Quantum chemical and X-ray diffraction studies of (E)-3-(((3,4-dimethoxybenzyl)imino)methyl)benzene-1,2-diol

Uzun S., DEMİRCİOĞLU Z., Tasdogan M., Ağar E.

JOURNAL OF MOLECULAR STRUCTURE, vol.1206, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1206
  • Publication Date: 2020
  • Doi Number: 10.1016/j.molstruc.2020.127749
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex, INSPEC
  • Keywords: Schiff bases, X-ray diffraction method, NLO, Hirshfeld surface analysis, DNA/ECT charge transfer, CRYSTAL-STRUCTURE, MOLECULAR-STRUCTURE, HIRSHFELD SURFACE, DFT, TAUTOMERISM, COMPLEXES, NMR, NLO, AIM
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

In this study, the target compound, (E)-3-(((3,4-dimethoxybenzyl)imino)methyl)benzene-1,2-diol, has been synthesized and characterized by FT-IR, UV-Vis and H-1 NMR, C-13 NMR methods. It's molecular structure has been experimentally elucidated by single crystal X-ray diffraction method. As a result of the X-ray diffraction experiment, it was found that the title molecule is in zwitterionic form. The minimum energy conformation in the gas phase of the title compound was achieved by density functional theory (DFT) method with the B3LYP hybrid functional using 6-31G(d,p) basis set. Accordingly, global (HOMO, LUMO, hardness and softness parameters) and local (MEP, FF, net charges) chemical activity descriptors were investigated. The stability of the molecule arising from hyperconjugative interactions, charge delocalization were analyzed by using natural bond orbital analysis (NBO) and nonlinear optical properties were investigated. Also, the interactions between the molecule with DNA bases such as adenine, cytosine, guanine, and thymine were investigated by using the ECT (electrophilicity-based charge transfer) method and Delta N (charge transfer) for investigating the charge transfer, electrophilic and nucleophilic nature. (C) 2020 Elsevier B.V. All rights reserved.