Synthesis of New Amides Based on the N-Hydroxyacetylation of P-Toluidine

In this research work, new amides including p-toluidiniumglycolate and 2-hydroxy-N-(4-methyl)phenylacetamidewere synthesized based on the N-hydroxyacetylation of p-toluidine. Their structure was proven by IR and 1H NMR spectroscopic methods. The synthesis methodology of new amides based on the N-hydroxyacetylation of p-toluidine was created, revealing that p-toluidiniumglycolate was formed in the environment without a catalyst and 2-hydroxy-N-(4- methyl)phenylacetamide was synthesized in the presence of an acetic acid catalyst in 85 % and 94 % reaction yields, respectively. These synthesized compounds' frequencies of the different bonds were theoretically computed and comprised with experimental results by DFT calculations with the B3LYP method (6-311G (d, p)), revealing that the similarity degrees between quantum and experimental results reported at around 95-97%. The energy differences between LUMO and HOMO for both studied organic molecules reported 0.2 and 0.148 eV respectively, confirming that both molecules are lower stability and higher reactivity