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Charge‐Transfer Complex of p ‐Aminodiphenylamine with Maleic Anhydride: Spectroscopic, Electrochemical, and Physical Properties
Author(s) -
Karaca Erhan,
Kaplan Can Hatice,
Bozkaya Uğur,
Özçiçek Pekmez Nuran
Publication year - 2016
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201600161
Subject(s) - maleic anhydride , charge transfer complex , chemistry , cyclic voltammetry , equilibrium constant , electron acceptor , amide , molecule , thermogravimetric analysis , stability constants of complexes , gibbs free energy , polymer chemistry , organic chemistry , electrochemistry , aqueous solution , thermodynamics , electrode , copolymer , physics , polymer
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.