We have synthesized a series of monolayer-protected gold clusters (gold MPCs) featuring amide functionality within the monolayer chains. Spectroscopic investigation of these MPCs using IR and H-1 NMR spectroscopy reveal that intramonolayer hydrogen bonding is highly dependent on the distance of the amide from the nanoparticle core. Additionally, intermonolayer hydrogen bonding with concomitant nanoparticle aggregation was observed when the amide functionality was placed near the monolayer surface.