Synthesis, Characterization, Crystal Structure and Density Functional Investigation of Dialkyl(phenyl((۴-(phenyl diazenyl)phenyl) amino)methyl) Phosphonate

The reaction of ۴-phenylazo-phenylamine and benzaldehydes with dimethyl phosphite resulted in three new α-azoaminophosphonates in excellent yields. Molecular identification of synthesized compounds were probed using NMR, FT-IR, and elemental analysis techniques. The single crystal X-ray diffraction studies were used to determine the molecular structure of dimethyl [(۴-methoxyphenyl ((۴-phenyl diazenyl) phenyl) amino) methyl] phosphonate. The synthesized molecule was crystallized in the monoclinic space group P۲۱/c with a=۱۱.۲۱۳(۲), b=۱۹.۲۰۵(۴), c=۱۱.۴۲۹(۲) Å, β = ۱۱۶.۹۵(۳), V= ۲۱۹۳.۸(۸) Å۳. Density functional theory calculation with B۳LYP/۶-۳۱۱++G (۲d, ۲p) basis set has been used to determine geometry parameters and harmonic vibrational frequencies. The optimized geometrical parameters calculated by density functional theory show satisfactory agreement with experimental values.

Keywords:

α-Azoaminophosphonates , ۴-phenylazo-phenylmine , Dimethylphosphite , single crystal , density functional theory