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

Abstract

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.

Structure and surface analyses of a newly synthesized acyl thiourea derivative along with its in silico and in vitro investigations for RNR, DNA binding, urease inhibition and radical scavenging activities

“…The energy gap between LUMO and HOMO determine the electronic structure that could further lead to predict the kinetic stability and reactivity of a compound. 42 The compound (4) was detected to be unstable one because of the small energy gap (Δ E ) value; hence could be inferred as reactive in nature, Table 3 . The small value of hardness ( η ), while a greater value of softness ( S ) further indicated the polarizable nature of the compound (4), as also obvious from computed polarizability and dipole moment values and validated its instability that is necessary for its binding interactions with protein/or DNA molecule, Table 3 ,.…”

Single crystal, Hirshfeld surface, DFT analyses of (E)‐2‐(2‐chloro‐6‐fluorobenzylidene)hydrazinecarbothioamide: Elastase inhibition and DNA binding studies

“…[ 19,46 ] The spectral changes indicated that compound 3 intercalated via partial/or complete insertion into DNA base pairs. [ 17,47 ] Intercalation feasibility could be accredited to planarity in the compound's structure and related to the overlapping of intercalating chromophore's electronic state (π * antibonding orbitals) and stacked DNA base pairs (π bonding orbitals). This overlapping causes π ‐ π * coupling that decreases transition probability hence resulted in hypochromism in the compound's spectra after the addition of DNA.…”

DNA interactive and selective anticancer activity studies of copper(II) complexes decorated water‐soluble porphyrin

“…Figure 10 shows the optimized structures of cationic porphyrin ligand ([L] 3+ ) and complexes ([Cu‐P1] 3+ , [Cu‐P2] 3+ , and [Cu‐P3] 3+ ), and then, their energy gap (Δ E ) (the difference between highest occupied molecular orbital [HOMO] and lowest unoccupied molecular orbital [LUMO]) are discussed in details; it plays important roles in determining electronic structures and the analysis of chemical reactions. [ 76–78 ] The frontier molecular orbital structures and calculated HOMO–LUMO energy gap (Δ E ) of cationic porphyrin ligand and complexes are described in Figures 11 and S16. The HOMO of ligand [L] 3+ was placed on Schiff base moiety, and LUMO was on the porphyrin ring.…”

“…Figure 10 shows the optimized structures of cationic porphyrin ligand ([L] 3+ ) and complexes ([Cu-P1] 3+ , [Cu-P2] 3+ , and [Cu-P3] 3+ ), and then, their energy gap (ΔE) (the difference between highest occupied molecular orbital [HOMO] and lowest unoccupied molecular orbital [LUMO]) are discussed in details; it plays important roles in determining electronic structures and the analysis of chemical reactions. [76][77][78] The frontier molecular orbital structures and calculated HOMO-LUMO energy gap (ΔE) of cationic porphyrin ligand and complexes are described in Figures 11 and S16 surrounding of the metal center, but HOMO mainly localized at porphyrin complexes and LUMO at Schiff base complexes. Calculated HOMO-LUMO energy gap (ΔE) of complexes (0.33, 0.38, and 0.36 eV) was lower than free ligands (1.20 eV); these are attributed to after complexation of Cu 2+ , and there is a disruption of internal charge transfer that leads to changes in electronic properties.…”