Spectroscopic Studies and Crystal Structure of 3-[(2-morpholinoethylimino)methyl]benzene-1,2-diol

Abstract

Schiff base 3-[(2-morpholinoethylimino)methyl]benzene-1,2-diol has been synthesized from the reaction of 4-(2-aminoethyl)morpholine with 2,3-dihydroxybenzaldehyde. The title compound has been characterized by elemental analysis, IR, 1H-NMR, 13C-NMR and UV–visible techniques. The structure of the compound also has been examined crystallographically. For the compound exist as dominant form of enol-imines in both the solutions and solid state. 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/n with a = 12.085(1), b = 8.256(1), c = 13.650(1) A, β = 108.56(1)°, V = 1291.1(2) A3, D x = 1.288 g cm−3, respectively (R 1 = 0.0336 and wR 2 = 0.0922 for 2117 reflections [I > 2σ(I)]. Intramolecular hydrogen bonding is important on the tautomeric properties and the type of aldehyde plays a vital role of the enol-imine and keto-amine properties of the Schiff base ligand.