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

Gordana ĆirićMarjanović | Zendy; Budimir Marjanović | Zendy; Vojislav R. Stamenković | Zendy; Željko Vitnik | Zendy; Vesna Antić | Zendy; Ivan O. Juranić | Zendy

Open Access

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

Author(s) -

Gordana ĆirićMarjanović,

Budimir Marjanović,

Vojislav R. Stamenković,

Željko Vitnik,

Vesna Antić,

Ivan O. Juranić

Publication year - 2002

Publication title -

journal of the serbian chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.227

H-Index - 45

eISSN - 1820-7421

pISSN - 0352-5139

DOI - 10.2298/jsc0212867c

Subject(s) - naphthylamine , acetonitrile , chemistry , nitrile , polymer , planarity testing , polymer chemistry , crystallography , organic chemistry

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.

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