Investigation of the structural properties of (E)-4-bromo-2-tert-butyl-6-[(2-chlorophenylimino)methyl]phenol by experimental X-ray diffraction and theoretical methods

This thesis is planned to investigate the Schiff base compound (E)-4-bromine-2-tert-butyl-6-[(2-chlorophenylimino)methyl]phenol (C17H17BrClNO) by single crystal X-ray diffraction method and quantum mechanical calculations. X-ray diffraction data of the investigated crystal were collected by Bruker D8-QUEST diffractometer in Sinop University Scientific and Technological Research Application and Research Centre (SUBITAM). With the data obtained, the crystal structure was solved, the geometrical and thermal parameters of the molecules and intermolecular interactions were determined. (C17H17BrClNO) compound was solved in the monoclinic P21/n space group and the unit cell parameters were determined as a=8.1741(7) Å, b=9.1175(8) Å, c=22.033(2) Å, α=γ=90.00º, β=94.382(3)º. When the C=N and C-O bond lengths determining the tautomerization of the compound were examined, it was determined that the molecule crystallized in the phenol imine tautomeric form. The angle value between the two benzene rings in the molecule shows that the molecule deviates from planarity. In this case, it can be said that (E)-4-bromine-2-tert-butyl-6-[(2-chlorophenylimino)methyl]phenol compound may have photochromic properties. As a result of the combination of weak intermolecular C-H∙∙∙∙∙Br and C-H∙∙∙∙∙Cl hydrogen bonds, repeating rings R21(6), R22(8), R21(6) and R22(8) are formed along the [110] direction. The structure also has one intermolecular π∙∙∙∙∙π interaction between benzene ring centers. In addition to the single crystal X-ray analysis, the theoretical calculations of the molecule were carried out with the Density Functional Theory method and the B3LYP/6-311+G(d,p) basis set within the Gaussian 03W software. When the geometrical parameters obtained as a result of the calculations were compared with the experimental results, high agreement was obtained.