Synthesis, structural characterization, Hirshfeld surface and DFT based reactivity, UV filter and NLO studies of Schiff base analogue of 4-aminoantipyrine

A pyrazolone based novel Schiff base, 4-(4-benzyloxybenzalidene) amino-2,3-dimethyl-1-phenyl-3-pyrazolo-5-one (L) was synthesized by appropriate synthetic route. It was characterized by elemental-, SCXRD-, FT-IR-, UV/Vis-, ESI-MS-, and Thermogravimetric analyses. Density Functional Theory (DFT) calc...

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Bibliographic Details
Published in:Results in Chemistry 2020-01, Vol.2, p.100062, Article 100062
Main Authors: Nibila, T.A., Ahamed, T.K. Shameera, Soufeena, P.P., Muraleedharan, K., Periyat, Pradeepan, Aravindakshan, K.K.
Format: Article
Language:English
Subjects:
DFT
MEP
NLO
Pyrazolone
Schiff base
Single crystal
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Summary:A pyrazolone based novel Schiff base, 4-(4-benzyloxybenzalidene) amino-2,3-dimethyl-1-phenyl-3-pyrazolo-5-one (L) was synthesized by appropriate synthetic route. It was characterized by elemental-, SCXRD-, FT-IR-, UV/Vis-, ESI-MS-, and Thermogravimetric analyses. Density Functional Theory (DFT) calculations were carried out to obtain the ground state optimized geometry of the molecule using the B3LYP method and the 6-311++G(d,p) Basis set. Calculated geometrical parameters and spectroscopic information agreed well with the single crystal X-ray data. Reactivity (Fukui functions), electronic properties (HOMO-LUMO) and surface properties (MEP and Hirshfeld) were also studied to establish the nature of the electrophilic- and nucleophilic sites and the interactions within the crystal structure of the compound. UV–Vis spectral- and molecular orbital distribution analyses ensured the UV filter activity of the compound. The computed hyperpolarizability showed that the compound might be used for non-linear optical (NLO) applications in the near future. •Novel Schiff base, 4-(4-benzyloxybenzalidene) amino-2,3-dimethyl-1-phenyl-3- pyrazol-5-one (L) was synthesized and characterized by various instrumental techniques.•The optimized geometry of the compound has been at (B3LYP/6–311++G (d,p) level.•The experimental- and theoretical FT-IR spectra have been studied.•The experimental- and theoretical UV–Vis spectra have been studied.•NLO behaviour of the compound was investigated by the computed value of the first hyperpolarizability.
ISSN:2211-7156
2211-7156
DOI:10.1016/j.rechem.2020.100062