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Transforming activity of selected polycyclic aromatic hydrocarbons and their nitro-derivatives in BALB/3T3 A31-1-1

C W Sheu1, S N Dobras, I Rodriguez

  • 1Genetic Toxicology Branch, Food and Drug Administration, Washington, DC 20204.

Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association
|July 1, 1994
PubMed

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...