Synthesis, characterization, crystal structure and theoretical studies of new chiral Schiff base (E)-4-hydroxy[(1-phenylethyl)iminomethyl]benzyne

Abstract

New chiral Schiff-base (E)-4-hydroxy[(1-phenylethyl)iminomethyl]benzyne (1) was synthesized through the condensation of 4-hydroxybenzaldehyde and 1-phenylethylamine in methanol at ambient temperature and characterized by elemental analyses (CHN), FT-IR, and 1H NMR spectroscopy. The crystal structure of the title compound was determined from single-crystal X-ray diffraction study. The title compound crystallizes in the orthorhombic space group P212121 with unit cell parameters: a = 5.9332(2), b = 10.0198(3), c = 20.9678(6) Ǻ, V = 1246.52(7) Ǻ3, and Z = 4. The molecular geometry of the title compound has been calculated using the density functional method (B3LYP) with 6-31G basis set and compared with the experimental data. Calculated results show that density functional theory can well reproduce the structure of the title compound. In the gas phase, the two conformers (cis and trans) for the title compound were found, with the trans isomer being the most stable one.