We have recently reported a systematic investigation of the role of MQ resins (small silica-like nanoparticles) in the modulation of adhesion at silicone elastomer lens-nanometric thin acrylic surface anchored layer deposited on a silicon wafer through loading and unloading JKR experiments. This particular system was chosen as it allowed one to vary the MQ resin content in the elastomer, and to test its resulting effect on both the thermodynamic work of adhesion and the adhesive strength at elastomer-acrylic layer interfaces, avoiding any complication due to bulk mechanical properties of a relatively thick (in the micron range) acrylic layer. We present here a complementary investigation, aimed at understanding the role of the resins in the development of specific interactions at the interface. To do so the adhesive energy between silicone elastomers containing various amounts of MQ resins and model substrates made of self-assemble monolayers of thiol molecules with various amounts of carboxylic terminations have been measured through JKR tests. We show that the level adhesion at these interfaces results from a competition between increased interactions and decreased mobility associated with the incorporation of the resins inside the elastomer.