4-(4-Bromophenyl)thiazol-2-amine: Crystal structure determination, DFT calculations, visualizing intermolecular interactions using Hirshfeld surface analysis, and DNA binding studies

Channar P. A. , Arshad N., Larik F. A. , Farooqi S. I. , Saeed A., HÖKELEK T., ...More

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, vol.32, no.9, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 32 Issue: 9
  • Publication Date: 2019
  • Doi Number: 10.1002/poc.3968
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Hacettepe University Affiliated: Yes


2-Aminothiazole is a valuable synthon in organic synthesis and an important structural unit of pharmaceutically active drugs. It is accessible via several synthetic routes. In the current account, compound 4 {4-(4-bromophenyl) thiazol-2-amine} was synthesized by employing a recently reported procedure of Gabriel synthesis using Lawesson reagent. The title compound was characterized through spectro-elemental analytical data, and its crystal structure was determined by single-crystal X-ray diffraction. The torsion angles, bond lengths, and bond strengths between the planes of the thiazole and phenyl rings were optimized by theoretical calculations by applying the B3LYP/6-311++G(d,p) level for the purpose of investigating the conformational effects on the stabilization of the crystal packing. HOMO-LUMO analysis, vibrational analysis, and thermodynamic parameters were also investigated. A detailed analysis of the intermolecular interactions of thiazole moiety bearing the amino and bromophenyl ring has been performed based on the Hirshfeld surfaces and their associated two-dimensional fingerprint plots. The relative contributions of the main intermolecular contacts as well as the enrichment ratios derived from the Hirshfeld surface analysis establish the 2-aminothiazole synthon to be a molecule of great interest. DNA binding studies pointed towards anticancer potency of the synthesized compound via reversible binding.