Decarboxylation is an abundant yet unique reaction that is often unfavorable and requires a catalyst. In this work, the favorability of decarboxylation was studied through analysis of the change in Gibbs Free Energy (?G) in relation to changing substituents around a carboxylate group. To quantify the impact of substituents on the ?G of decarboxylation, natural bond order (NBO) analyses were calculated for each reaction using the NBO 7 program hosted in Gaussian 16. Statistical analysis evaluated the relationships between elements of the NBO calculation, such as bond occupancies, bond energies, and orbital information, and the ?G values for each reaction. Leading candidates from the NBO calculations have emerged as predictors for more favorable decarboxylations, providing future insight into the mechanism of decarboxylation.