Computational analysis was conducted to determine the bond dissociation enthalpies (BDE) of S=O bonds in eight molecules, which were subsequently compared to their experimentally derived BDEs. Computational BDE calculations were conducted utilizing various combinations of density functional theory (DFT) and basis sets. Specifically, DFT methods including M06-2X, mPW1LYP, ωB97X-D3, PBE0, and B3P86 were paired with basis sets def2-TZVP/J, def2-TZVP, aug-cc-pV(T+d)Z, 6-311++G(2df,2p), and def2-QZVP. The comparison between computational and experimental BDEs was evaluated through graphical representation, yielding slope, coefficient of determination (R2), and root mean square error (RMSE) metrics. Among the methods tested, the B3P86/aug-cc-pV(T+d)Z method performed best in terms of assessed metrics. Additionally, comparative analyses were expanded to include complete basis sets methods (CBS-QB3 and CBS-4m), which, exhibited comparatively lower accuracy in predicting experimentally calculated S=O BDEs compared to the combination methods.