Predicting conformations, structural and topological properties and reactivities of a fluorinated benzothiazol derivative with potential biological activites

MAXIMILIANO IRAMAIN; MARÍA F. LADETTO; SILVIA A. BRANDÁN

Descriptors, Structural and spectroscopic Properties of Heterocyclic derivatives of importance for the health and the enviroment

NOVA Science Publishers, Inc.

Año: 2015; p. 61 - 78

In this chapter, we have presented a theoretical study of the structural and topological properties of the (s)-1-(1,3-benzothiazol-2-yl)-2,2,2-trifluoroethanol derivative in gas and aqueous solution phases combining calculations derived of the density functional theory (DFT) and the available experimental crystal structure determined by X-ray diffraction. In aqueous solution, the solvent effects were studied considering the self consistent reaction force field (SCRF) calculations (IEFPCM) model. The study of the potential energy surface by using the hybrid B3LYP/-31G* level of theory reveals only a stable structure with higher population in gas phase in accordance with the experimental determined in solid phase, while in solution three stable structures with higher populations are expected. The Natural Population Atomic (NPA) and Merz-Kollman (MK) charges were studied in both media together with the bond orders, molecular electrostatic potentials, stabilization energy, solvation energy, and topological properties by using the natural bond orbital (NBO) ans the atoms in molecules theory (AIM) calculations. In addition, the highest occupied molecular orbitals (HOMO) and the lowest unoccupied molecular orbitals (LUMO) together with the chemical potential, electronegativity, global hardness, global softness, and global electrophilicity index descriptors were calculated for those stable structures in order to predict their behaviors, reactivities and stabilities in the two studied media.