Structure of anisole derivatives by total neutron and X-ray scattering: Evidences of weak C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions in the liquid state

High resolution, total neutron and X-ray scattering data have been used in synergy with Molecular Dynamics simulations to access atomistic scale insight into the structure of anisole and 2,3,5-trimethylanisole, two aromatic compounds bearing an electron-donating methoxy group. A detailed description is provided for the main interactions occurring in these systems, including pi center dot center dot center dot pi stacking and weak hydrogen bonding correlations: C-H center dot center dot center dot O and C-H center dot center dot center dot pi. The existence of preferential orientations of the first shell coordinating molecules and the specific nature of the interactions involving the IT cloud and the polar methoxy group have been reported and discussed. (C) 2020 Elsevier B.V. All rights reserved.