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 its para-substituted derivatives: Solvent and substituent effects

Abstract

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.

Density Functional Theory Study of Intermolecular Interactions between Amylum and Cellulose

“…The stabilization energy E (2) between the electron donor and the acceptor was obtained from Eq. ( 5) [27].…”

Synthesis of distibiranes and azadistibiranes by cycloaddition reactions of distibenes with diazomethanes and azides

“…2 ). 17 In contrast, toluene solutions of azadistibiranes 1–3 and distibiranes 11–13 are slightly orange and yellow and only show weak adsorption bands at the edge of the visible spectrum (Fig. S49 and S52 † ), which are partially overlayed by the adsorption of the L(Me 2 N)Ga ligand.…”

Experimental and Computational Investigation on the Interaction of Anticancer Drug Gemcitabine with Human Plasma Protein: Effect of Copresence of Ibuprofen on the Binding

“…It can be seen from the values of ΔE given in Table 6 that there is not much difference in the values corresponding to various forms of gemcitabine, although the spatial arrangements of bonds as well as atoms within the molecule is different in each form, which is due to the flexibility of gemcitabine, due to which it fits inside the binding pocket of HSA [ 26 ]. Generally, a molecule with a small frontier orbital gap is more polarizable and has high chemical reactivity and low kinetic stability [ 61 ], whereas a larger gap leads to a greater molecular stability for further reactions [ 62 , 63 , 64 ]. The slight difference in ΔE observed in the present case might be due to the weaker interaction between HSA and gemcitabine because, in stronger interactions, a considerable increase in the ΔE was reported [ 21 ].…”