Electronic structure and aromaticity of [12]infinitene: A DFT study

Abstract

The electronic structure and aromaticity of the [12]infinitene molecule (1) and its formation via the Mallory reaction were studied using density functional theory (DFT). The examined reaction is based on a stepwise cyclization process. The nucleus-independent chemical shifts (NICS) were used to assess the aromatic character of the chemical species involved in the examined reactions. In addition, NICS-Scan, 2D and 3D multidimensional off-nucleus siso(r) magnetic shielding scans were also employed to examine the aromaticity of 1. It was found that the formation of 1 is an endothermal process, as a result of the opposed stabilizing effects of aromaticity and destabilizing effects of planarity distortions found in molecules included in the considered reaction.