Isolation and Characterization of Products from the Reaction of Organic Carcinogens with Hexavalent Chromium

We hypothesize that the coexposure of several classes of organic carcinogens with hexavalent chromium will produce electrophilic intermediates that are capable of causing DNA damage. Selected organic carcinogens were reacted with potassium dichromate in an attempt to deduce products of the reactions near biological pHs. Polycyclic aromatic hydrocarbons were shown to react only if the aromatic system was generally weak and capable of acting as a nucleophile. Polyaromatic alcohols were found to be very reactive and likely resulted in polymers that could not be isolated. Aryl amines were found to form both nitro compounds proceeding through N-hydroxy and nitroso intermediates, and azo-bonds depending upon the concentration of water present in the reaction. The hydroxyl and amino groups were found to be much more reactive at higher pHs than simple aromatic hydrocarbons.