The hydrogen-bonding networks of 2-amino-4-phenyl-1,3-thiazole derivatives

Aromatic/Proaromatic Donors in 2‐Dicyanomethylenethiazole Merocyanines: From Neutral to Strongly Zwitterionic Nonlinear Optical Chromophores

“…The steric hindrance between the substituent at 5-position of the thiazole ring and the phenyl group might be the origin of such a large dihedral angle, because in 5-unsubstituted 4-phenylthiazoles the rings are essentially coplanar, [26] whereas this is not the case for their 5-substituted analogues. [27] Notably, the packing in the crystal is polar (in keeping with the space group, P2 1 ), meaning that this material will show bulk NLO activity. For the asymmetric unit and absolute structure reported, the molecules are aligned in such a way that all of the acceptor groups point to the positive direction of the b axis, and the donor fragments all point to negative b.…”

4-(4-Chlorophenyl)-N-[(E)-4-(dimethylamino)benzylidene]-1,3-thiazol-2-amine

“…For related structures, see: Lynch et al (1999;2002). For medicinal applications of thiazole derivatives, see: Misra et al (2004).…”

“…The title compound, C 18 H 16 ClN 3 S, (I), is a 2-amino-thiazole derivative. Few structures of such derivatives have been determined (Lynch et al, 1999;2002) and some of them have been shown to act as inhibitor of cyclin-dependent kinase (Misra et al, 2004). The structure of (I) with adopted atom-numbering scheme is shown in Fig 1. (I) adopts an extended structure.…”

2-Amino-4-(4-chloro-3-methylphenyl)-5-propyl-1,3-thiazolium iodide

“…There are two additional compounds that have a naphthyl group instead of the benzene ring. Most of these structures were analyzed in terms of hydrogen-bonding networks, because the 2-amino-1,3-thiazole group can be a donor for two and an acceptor for three hydrogen bonds (Lynch et al, 2002;Lynch & McClenaghan, 2004).…”

“…However, the compound with the smallest twist between the rings has a hydroxyl group in the ortho position (XUNKEW). In this case the intramolecular hydrogen bond between the hydroxy group and the N atom from the 1,3-thiazole ring causes the molecule to be almost planar (Lynch et al, 2002).…”