• Medientyp: E-Artikel
  • Titel: Protonation sites and hydrogen bonding in mono-hydrobromide salts of two N,4-diheteroaryl 2-aminothiazoles
  • Beteiligte: Böck, Denise; Beuchel, Andreas; Goddard, Richard; Richter, Adrian; Imming, Peter; Seidel, Rüdiger W.
  • Erschienen: Springer Science and Business Media LLC, 2021
  • Erschienen in: Structural Chemistry
  • Sprache: Englisch
  • DOI: 10.1007/s11224-021-01730-0
  • ISSN: 1040-0400; 1572-9001
  • Schlagwörter: Physical and Theoretical Chemistry ; Condensed Matter Physics
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  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>The synthesis and structural characterization of <jats:italic>N</jats:italic>-(6-methoxypyridin-3-yl)-4-(pyridin-2-yl)thiazol-2-amine mono-hydrobromide monohydrate (<jats:bold>3</jats:bold>) and <jats:italic>N</jats:italic>-(6-methoxypyridin-3-yl)-4-(pyrazin-2-yl)thiazol-2-amine mono-hydrobromide 0.35 methanol solvate (<jats:bold>4</jats:bold>) are reported. The crystal structures of <jats:bold>3</jats:bold> (monoclinic, space group <jats:italic>P</jats:italic>2<jats:sub>1</jats:sub>/<jats:italic>n</jats:italic>, <jats:italic>Z</jats:italic> = 4) and <jats:bold>4</jats:bold> (monoclinic, space group, <jats:italic>C</jats:italic>2/<jats:italic>c</jats:italic>, <jats:italic>Z</jats:italic> = 8) feature <jats:italic>N</jats:italic>,4-diheteroaryl 2-aminothiazoles showing similar molecular conformations but different sites of protonation and thus distinctly different intermolecular hydrogen bonding patterns. In <jats:bold>3</jats:bold>, N<jats:sub>amine</jats:sub>–H⋯Br<jats:sup>−</jats:sup>, N<jats:sup>+</jats:sup><jats:sub>pyridine</jats:sub>–H⋯O<jats:sub>water</jats:sub>, and O<jats:sub>water</jats:sub>–H⋯Br<jats:sup>−</jats:sup> hydrogen bonds link protonated <jats:italic>N</jats:italic>-(6-methoxypyridin-3-yl)-4-(pyridin-2-yl)thiazol-2-amine and water molecules and bromide anions into a three-dimensional hydrogen-bonded network, whereas intermolecular N<jats:sup>+</jats:sup><jats:sub>methoxypyridine</jats:sub>–H⋯N<jats:sub>pyrazine</jats:sub> hydrogen bonds result in hydrogen-bonded zigzag chains of protonated <jats:italic>N</jats:italic>-(6-methoxypyridin-3-yl)-4-(pyrazin-2-yl)thiazol-2-amine molecules in <jats:bold>4</jats:bold>.</jats:p>