Understanding how structure and reaction conditions influence both thermodynamic and kinetic factors affecting RCD of polycarbonates is critical to make informed decisions about the design and application of fully recyclable systems. Experimental kinetic evaluation of broad classes of polycarbonate systems containing a variety of pendant functional groups is highly tedious and labor intensive-hence reported systems for RCD of both polyesters and polycarbonates contain few examples, a narrow compositional design space, and few if any kinetic investigations of RCD. Consequently, we have demonstrated the utility of using DFTB methodology for accurate quantification of enthalpic barriers to RCD which is computationally feasible to perform on larger, more diverse datasets. Additionally, this approach allows simplification of the computation to single repeat unit, both avoiding the pitfalls of trying to model a full polymer chain while still capturing the overall trends on the influence of solvent on the enthalpic RCD barrierwhich track well with reported influences of solvents on thermodynamic parameters such as Tc.