Molecular Complexes of Dichloro-p-Benzoquinone Derivatives with Aromatic Amines

Chemistry Department, Faculty of Education, King Abdulaziz University, Mecca, Saudi Arabia

Manuscript received 21 April 1979, accepted 25 December 1979

Molecular complexes of substituted anilines with chloranilic acid (I) and dichloro­dicyano-\(p\)-benzoquinone (II) are prepared and investigated by infrared spectroscopy. Anilines substituted at the aromatic ring form two types of compounds involving either a \(\pi\)-\(\pi\)* interaction or a proton transfer besides the \(\pi\)-\(\pi\)* C.T. with I while II formed the anilide. N-Substituted anilines form compounds involving \(\pi\)-\(\pi\)* C.T. or \(\pi\)-\(\pi\)* and \(\pi\)-\(\pi\)* interactions depending on the electronic character of the substituent on the N-atom.