Octanamides and thioctanamides containing oxygen or sulfur were synthesized and compared for score, corrosion, and wear resistance in M-11 lubricating oil against additives consisting of N,N-dibutylformamide and N,N-dibutylthioformamide. Structures were determined by IR and PMR spectroscopy and purity by gasliquid chromatography. Substituent effects are discussed. The introduction of a long alkyl chain into the thioamide improved its score and wear resistance.