The oxidative polycondensation reaction conditions of 4-[(2-mercaptophenyl) imino methyl] phenol (2-MPIMP) were studied in an aqueous acidic medium between 40 and 90 degrees C by using oxidants such as air, H2O2, and NaOCl. The structures of the synthesized monomer and polymer were confirmed by FTIR, H-1 NMR, C-13 NMR, and elemental analysis. The characterization was made by TGA-DTA, size exclusion chromatography (SEC) and solubility tests. At the optimum reaction conditions, the yield of poly-4-[(2-mercaptophenyl) imino methyl]phenol (P-2-MPIMP) was found to be 92% for NaOCl oxidant, 84% for H2O2 oxidant 54% for air oxidant. According to the SEC analysis, the number-average molecular weight (M-w), weight-average molecular weight (M-w), and polydispersity index values of P-2-MPIMP were found to be 1700 mol(-1) 1900 g mol(-1), and 1.118, using H2O2; 3100 g mol(-1), 3400 g mol(-1), and 1.097, using air; and 6750 g mol(-1), 6900 g mol(-1), and 1.022, using NaOCl, respectively. According to TG analysis, the weight losses of 2-MPIMP and P-2-MPIMP were found to be 95.93% and 76.41% at 1000 degrees C, respectively. P-2-MPIMP showed higher stability against thermal decomposition. Also, electrical conductivity of the P-2-MPIMP was measured, showing that the polymer is a typical semiconductor. The highest occupied molecular orbital, the lowest unoccupied molecular orbital, and the electrochemical energy gaps (E'(g),) of 2-MPIMP and P-2-MPIMP were found to be -6.1.3, -6.09; -2.65, -2.67; and 3.48, 3.42 eV, respectively. Kinetic Q thermodynamic parameters of these compounds investigated by MacCallum-Tanner and van Krevelen methods. The values of the apparent activation energies of thermal decomposition (E-a), the reaction order (n), pre-exponential factor (A), the entropy change (Delta S*), enthalpy change (Delta H*), and free energy change (Delta G*) were calculated from the TGA curves of compounds. (C) 2009 Wiley Periodicals, Inc. J Appl Polym Sci 112: 1234-1243, 2009