Shape and interactions of the synthetic repellent DEET

Abstract

N,N-Diethyl-3-methylbenzamide (DEET) is the most widely used insect repellent, exhibiting high efficiency against a wide variety of species. In this work, a comprehensive isolated-molecule investigation of DEET was conducted using chirp-excitation Fourier transform microwave (CP-FTMW) spectroscopy within the frequency range of 7–14 GHz. Four out of the eight theoretically predicted conformers were detected and grouped in pairs based on their rotational constants and planar moments of inertia. We also studied the non-covalent interactions of DEET by characterizing the attractive and repulsive forces, which could explain the energetic ordering of the four conformers. In addition, DEET has a methyl top bound to the benzyl ring which is predicted to rotate almost freely with respect to the molecular framework.