Synthesis, Crystal Structure, DFT Study of m-Methoxy-N′-(3-Methoxybenzoyl)-N-Phenylbenzohydrazide

Abstract

The crystal structure of m-methoxy-N′-(m-anisoyl)-N-phenylbenzohydrazide has been determined by means of single-crystal X-ray diffraction. The title compound crystallizes in the monoclinic space group P 21/c with unit cell parameters: a = 8.7338(1), b = 24.5602(3), c = 9.6929(1) Å, β = 113.186(2)°, V = 1911.23(4) Å3, Z = 4. The dihedral angles between the mean plane of the central benzene ring and two terminal aromatic rings are 72.44(4)° and 89.90(4)°, respectively. The two methoxyphenyl rings are orthogonal with a dihedral angle of 89.74(4)°. The crystal packing is stabilized by a combination of N–H…O intermolecular hydrogen bonding and weak intermolecular C–H…O interactions. The X-ray structure was compared with the optimized counterpart calculated by the B3LYP/6-311G basis set and the results showed that the optimized geometry can reproduce the crystal structure parameters well.

A detailed computational investigation on the structural and spectroscopic properties of propolisbenzofuran B

“…These deflections are due to the fact that calculations are dependent to the gaseous phase and the experimental results are dependent to the solid phase. The crystal field in the solid state as well as the intermolecular interactions has interlocked the molecules together and therefore, the results in bond and dihedral angles may differ between the experimental and calculated values[74,75].…”

Melamine–isatin tris Schiff base as an efficient corrosion inhibitor for mild steel in 0.5 molar hydrochloric acid solution: weight loss, electrochemical and surface studies

“…Hence, strong metal–inhibitor binding and good protective ability are related with high values of E HOMO and low values of E LUMO , respectively. 43–47 The highest occupied-molecular-orbital ( E HOMO ) energy shows the capability of the tested inhibitor to donate electrons. The capability of the molecules to accept electrons from the back donation of iron, and to thus enhance the binding energy between the metal and the inhibitor is shown by a lower E LUMO value.…”

“…Fig. 8 depicts the frontier molecular orbitals (optimized, HOMO, LUMO and MEP) of MISB, while Table 5 lists the [43][44][45][46][47] The highest occupied-molecular-orbital (E HOMO ) energy shows the capability of the tested inhibitor to donate electrons. The capability of the molecules to accept electrons from the back donation of iron, and to thus enhance the binding energy between the metal and the inhibitor is shown by a lower E LUMO value.…”