Polarity, polarizability and molecular structure of autocomplexes on the basis of 1,4-naphthoquinone

Experimental and theoretical investigation of molecular dipole moments and molar Kerr constants of 1,4-naphthoquinone based autocomplexes has been car ried out. The results indicate the presence of intramolecular charge transf er of the n-pi* type. A correlation of the experimental values of molar Ker r constants with the sigma (0)-constants of substituents to the arylamine f ragment of the autocomplexes has been established. Substituents to the elec tron donor fragment of the autocomplexes systematically affect the angle be tween the donor and acceptor fragments. Ab initio quantum-chemical calculat ions support the n-pi*-charge transfer structure and show notable changes i n the charge on the nitrogen atom of the donor fragment due to complex form ation.