CRYSTAL STRUCTURE, SPECTRAL CHARACTERIZATION, MOLECULAR MODELING STUDIES AND STRUCTURAL EFFECTS OF THE PROTON TRANSFER PROCESS FOR (E)-5-METHOXY-2-[(3,4-DIMETHYLPHENYLIMINO)METHYL]PHENOL
[ X ]
Tarih
2017
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Soc Chemists Technologists Madeconia
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
The main purpose of this study is to characterize a new organic material, (E)-5-methoxy-2-[(3,4-dimethylphenylimino) methyl] phenol, which was synthesized and grown as a single crystal. The molecular structure and spectroscopic properties of the ortho-hydroxy Schiff base compound were determined by X-ray diffraction analysis, Fourier-transform infrared (FT-IR), ultraviolet-visible (UV-Vis) and nuclear magnetic resonance (NMR) spectroscopy techniques, experimentally and computationally with density functional theory (DFT) calculations. X-ray and UV-Vis studies show that the compound exists in an OH tautomeric form in the solid and solvent media. The gas phase geometry optimizations of two possible forms of the title compound, resulting from the prototropic tautomerism, were obtained using DFT calculations at the B3LYP/6-311G+(d,p) level of theory. A relaxed potential energy surface (PES) scan was performed based on the optimized geometry of the OH tautomeric form by varying the redundant internal coordinate, the O-H bond distance. According to the PES scan process, the molecular geometry is strongly affected by the intramolecular proton transfer. The calculated first hyperpolarizability indicates that the compound could be a good material for non-linear optical applications.
Açıklama
Anahtar Kelimeler
Schiff base, prototropic tautomerism, intramolecular proton transfer, NLO, DFT
Kaynak
Macedonian Journal of Chemistry and Chemical Engineering
WoS Q Değeri
Q3
Scopus Q Değeri
Q3
Cilt
36
Sayı
2
