Thermochemistry of methyl and ethyl nitro, RNO2, and nitrite, RONO, organic compounds

Rubik Asatryan1, Joseph W Bozzelli, John M Simmie

  • 1Department of Chemistry and Environmental Science, New Jersey Institute of Technology, Newark, New Jersey 07102, USA.

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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...
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