The adsorption of a bi-functional organic molecule like phenol on Si(100)2 x 1 has been investigated by synchrotron radiation-induced photoemission in the valence band, Si 2p, C 1s and O 1s core-level regions. Experiments have been carried out as a function of phenol exposure at room temperature. Phenol adsorbs on Si(100)2 x 1 through a dissociative mechanism at room temperature, interacting with the surface by its alcoholic functionality. The line-shape analysis of Si 2p spectra indicates the formation of Si-O and Si-H bonds, as a consequence of the cleavage of the C6H5O-H bond and the binding of the fragments (C6H5O-group and H atom) to the Si(100)2 x 1 surface dimers. The progressive quenching of the silicon surface dimer atoms and the c...