Abstract
Abstract The structure and properties of 2-(3-pyridylmethyliminomethyl)phenol have been determined by X-ray crystallography, NMR, UV and IR spectroscopy and compared with the characteristics of the Schiff bases derived from salicylaldehyde and aminopyridines. Crystal data: C13H12N2O, Mr = 212.250, monoclinic, space group P21/n, a = 10.49(1) A, b = 9.002(4) A, c = 12.42(1) A, β = 109.10(4)°, V = 1109(2) A3, Z = 4, Dx = 1.271 g cm−3, Mokα (λ = 0.71073 A), μ = 0.8 cm−1, F(000) = 448, T = 297 K, R = 0.049, RW = 0.053 for 886 reflections with I 2σ(I). Bond distances and bond angles are similar to those of 2-(pyridyliminomethyl)phenols. In the title molecule the dihedral angle between the pyridine and benzene least-squares planes is 89.9(2)°. There is an intramolecular O1H … N1 hydrogen bond of 2.572(5) A. In solutions of polar solvents tautomeric interconversion of the Schiff base into the ketoamine is observed. Corresponding equilibrium constants are estimated in a variety of solvents on the basis of UV spectral data.
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