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

Abstract

The Schiff base compound (Z)-1-((4-phenylamino)phenylamino)methylene)naphthalen-2(1H)-one has been synthesized and characterized by IR, UV-Vis, and X-ray single-crystal determination. Molecular geometry from X-ray experiment of the title compound in the ground state have been compared using the Hartree-Fock (HF) and density functional method (B3LYP) with 6-31G(d,p) basis set. Calculated results show that density functional theory DFT and HF can well reproduce the structure of the title compound. Using the time-dependent density functional theory (TD-DFT) and Hartree-Fock (TD-HF) methods, electronic absorption spectra of the title compound have been predicted and a good agreement with the TD-DFT method and experimental ones is determined. The energetic behavior of the title compound in solvent media has been examined using B3LYP method with the 6-31G(d,p) basis set by applying the polarizable continuum model (PCM). The total energy of the title compound decreases with increasing polarity of the solvent. In addition, DFT calculations of the title compound, molecular electrostatic potential (MEP), natural bond orbital analysis (NBO), and non-linear optical (NLO) properties were performed at B3LYP/6-31G(d,p) level of theory.

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

“…In general, o-hydroxy Schiff bases display two possible tautomeric forms, the enol-imine (OH) and the keto-amine (NH) forms (see Figure 1). Depending on the tautomers, two types of intramolecular hydrogen bonds are observed in Schiff bases: O-H···N in enol-imine [19,20] and N-H···O in keto-amine [21][22][23] tautomers. Different methods were used to show the presence of the enol-imine and keto-amine forms, among them UV-Vis, IR, 1 H, 13 C * Email: hasantanak@amasya.edu.tr NMR spectroscopy and X-ray crystallography techniques [24][25][26][27].…”

Experimental, theoretical and docking studies of 2-hydroxy Schiff base type compounds derived from 2-amino-4-chlorobenzenethiol

“…However, new absorption band for the 1, 2 and 3 compounds at 431, 436 and 398 (~400) nm respectively arising from π-π* transition belongs to the keto form of o-hydroxy Schiff bases [34]. The keto form is more polar than enol form; thus easily stabilized by polar solvents as DMF.…”

1-[(4-Hydroxyanilino)methylidene]naphthalen-2(1H)-one

“…The tautomerism of Schiff bases has been studied by (Alpaslan et al, 2011;Blagus et al, 2010;Ünver et al, 2002). It demonstrated that the stabilization of the Keto-amino tautomer in the crystal depend mostly on the parent o-hydroxyl aldehyde, the type of the N-substituent, the electron withdrawing or donating of the N-substituent, their position and stereo chemistry (Blagus et al, 2010).…”