engleski

The Influence of Solvent on Molecular Properties of trans-N-Salicylideneaniline

The molecule of trans-N-salicylideneaniline (SAN) is a simple example of Schiff base with intramolecular hydrogen bond. Molecular properties, rotational barriers and solvent effects of two different conformers of SAN have been investigated by a high level ab initio reaction field theory. It has been shown recently by NMR measurements that solvent significantly affects geometry of SAN. Therefore, the solvation effects of five different solvents have been theoretically examined: benzene, chloroform, acetone, DMSO and water. The calculations were carried out with DFT quantum-chemical method using the B3LYP functional and the 6-31G(d) basis set. The calculations suggested that some geometrical parameters (e.g., torsional angles) vary upon the change of solvent. Moreover, a trend is observed that energy stabilization is proportional to the dielectric constant value. The results are compared with those of the isostructural molecule of trans-N-benzylideneaniline. The dependence of the geometry and polarization of the solute on properties of the solvent will be discussed.

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