CHE-0443345) and the College of William and Mary for the purchase of X-ray equipment.

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Authors and Affiliations

  1. Department of Chemistry & Physics, Western Carolina University, Cullowhee, NC, 28723, USA

    Nicholas J. Wilcox & William R. Kwochka

  2. Chemistry Department, The College of William and Mary, PO Box 8795, Williamsburg, VA, 23187-8795, USA

    Robert D. Pike

Authors
  1. Nicholas J. Wilcox
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  2. William R. Kwochka
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  3. Robert D. Pike
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Correspondence to William R. Kwochka or Robert D. Pike.

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Wilcox, N.J., Kwochka, W.R. & Pike, R.D. Synthesis of the 4-Picoline (4-Pic) Complex of 4-Trifluoromethylphenylboronic Acid Catechol Ester (TFCB): The Unusual Co-crystal Structure—5(4-Pic·TFCB)·4-Pic. J Chem Crystallogr 46, 28–33 (2016). https://doi.org/10.1007/s10870-015-0624-9

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  • DOI: https://doi.org/10.1007/s10870-015-0624-9

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