Tautomeric transformations and reactivity of isoindole and sila-indole: A computational study

Abstract

In this work, the tautomeric transformations and reactivity of isoindole and sila-isoindole molecules has been explored using the B3LYP/6-311G(d,p) level of theory in gas and solution phases. These calculations show that isoindole isomer has more stability rather than 1-h-isoindole. There is identical trend in silated species. The frontier molecular orbitals (FMO) and band gap energy calculations were performed at the B3LYP/6-311G(d,p) level in gas and various solvent. Solvent effects have been analyzed by using the self-consistent reaction field (SCRF) method based on polarizable continuum model (PCM) in chloroform, chlorobenzene, dichloromethane and tetrahydrofurane. Thermodynamic parameters calculated at room temperature have been analyzed. Also, electron affinities were computed. Local reactivity descriptors as Fukui functions [Formula: see text] local softness [Formula: see text] and electrophilicity indices [Formula: see text] analyses are performed to find out the reactive sites within molecule. Density functional theory (DFT) calculations were performed to compute nitrogen-14 nuclear quadrupole resonance (NQR) spectroscopy parameters.