Synthesis, Molecular Structure, Hirshfeld Surface Analysis, Spectroscopic and Computational Studies (DFT) of 6,6'-((1E,1'E)- (1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(2- (tert-butyl)-4-methylphenol)

Year 2019, Volume: 6 Issue: 2, 189 - 200, 15.06.2019

Pınar Şen , Sevgi Kansız , Necmi Dege

https://doi.org/10.18596/jotcsa.483143

Cited By: 2

Abstract

Schiff bases have been used in biological processes and as chelating agents for several
decades. This work presents the synthesis and
characterization of compound,
N,N’-Bis(3-tert-Butyl-5-methylsalicylidene)-1,2-diaminophenylene as the Schiff base derivative with the reaction of an aromatic aldehyde derivative and o-phenylenediamine. The spectroscopic properties of the compound were
examined by FT-IR, 1H NMR, 13C NMR,  MS and elemental analyses. The molecular structure of the compound was also confirmed
using X-ray single-crystal data. And also theoretical calculations were obtained
by using Density Functional Theory (DFT) methods. The structural parameters
were
calculated by using DFT/B3LYP/6-31G(d,p) basis set in ground state. Molecular
Electrostatic Potential (MEP) map and the frontier molecular orbitals (HOMO-LUMO) of the compound were created by using the optimized structures. The
results of theoretical study using the DFT method at the B3LYP/6–31G(d,p) level
are in good agreement with the experimental data. Hirshfeld surface analyses and
two dimensional fingerprint plots were used to analyse the intermolecular
interactions present in the crystal, indicating that the most important
contributions for the crystal packing are from H∙∙∙H
(71.2%), H∙∙∙C/C∙∙∙H (18.7%), C∙∙∙C (4.8%) and H∙∙∙N/N∙∙∙H
(2.7%) interactions.

Keywords

Synthesis, Crystal structure, Schiff base, theoretical calculation, DFT, HOMO-LUMO, MEP, FT-IR, NMR, Hirshfeld surface

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