INFRARED STUDY OF THE CONFORMATION AND COMPLEXING ABILITY OF 9,10-DIAMINOPHENANTHRENE

The IR spectra of partially deuterated 9,10-diaminophenanthrene in sol ution show double intramolecular NH...N hydrogen bonds in which the tw o NHD groups are equivalent. This is in contrast with the spectroscopi c data in the solid state where, by analogy with o-phenylenediamine, t he two intramolecular hydrogen bonds seem to be slightly different. Th e formation constants for complexes involving phenols are determined i n C2Cl4. The IR data in the NH2 stretching region suggest that, in the se complexes, one of the intramolecular hydrogen bonds is broken and t he second one reinforced by cooperativity.