Forty-two peri-substituted naphthalene derivatives presenting chalcogen weak interactions were studied. They correspond to O center dot center dot center dot Y interactions, Y being O, S, and Se. While the O atom bears H or CH3 substituents (OH and OCH3 groups), the Y atom is substituted by H, F, and CN to explore the effect of these electron-donating and electron-withdrawing substituents on the chalcogen bond strength. The effect of F and CH3 substituents on positions ortho/para (2,4,5,7 of the naphthalene ring) was also studied. Optimizations were performed at the MP2/aug-cc-pVDZ, and binding energies were performed at the MP2/aug-cc-pVDZ followed by an MP2/CBS estimation. The main properties studied were geometries, energies (E-b, E-iso and E-def), the molecular electrostatic potential, electron density shifts, natural bond order E(2) energies, and the relationship between these properties.