Abstract
Charge-transfer (CT) complex of
o
-toluidine (
o
-tol) with the π-acceptor tetrachloro-
p
-benzoquinone (
p
-chloranil; CHL) has been synthesized and characterized, along with the products of the elimination reaction of
o
-toluidine (
o
-tol) with 2,3-dichloro-5,6-dicyano-
p
-benzoquinone (DDQ) and 7,7,8,8-tetracyanoquinodimethane (TCNQ). Their properties and structures have been investigated using electronic absorption and IR spectroscopy as well as elemental analyses of the isolated compounds. The
o
-tol/
p
-CHL CT complex is shown to consist of a CHL
−
radical anion and
o
-tol
+
radical cation. The formations of all three compounds result in the appearance of new UV-Vis spectral bands that peaked in intensity at a stoichiometric ratio of 1:1.
1
H-NMR and mass spectra were used to confirm the formation of the
o
-tol/DDQ and
o
-tol/TCNQ products. The new 7,8-dicyano-7′,8′-
o
-toluidilequino-dimethane and 2,3-dichloro-5-cyano-6-
o
-toluidil-
p
-benzoquinone products resulted from the rapid reaction of
o
-tol with TCNQ and DDQ, respectively. Thermogravimetric studies showed that the CT-complex decomposes in three steps whereas the new compounds decompose in a single step. Thermodynamic parameters were computed from the thermal decomposition data.