Stable silicon-nitrogen bonds on surface of single crystalline silicon substrates can serve a variety of practical purposes. The main problem is that creating and controlling the formation of these bonds is done predominantly in the controlled ultra-high vacuum conditions. Here the formation of stable Si-N-based interfaces will be compared for vacuum procedures and for the wet chemistry-based methods. A number of compounds, including ammonia, amines, azides and nitro-and nitroso-compounds, dosed onto a clean silicon surface can yield stable Si-N bonds. However, designing surface reactions leading to contaminant-free interfaces that contain these bonds by wet chemistry methods has been a challenge. We will use multiple spectroscopy and microscopy techniques supplemented by density functional theory investigations to build interfacial systems based on Si-N bonds with ammonia and amines reacting with Cl-covered single crystalline silicon surfaces in a solvent at room temperature. Further transformations of the produced functionalized surfaces will also be discussed.