Surface enhanced Raman scattering (SERS) is a surface-sensitive technique that utilizes metallic nanoparticles to improve the detectability of molecules down to trace levels. SERS, however, requires that molecules are close (~2 nm) to the metal, and molecular features are sensitive to intermolecular interactions. My thesis focuses on overcoming these challenges for small molecules. Specifically, small changes in vibrational spectral features are identified and subsequently attributed to dependencies on molecular structure, surface orientation, and metal affinity.