Hydrogen-bonded helices in 2-aminothiazole derivatives: generation of chiral crystals from small achiral molecules

The hydrobromide and nitrate of 4-(tert-butyl)-5-(4-chlorobenzyl)thiazol-2-amine have been synthesized, and their chiral symmetry breaking in the solid-state has been investigated. It is shown that each molecule is connected by continuous N–H···Br/N–H···O hydrogen bonds to afford left- or right-handed helical assemblies in the crystal packing. Mirror-image CD spectra were obtained for the right- and left-handed helical-type chiral crystals.

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