Theoretical investigations on the HOMO-LUMO gap and global reactivity descriptor studies, natural bond orbital, and nucleus-independent chemical shifts analyses of 3-phenylbenzo[d]thiazole-2(3H)-imine and itspara-substituted derivatives: Solvent and substituent effects

Natural bond orbital analysis, salvation, and substituent effects of electron-releasing (-CH3, -OH) and electron-withdrawing (-Cl, -NO2, -CF3) groups atparapositions on the molecular structure of synthesized 3-phenylbenzo[d]thiazole-2(3H)-imine and its derivatives in selected solvents (acetone, toluene, and ethanol) and in the gas phase by employing the polarizable continuum method model are studied using the M06-2x method and 6-311++G(d,p) basis set. The relative stability of the studied compounds is influenced by the possibility of intramolecular interactions between substituents and the electron donor-acceptor centers of the thiazole ring. Furthermore, atomic charges, electron density, chemical thermodynamics, energetic properties, dipole moments, and nucleus-independent chemical shifts of the studied compounds and their relative stability are considered. The dipole moment values and the highest occupied molecular orbital-lowest unoccupied molecular orbital energy gaps reveal different charge-transfer possibilities within the considered molecules. Finally, natural bond orbital analysis is carried out to picture the charge transfer between the localized bonds and lone pairs.

Automated summary

The study investigates the effects of electron-releasing and electron-withdrawing groups at para positions on the molecular structure of synthesized compounds in selected solvents and in the gas phase. Results show that intramolecular interactions between substituents and the electron donor-acceptor centers of the thiazole ring influence the relative stability of the compounds. Charge-transfer possibilities within the molecules are revealed through dipole moment values and energy gaps between occupied and unoccupied molecular orbitals.