Computational investigation of the synthesized new indoline-2,3-dione and their derivatives

Authors : Abolfazl SHİROUDİ

Pages : 52-65

Doi:10.33435/tcandtc.1029382

View : 62 | Download : 9

Publication Date : 2022-06-15

Article Type : Research Paper

Abstract :Computational studies using DFT incorporating the B3LYP/6-311++Ginsert ignore into journalissuearticles values(d,p); level is used to predict the stability of the synthesized 1-insert ignore into journalissuearticles values(5-phenyl-4H-1,2,4-triazol-3-yl);indoline-2,3-dione and its para-substituted insert ignore into journalissuearticles values(X: -CH3, -F, -CN, -NO2); in different solvents insert ignore into journalissuearticles values(acetone, ethanol, and methanol); and gas phases. Energetic properties, atomic charges, dipole moments, natural bond orbital insert ignore into journalissuearticles values(NBO);, molecular electrostatic potential insert ignore into journalissuearticles values(MEP);, and frontier molecular orbital insert ignore into journalissuearticles values(FMO); analyses are studied. The gauge independent atomic orbital insert ignore into journalissuearticles values(GIAO); method is used to quantify the nuclear magnetic resonance insert ignore into journalissuearticles values(NMR); chemical shift of the molecules. NBO analysis was used to assess the stability of the considered molecules, as well as their hyperconjugative relationships and electron delocalization. The charge transfer within the molecules is determined using the HOMO and LUMO analyses. The MEP surface was performed by the DFT method to predict the reactive sites for nucleophilic and electrophilic attacks. FMO analysis revealed that compound 5 insert ignore into journalissuearticles values(X=NO2); has a lower HOMO-LUMO energy insert ignore into journalissuearticles values(EHL); gaps in the considered phases, and is thus kinetically more stable in different media. Chemical reactivity indices as NO2 > CN > Cl > H > CH3 that predict the lowest insert ignore into journalissuearticles values(X=CH3); and highest insert ignore into journalissuearticles values(X=NO2); activity for the studied compounds. The energy difference derived from EHL gap leads to intramolecular hyperconjugative interactions pi→pi*.
Keywords : HOMO LUMO gap, DFT, PCM, NBO, substituent solvent effects, 1, 2, 4 triazole