Spectroscopic Studies and Crystal Structure of (Z)-6-[(2-hydroxyphenylamino)methylene]-2-methoxycyclohexa-2,4-dienone

Abstract

The Schiff base (Z)-6-[(2-hydroxyphenylamino)methylene]-2-methoxycyclohexa-2,4-dienone has been synthesized from the reaction of 2-aminophenol with 2-hydroxy-3-methoxybenzaldehyde. The title compound has been characterized by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and UV–Visible techniques. The structure of the title compound also was determined crystallographically. The crystal structure has been solved by direct methods and refined by full-matrix least squares. The title compound crystallize in the monoclinic space group P21/c with a = 10.438(1), b = 8.851(1), c = 12.746(1) A, β = 95.72(1)°, V = 1171.7(2) A3, D x = 1.379 g cm−3, respectively (R1 = 0.0522 and wR2 = 0.126 for 1442 reflections [I > 2σ(I)]). N-salicylideneaniline derivatives have been shown to exist as tautomeric forms due to intramolecular proton shifts between the phenol-oxygen and the imine-nitrogen, via intramolecular hydrogen bonding O–H···N or O···H–N.