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Poly-(1-naphthylamine) films were synthesized potentiodinamically and potenti- ostatically from 1-naphthylamine in neutral acetonitrile medium using a platinum electrode. These polymer films were investigated by infrared spectroscopy. Contrary to earlier pub- lished results neglecting the stereochemistry of the poly-(1-naphthylamine), we predict on the basis of quantum stereochemical analysis of the possible structural subunits of the poly- mer, that the ordinary N-C(4) coupled product is not predominant in the polymer because it is far removed from the expected planarity. Based on the results of IR investigations and semiempirical quantum chemical calculations, it is proposed that the polymer products are formed via mixed N-C(4), N-C(5) and N-C(7) coupling routes. The heats of formation of the oxidized 1-naphthylamine dimers and hexamers were calculated.

Structure and stereochemistry of electrochemically synthesized poly-(l-naphthylamine) from neutral aceto- nitrile solution