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Structure and spectroscopic characteristics of N, N'-bis(2-hydroxy-3-methoxyphenylmethylidene)-2, 6-pyridinediamine,

The Schiff base N, N¢ -bis(2-hydroxy-3-methoxyphenylmethylidene)-2, 6-pyridinediamine has been synthesized and characterized in the solid state and in solution using X-ray analysis, IR, UV/Vis and NMR spectroscopy. Crystal data: C21H19N3O4, Mr = 377.39, orthorhombic, space group Pnc2, a = 4.9288(8), b = 8.8873(19), c = 20.870(5) Å , V = 914.19(20) Å 3, Z = 2, R = 0.0387, Rw = 0.0530 for 778 independent reflections with I > 2s(I). There are two intramolecular hydrogen bonds O-H˙˙˙N between the hydroxyl and imino groups of 2.622(3) Å . The enolimino form is found in the solid state and is also the predominant tautomeric form in solution. Comparison of the title compound with the structurally related N, N¢ -bis(salicylidene)-2, 6-pyridinediamine and N, N¢ -bis(salicylidene)-2, 3-pyridinediamine is given.

N; N¢ -bis(2-hydroxy-3-methoxyphenylmethylidene)-2; 6-pyridinediamine; X-ray crystallography; IR spectroscopy; NMR spectroscopy; UV/Vis spectroscopy

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