SYNTHESIS AND STRUCTURE OF THE HEMISOLVATE FORMED BY CHLOROBENZENE WITH 1-(4-DIETHYLAMINOPHENYL)-HYDRAZO-3-PHENYLAMIDO-1,2-NAPHTHOQUINONE

Article abstract of DOI:10.1007/BF00746937

Systematic research is being done on the structures of azo pigments in the 2-oxy-3-naphthoic acid arylamide series in connection with their tautomerism; in this connection, 1-(4-diethylaminophenyl)-hydrazo-3-phenylamido-1,2-naphthoquinone (Ia) has been synthesized and used in an x-ray structure study of its hemisolvate with chlorobenzene.Ia has a mainly hydrazone structure, with a considerable contribution from the azo component, which makes itself felt in substantial shortening in the intramolecular N(2)-H(2)...O(1) hydrogen bond (H...O distance 1.65(6) Angstroem) and in the distribution of the bond lengths in the hydrazoquinone part of the molecule, which is due to the strong electron-donor effect from the p-diethylamino substituent.The solvate molecules in the crystal do not have an appreciable effect on the molecular structure of Ia.