Synthesis and spectroscopic structural studies of the adducts formed in the reaction of aminopyridines with TCNQ

The adducts 7,7-dicyano-8,8-di-m-aminopyridilequinodimethane and 7,7-dicyano-8,8-di-p-aminopyridilequinodimethane are formed by the reaction of the electron donors 3-aminopyridine (3APY) and 4-aminopyridine (4APY), respectively, with the π-acceptor 7,7,8,8-tetracyanoquinodimethane (TCNQ). The reactions were studied using electronic, infrared and mass spectral and thermal measurements. The results indicate that the aminopyridines undergo rapid N-substitution by TCNQ forming the reaction products and HCN molecules. A general mechanism for the reactions as well as the structures of the reaction products are proposed.