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Journal of the Serbian Chemical Society 2002 Volume 67, Issue 12, Pages: 867-877
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Structure and stereochemistry of electrochemically synthesized poly-(l-naphthylamine) from neutral aceto- nitrile solution

Ćirić-Marjanović Gordana N., Marjanović Budimir, Stamenković Vojislav, Vitnik Željko J., Antić Vesna V., Juranić Ivan O.

Poly-(1-naphthylamine) films were synthesized potentiodinamically and potentiostatically from 1-naphthylamine in neutral acetonitrile medium using a platinum electrode. These polymer films were investigated by infrared spectroscopy. Contrary to earlier published 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 polymer, 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.

Keywords: coupling routes, infrared spectroscopy, polymer structure, poly-(1-naphthylamine) films, stereochemistry.