We present a Monte Carlo approach to estimate how molecular parameters impact hopping rates and chargemobilities in organic π-conjugated materials. Our goal is to help in establishing structure−propertiesrelationships. As a first step, our approach is illustrated by considering a model system made of a one-dimensional array of pentacene molecules; we describe the variations of the electron-transfer rates and of theresulting charge mobilities as a function of electric field and of the presence of molecular disorder and traps.The results highlight that there is no direct relationship between the degree of spatial overlap among adjacentmolecules and charge mobility.