Substitution Effect in NICS Values in Tropylium Ion Derivatives: An Ab Initio Study

Hartree–Fock (HF) and hybrid density functional theory (B3LYP) calculations were performed on tropylium ion and 19 of its mono- and diheteroatomic derivatives. The aromaticity in this class of compounds is evaluated based on the nucleus independent chemical shift (NICS) values. The NICS values are calculated at the center of the rings NICS (0) and at 1A above the molecular plane NICS (1). The geometry optimization and NICS calculations were carried out at the HF/6–311+G∗∗ and at the B3LYP/6–311+G (2d, p) density functional level, respectively. These calculations in the effects of heteroatoms such as N, B, P, and Si are considered on aromaticity, molecular properties, NICS values, and structural parameters.