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Scanning tunneling microscopy has been used to investigate the nucleophilic substitution reaction between melamine (1,3,5-triazine-2,4,6-triamine) and terephthalaldehyde on Au/mica following deposition from solution in ambient conditions. The reaction is observed to proceed at room temperature over a time scale of days with the formation of imine oligomers intermixed with melamine islands on the Au surface. The oligomers ultimately self-assemble into a porous arrangement. The mechanism and extent of the surface confined reactions are discussed.