Natural bond orbital analysis, salvation, and substituent effects of electron-releasing (–CH3, –OH) and electron-withdrawing (–Cl, –NO2, –CF3) groups at para positions on the molecular structure of synthesized 3-phenylbenzo[ d]thiazole-2(3 H)-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.

We have developed herein a new approach to the diverse synthesis of novel derivatives of 3-aryl benzo[d]thiazole-2(3H)-imines (3a−g), by a two-component reaction between diazonium salt (2) and various synthesized N-acyl-N'-aryl thioureas (1a−g), in the presence of sodium tert-butoxide as strong base. Finally, it resulted in the production of the desired products with a moderate yield. The chemical structures of these synthesized compounds were confirmed by various physico-chemical methods viz. FT-IR, 1 H-NMR, 13 C-NMR, and elemental analysis.

Supporting InformationTable S1. Rotational moments of inertia and vibrational frequencies calculated at the M06-2x/aug-cc-pVTZ theoretical level for tautomeric reaction. Tautomer 1 Tautomer 2 TS Frequencies (cm 1 )

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