Molecular orbital, spectroscopic, first order hyperpolarizability and NBO analysis of aryl-substituted 5-(benzylidine) thiazolidine-2,4-diones

Fatma, Shaheen ; Parveen, Huda ; Bishnoi, Abha ; Verma, Anil Kumar; Srivastava, Krishna


In this study, the structure of three 5-(4-subs/3, 4- di substituted benzylidene) thiazolidine-2,4-diones has been studied by using density functional theory (DFT) at 6-31G(d,p) level basis set. Detailed interpretations of the vibrational spectra of these compounds have been made on the basis of the calculated potential energy distribution (PED). The 1H and 13C NMR spectra have been recorded and the chemical shifts have been calculated using the gauge- independent atomic orbital method (GIAO). The values of frontier orbital energy gap (-3.64 eV) and dipole moment (4.7012 D) show that the compound 3b is less reactive and less polar, hence the most stable among the three molecules. The significantly higher value (131.96×10-30 esu) of total hyperpolarizability for compound 3c indicates the better use of this molecule as NLO material. The calculated local reactivity descriptors for 3(a-c) indicate that C2 is the most reactive site for nucleophilic attack whereas the oxygen attached to this C is more prone to electrophilic attack. Hyperconjugative interactions have been studied with the help of natural bond orbital analysis. The electronic properties and thermodynamic properties have also been performed.


Density functional theory (DFT); Natural Bond Orbital (NBO); Non linear optical (NLO); Molecular electrostatic potential (MESP); Hyperpolarizability

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