The adsorption of 2-mercaptobenzoxazole on gold colloidal nanoparticles has been studied by means of Surface Enhanced Raman Scattering (SERS). SERS data have been interpreted with the help of DFT calculations on models of the ligand bound to gold adclusters. It was found that 2-mercaptobenzoxazole was adsorbed on the Au surface as thiolate through the sulphur and nitrogen atoms. The molecular plane assumes a tilted orientation with respect to the gold surface. (C) 2008 Elsevier B.V. All rights reserved.