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Journal Article

Protonation sites and hydrogen bonding in mono-hydrobromidesalts of two N,4-diheteroaryl 2-aminothiazoles


Goddard,  Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Böck, D., Beuchel, A., Goddard, R., Richter, A., Imming, P., & Seidel, R. W. (2021). Protonation sites and hydrogen bonding in mono-hydrobromidesalts of two N,4-diheteroaryl 2-aminothiazoles. Structural Chemistry, 32(6), 989-996. doi:10.1007/s11224-021-01730-0.

Cite as: https://hdl.handle.net/21.11116/0000-0008-B30E-F
The synthesis and structural characterization of N-(6-methoxypyridin-3-yl)-4-(pyridin-2-yl)thiazol-2-amine mono-hydrobromide monohydrate (3) and N-(6-methoxypyridin-3-yl)-4-(pyrazin-2-yl)thiazol-2-amine mono-hydrobromide 0.35 methanol solvate (4) are reported. The crystal structures of 3 (monoclinic, space group P21/n, Z=4) and 4 (monoclinic, space group, C2/c, Z=8) feature N,4-diheteroaryl 2-aminothiazoles showing similar molecular conformations but different sites of protonation and thus distinctly different intermolecular hydrogen bonding patterns. In 3, Namine–H⋯Br,N+pyridine–H⋯Owater, and Owater–H⋯Br hydrogen bonds link protonated N-(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+methoxypyridine–H⋯Npyrazine hydrogen bonds result in hydrogen-bonded zigzag chains of protonated N-(6-methoxypyridin-3-yl)-4-(pyrazin-2-yl)thiazol-2-amine molecules in 4.