Surface-enhanced Raman spectrum of anthranil (2,1-benzisoxazole) in activated silver colloid was recorded and compared with the conventional Raman spectrum. The experimentally observed Raman bands along with their corresponding infrared bands were assigned based on the results of density functional theory (DFT) calculations. The significant changes evidenced between the SER and normal Raman spectra combined with the theoretical data obtained for Ag-anthranil model systems demonstrated that this molecule is adsorbed on the colloidal silver particles through the lone pair electrons of the nitrogen atom. The contribution of the chemical mechanism to the SERS enhancement was proved by the behavior of the electronic absorption spectrum of the mixture of activated silver colloid and anthranil solution. The orientation of the adsorbed species with respect to the metal surface was also predicted.