Abstract
Three ortho-hydroxy Schiff bases (2-(methylimino-phenyl-methyl)-phenol (1), 4-methyl-2-(methylimino-phenyl-methyl)-phenol (2), 2-(benzylimino-phenyl-methyl)-phenol (3)) were synthesized in which the hydrogen atom in the C*C(H)*N group was substituted by a phenyl ring. Their crystal structures were determined. Strong O*H⋯N type intramolecular hydrogen bonds were found (d ON=2.496(2) A, d OH=1.11(3) A, d HN=1.45(4) A and d ON=2.488(2) A, d OH= 1.20(4) A, d HN=1.37(4) A in 1; d ON=2.505(2) A, d OH=1.16(3) A, d HN=1.39(3) A in 2; d ON=2.528(2) A, d OH=1.08(3) A, d HN=1.54(4) A in 3 together with a large proton delocalization, especially in 1 and 2. It was demonstrated that the strengthening of the hydrogen bond in comparison to related non substituted compounds results from the steric repulsion exerted by the phenyl ring.
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