Structure and hydrogen bonding in ortho-hydroxy Ketimines

Two ortho-hydroxy Ketimines (2,2'-dihydroxybenzophenone-N-methyl-imine (1) and 2,2'-dihydroxy-4-methoxy-benzophenone-N-methyl-imine (2)) were synthesized with the hydrogen atom replaced in the azomethine group by the ortho-hydroxyphenyl substituent. The crystal structures were determined, which contain two types of hydrogen bonds; the intra-molecular (ON)-N-... (d(ON) = 2.540 Angstrom, d(ON) = 2.502 Angstrom for compound 1, d(ON) = 2.559 Angstrom for compound 2, and intermolecular (OO)-O-... (d(OO) = 2.632 Angstrom, d(OO) = 2.582 Angstrom for compound 1 and d(OO) = 2.581 Angstrom for compound 2. Fr-IR spectra of compounds 1 and 2 in solid state as function of temperature were recorded. Relation between the intra-molecular and intermolecular hydrogen bonds was discussed. Influence of methoxy group substituted in phenol ring on the hydrogen bond proper-ties has been investigated. (C) 2002 Elsevier Science B.V. All rights reserved.