The detailed electronic structure, spectroscopic features, and reactivity of dimethylanisoles

Abstract

The spectroscopic features, reactive natures, molecular docking, and electronic properties of anisole and six dimethylanisoles (DMAs) are investigated thoroughly to have insight into the effect of methyl substitution in anisole derivatives. The spectroscopic properties of studied molecules, including FT-IR, FT-Raman, and 1H and 13C NMR spectra were have been obtained by using DFT calculations at B3LYP/6–311++G(d,p) level of theory, and compared with the ones measured experimentally. Reactivity features were determined based on global descriptors, electron density mapping, and Fukui analysis to reveal the electrophilic and nucleophilic nature of them. The methyl position mainly affects the reactivity of the methoxy group and the aromatic nature of the ring. The methyl position dependency of aromaticity and π-stacking ability in DMAs have been explored through the nuclear independent chemical shielding (NICS) calculations, aromaticity indexes, and π orbital overlapping analysis. The static and dynamic polarizability and first and second hyperpolarizability have been carried out to explore the potential of the molecules in optical applications and the effect of methyl position on these characteristics. Bioactive potency and toxicity characteristics have been tested through molecular docking of the molecules to the odorant-binding protein.