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

Böck, Denise; Beuchel, Andreas; Goddard, Richard; Richter, Adrian; Imming, Peter; Seidel, Rüdiger W.

doi:10.1007/s11224-021-01730-0

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

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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

Abstract

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, N_amine–H⋯Br⁻,N⁺_pyridine–H⋯O_water, and O_water–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⋯N_pyrazine 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.