Exploration of the structure and interactions of 4-(dimethylamino)-3-methylphenyl N-methylcarbamate (Aminocarb).

Abstract

Aminocarb [4-(dimethylamino)-3-methylphenyl N-methylcarbamate, C₁₁H₁₆N₂O₂], a synthetic pesticide, was crystallized and characterized by single-crystal and powder X-ray diffraction. In the solid state, the molecules have a strong chain N-H...O hydrogen bond with a strength of -29.37 kJ mol^-1 and a short C-H...π contact that build a wave-like three-dimensional structure. The structural stability and intermolecular interaction of Aminocarb were investigated using differential scanning calorimetry (DSC) and density functional theory (DFT). The results show that the compound is chemically stable, and the two dominating interactions are electrostatic and dispersion energies. An electrostatic potential map reveals the binding sites of the molecules for reactivity. The understanding of the structural stability and interactions in Aminocarb provided in this study could be used to design new compounds with improved solubility and bioavailability. The dimethylamino group and the methyl group on the carbamate could be modified with other alkyl groups, which might reduce the Aminocarb toxicity, thereby leading to the development of safe, efficient and cost-effective compounds.