title: Charge-Transfer Complex of p-Aminodiphenylamine with Maleic Anhydride: Spectroscopic, Electrochemical, and Physical Properties.
abstract: A new charge-transfer complex and the amide formed by the interaction between the electron donor of the p-aminodiphenylamine and the electron acceptor of maleic anhydride are investigated by spectroscopic methods. The amidation reaction is caused by proton and charge transfer between the maleic anhydride and p-aminodiphenylamine molecules. The Benesi-Hildebrand equation is used to determine the formation constant, the molar extinction coefficient and the standard Gibbs free energy of the complex by using UV/Vis spectroscopy. To reveal the electronic and spectroscopic properties of these molecules, theoretical computations are performed on the structures of maleic anhydride, p-aminodiphenylamine and the conformers of their charge-transfer complex. The charge-transfer complex and amidation reaction mechanism are also confirmed by IR and NMR spectroscopy and HRMS. The nature of the maleic anhydride-p-aminodiphenylamine complex is characterized by cyclic voltammetry, thermogravimetric analysis, XRD and SEM. Solid microribbons of this complex show higher thermal stability than p-aminodiphenylamine.
authors.affiliation: Hacettepe University, Department of Chemistry, 06800, Beytepe, Ankara, Turkey.
authors.forename: Erhan
authors.initials: E
authors.lastname: Karaca
authors.affiliation: Hacettepe University, Department of Chemistry, 06800, Beytepe, Ankara, Turkey.
authors.forename: Hatice
authors.initials: H
authors.lastname: Kaplan Can
authors.affiliation: Hacettepe University, Department of Chemistry, 06800, Beytepe, Ankara, Turkey.
authors.forename: Uğur
authors.initials: U
authors.lastname: Bozkaya
authors.affiliation: Hacettepe University, Department of Chemistry, 06800, Beytepe, Ankara, Turkey. npekmez@hacettepe.edu.tr.
authors.forename: Nuran
authors.identifier: http://orcid.org/0000-0002-7223-790X
authors.initials: N
authors.lastname: Özçiçek Pekmez
keywords: NMR spectroscopy; UV/Vis spectroscopy; charge-transfer complexes; maleic anhydride; p-aminodiphenylamine