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4-Chloro-2,6-bis(hydroxymethyl)pyridinium Chloride and 4-Dimethylamino-2,6-bis(hydroxymethyl)pyridinium Chloride Hemihydrate

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Abstract

Two substituted pyridinium chloride salts, namely 4-chloro-2,6-bis(hydroxymethyl)pyridinium chloride (triclinic, P-1, a = 6.0651(8) Å, b = 8.4393(8) Å, c = 8.6554(9) Å, α = 78.845(1)°, β = 83.156(1)°, γ = 89.047(1)°; V = 431.55(8) Å3; Z = 2) and 4-dimethylamino-2,6-bis(hydroxymethyl)pyridinium chloride hemihydrate (orthorhombic, Aba2, a = 17.2179(14) Å, b = 17.6332(15) Å, c = 7.2068(6) Å; V = 2188.0(3) Å3; Z = 4), have been structurally characterized. Hydrogen bonding and van der Waals contacts are evident in both structures. Furthermore, the 4-dimethylamino derivative features a trigonal planar dimethylamino group with some π interaction between the nitrogen atom and the pyridine ring.

Graphical Abstract

Two compounds, namely 4-chloro-2,6-bis(hydroxymethyl)pyridinium chloride and 4-dimethylamino-2,6-bis(hydroxymethyl)pyridinium chloride hemihydrate, have been spectroscopically and structurally characterized.

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Acknowledgments

We thank the Department of Chemistry & Biochemistry at the University of Alaska Fairbanks for financial support, and the National Science Foundation for their support (DUE-9850731) in the purchase of the 300 MHz NMR spectrometer that made this study possible. The authors also thank everyone involved in the 2007 Crystallography Summer School at the University of California San Diego; the instructors (Drs. Charles Campana, Antonio DiPasquale, Bruce Foxman, James Golen, Scott Kassel, Arnold Rheingold, Richard Staples, Kraig Wheeler, Paul Williard) patiently guided the authors through all the stages of obtaining the X-ray structures reported herein.

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Authors and Affiliations

  1. Department of Chemistry & Biochemistry, University of Alaska Fairbanks, 900 Yukon Drive, Fairbanks, AK, 99775-6160, USA

    Zachary N. Pickett & William A. Howard

  2. Los Alamos National Laboratory, Mail Stop J514, Los Alamos, NM, 87545, USA

    Christopher R. Graves

Authors
  1. Zachary N. Pickett
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  2. William A. Howard
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  3. Christopher R. Graves
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Correspondence to William A. Howard.

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Pickett, Z.N., Howard, W.A. & Graves, C.R. 4-Chloro-2,6-bis(hydroxymethyl)pyridinium Chloride and 4-Dimethylamino-2,6-bis(hydroxymethyl)pyridinium Chloride Hemihydrate. J Chem Crystallogr 38, 717–721 (2008). https://doi.org/10.1007/s10870-008-9439-2

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  • DOI: https://doi.org/10.1007/s10870-008-9439-2

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