Tautomeric stability, vibrational, electronic, NBO, and NMR analyses of N-[acetylamino-(3-nitrophenyl)methyl]-acetamide (ANPMA) by ab initio HF and DFT calculations

This study represents an integrated approach towards understanding the vibrational, electronic, NMR, reactivity and structural aspects of N-[acetylamino-(3-nitrophenyl)methyl]-acetamide (ANPMA). Theoretical calculations were performed by ab initio HF and density functional theory (DFT)/B3LYP method using 6-311++G(d,p) basis sets. Tautomerism and the effect of solvent on the tautomeric equilibria in the gas phase and in different solvents were studied. Electronic transitions were also studied and the most prominent transition corresponds to π → π*. ANPMA exhibited good nonlinear optical activity and 10 times greater than that of urea. Molecular electrostatic potential (MEP) results predicted that the amide group of ANPMA to be the most reactive site for both electrophilic and nucleophilic attack.

► The vibrational, electronic, NMR, and structural aspects of (ANPMA) was studied. ►Tautomerism and the effect of solvent on the tautomeric equilibria was analyzed. ► ANPMA exhibited good NLO activity. ► The amide groups of ANPMA would be the most reactive site.