Molecular structure, HOMO, LUMO, MEP, natural bond orbital analysis of benzo and anthraquinodimethane derivatives

Tahar Abbaz, Amel Bendjeddou, Didier Villemin


Objective: Optimized molecular structures have been investigated by DFT/B3LYP method with 6-31G (d,p) basis set. Stability of Benzo and anthraquinodimethane derivatives 1-4, hyperconjugative interactions, charge delocalization and intramolecular hydrogen bond has been analyzed by using natural bond orbital (NBO) analysis. Electronic structures were discussed and the relocation of the electron density was determined. Molecular electrostatic potential (MEP), local density functional descriptors has been studied. Nonlinear optical (NLO) properties were also investigated. In addition, frontier molecular orbitals analyses have been performed from the optimized geometries. An ionization potential (I), electron affinity (A), electrophilicity index (ω), chemical potential (µ), electronegativity (χ), hardness (η), and softness (S), have been investigated. All the above calculations are made by the method mentioned above.

Methods: The most stable optimized geometries obtained from DFT/B3LYP method with 6-31G(d,p) basis set were investigated for the study of molecular structures, nonlinear properties, natural bond orbital (NBO), molecular electrostatic potential (MEP) and frontier molecular orbital of Benzo and anthraquinodimethane derivatives.

Results: Reactive sites of electrophilic and nucleophilic attacks for the investigated molecule were predicted using MEP at the B3LYP/6-31G(d,p). Compound 4 possesses higher electronegativity value than all compounds so; it is the best electron acceptor; the more reactive sites for electrophilic attacks are shown in compounds 1 and 4, for nucleophilic attacks are indicated in compounds 2 and 3 and the more reactive sites in radical attacks are detected in compounds 2 and 4.

Conclusions: Compound 1 is softest, best electron donor and more reactive than all compounds. The calculated first order hyperpolarizability was found much lesser than reported in literature for urea.


Tetrathiafulvalenes, Density functional theory, Computational chemistry, Electronic structure, Quantum chemical calculations

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