Effects of Substituent and Temperature on the Electronic Properties and Thermodynamics Parameters of 1-(Benzothiazolylamino) Methyl-2-Naphthol: A Computational Study

Document Type : Research Paper

Authors

1 Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran

2 Department of Chemistry, Faculty of science, East Tehran Branch, Islamic Azad University, Tehran, IRAN.

3 Department of Chemistry, East Tehran Branch, Islamic Azad University, Tehran, Iran

4 Department of Chemistry, Karaj branch, Islamic Azad University, Karaj, Iran.

10.22036/org.chem.2021.245120.1254

Abstract

The effects of substituent and temperature on the 1- (benzothiazolylamino) methyl - 2- naphthol molecules were studied at CAM-B3LYP/6-311G (d,p) level of theory. Selected substitutions were NH2, OH, Me, F, Cl, CHO, COOH, CN and NO2. Substituent effect on the frontier orbitals energies, HOMO-LUMO gap, chemical potential, and electrophilicity were explored. Dependencies of energy changes, reactivity properties and thermodynamics parameters (G, H and S) on the Hammett's constants (p) were provided. Thermodynamics parameters values of the formation reaction were studied reaction at 100-1000 K range.
Computational investigation of the substituents and temperature influences on the formation reaction of the 1-(benzothiazolylamino) methyl-2-naphthol showed the negative E values in the studied reactions. Calculated dipole moment values reveal the presence of the EWGs induced a larger dipole moment compared with the EDGs. Higher negative values were found in the presence of EWGs compared to EDGs. Frontier orbitals were stabilized in the presence of EWGs. However, frontier orbitals were destabilized in the presence of EDGs. Thermodynamic analysis revealed that these reactions were non-spontaneous and exothermic. The G and negative H values were increased with increasing the temperature.
Optimization and vibrational analysis were done with Gaussian 09 software package. The standard 6-311G(d,p) basis set was considered for the elements, respectively. CAM-B3LYP functional was used for the optimization of the geometries of the compound . This functional is Handy and coworkers’ long range corrected version of B3LYP using the Coulomb-attenuating method The identities of the optimized structures as an energy minimum were confirmed by vibrational analysis

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