Charge transfer complexes of p-toluidine, Part 2: Complexes between p-toluidine with some pi-acceptors

The solid and solution interaction studies that were done between the electron donor p-toluidine and some p-acceptors such as tetrachloro-p-benzoquinone (p-chloranil), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) and 7,7,8,8-tetracyanoquinodimethane ( TCNQ) are discussed. The final product of the reactions has been isolated and characterized using UV-VIS, mid-infrared, H-1-NMR, mass spectra and thermal measurements (TGA). The molar absorptivities and formation constants of the resulting 1: 1 molecular complexes were determined. The reaction product, {[}(p-toluidine)(2)(TCNQ)] of p-toluidine with TCNQ ( 2: 1, respectively), undergoes a rapid Nsubstitution by TCNQ forming 7, 7-dicyano-8,8-di-ptoluidilequinodimethane and two molecules of HCN.