Experimental and computational studies on zwitterionic (E)-2-(1-(2-(4-methylphenylsulfonamido)ethyliminio)ethyl) phenolate

Abstract

The Schiff base compound (E)-2-(1-(2-(4-methylphenylsulfonamido)ethyliminio)ethyl) phenolate has been synthesised and characterized by IR, UV-Vis, and X-ray single-crystal determination. Ab initio calculations have been carried out for the title compound using the density functional theory (DFT) and Hartree-Fock (HF) methods at 6-31G(d) basis set. The calculated results show that the DFT/B3LYP and HF can well reproduce the structure of the title compound. Using the TD-DFT and TD-HF methods, electronic absorption spectra of the title compound have been predicted and a good agreement with the TD-DFT method and the experimental ones is determined. Molecular orbital coefficient analyses reveal that the electronic transitions are mainly assigned to n ? p* and p ? p* electronic transitions. To investigate the tautomeric stability, optimization calculations at B3LYP/6-31G(d) level were performed for the NH and OH forms of the title compound. Calculated results reveal that the OH form is more stable than NH form. In addition, molecular electrostatic potential and NBO analysis of the title compound were performed at B3LYP/6-31G(d) level of theory.

Molecular structure, spectroscopic (FT-IR and UV-Vis) and DFT quantum-chemical studies on 2-[(2,4-Dimethylphenyl)iminomethyl]-6-methylphenol

“…From Table 4, we can conclude that the total molecular energies obtained by the IEF-PCM method decrease with the increasing polarity of the solvent, while the dipole moments and chemical hardness will increase with the increase of the polarity of the solvent. According to these results, the stability of the title compound increases in going from the gas phase to the solution phase [62].…”

Experimental and computational studies on (Z)-1-((4-phenylamino)phenylamino)-methylene)naphthalen-2(1H)-one

“…The weak bands in the range 3033-3000 cm -1 correspond to the symmetric and asymmetric stretching vibrations of aromatic CH bonds. The characteristic region of 1500-1700 cm -1 can be used to identify the proton transfer of Schiff bases [48]. The title compound shows a strong band at 1620 cm -1 which is assigned to C=O stretching vibration [49].…”

Interplay of thermochemistry and Structural Chemistry, the journal (volume 21, 2010) and the discipline

“…In the experimental paper by Alpaslan et al [256], synthesis, characterization, and X-ray single crystal structure determination of (E)-2-(1-(2-(4-methylphenylsulfonamido)-ethyliminio)ethyl) phenolate is reported. The results have shown that the compound exists in the zwitterionic form, which is stabilized by the intramolecular N ?…”