Theoretical study of the effect of heteroatom on the electronic and molecular properties of isoindoline monomers

Authors : Abdelkader LADJARAFI, Hacène MEGHEZZI

Pages : 31-38

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Publication Date : 2018-06-15

Article Type : Research Paper

Abstract :Theoretical calculations were carried out in the gas phase and in solution in order to study the influence of the heteroatom on the electronic and structural properties of some isoindoline derivatives and likewise to demonstrate the effect of the solvent on the tautomeric process encountered in this type of equilibrium. The most stable structures are analyzed and the possible equilibrium displacements are studied. Results of the total energies obtained with the HF, MP2 and DFT methods show firstly, that the isoindoline forms are the most stable, and secondly, that the replacement of the NH heteroatom by an oxygen heteroatom increases the stability of the compound. Calculations in solution indicate that the electronic properties of the heterocycle are influenced by the nature of the solvent which is used. However, all tautomeric forms are more stable in DMSO than in THF. The predominance of the isoindoline form in gas phase and in solution is confirmed as experimentally observed.
Keywords : isoindoline, isoindole, heterocycle, heteroatom, solvent effect, MP2, DFT