Although addition of geminal di-substitution or fused/bridged/spiro rings are effective for lactones and lactams to improve depolymerizability, these impact of these features in 6-membered cyclic carbonates on the polymerization process, the ∆Hp and ∆Sp of the monomer, and the kinetics of depolymerization under different conditions are poorly understood. Finally, while ∆Hp and ∆Sp are useful in assessing the thermodynamic potential for depolymerization, it is experimentally unfeasible to measure them across all monomer types and reaction conditions and moreover, these values do not provide information on the energy barrier to RCD (Fig. ). Thus, there exists a need for computational methodology to provide insight into complex reactivity trends in regimes where accessing experimental data is costly and historical data is minimal. Here, we show that using empirical computational techniques such as Density-Functional Tight-Binding (DFTB), it is possible to more quickly explore monomer chemical space and build understanding around potential solvent-structure interrelationships via analysis of enthalpic barriers to depolymerization. In turn, this high-throughput barrier characterization process can be used for screening of depolymerization of polycarbonate oligomers and act as an upper bound on quantitative measurements.