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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...
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Stabilizing and Activating Nitrogen Catenates.

D Scott Bohle1, Zhijie Chua2, Maya Singer Hobbs2

  • 1Department of Chemistry, McGill University, 801 Sherbrooke St. W., Montreal, H3 A 0B8 (Canada). scott.bohle@mcgill.ca.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 11, 2015
PubMed
Summary

Researchers characterized a stable hexa-nitrogen chain in bis(benzotriazene-4-one), revealing its potential for synthesizing new heterocyclic compounds. This study highlights the durability of nitrogen-nitrogen bonds in polyaza species.

Keywords:
Dimroth rearrangementazo compoundscatenationnitrogenring opening

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Area of Science:

  • Synthetic organic chemistry
  • Materials science
  • Computational chemistry

Background:

  • Nitrogen-rich compounds are of interest for energetic materials and synthesis.
  • Stable catenated nitrogen chains are challenging to synthesize and characterize.
  • Bis(benzotriazene-4-one) features a unique hexa-nitrogen chain.

Purpose of the Study:

  • To structurally, theoretically, and spectroscopically characterize the stable hexa-nitrogen chain in bis(benzotriazene-4-one).
  • To explore the reactivity of this hexaazo chain for synthesizing novel condensed heterocycles.
  • To investigate stabilization principles for polyaza species.

Main Methods:

  • Single-crystal X-ray diffraction for structural determination.
  • Density functional theory (DFT) calculations for electronic structure and bonding analysis.
  • Spectroscopic techniques (e.g., NMR, IR) for characterization.
  • Chemical reactions to probe the reactivity of the hexa-nitrogen chain.

Main Results:

  • The central N-N bond in the hexaazo chain exhibits remarkable stability.
  • Bis(benzotriazene-4-one) serves as a versatile precursor for bispyrazolones via thermal nitrogen extrusion or Dimroth intermediate trapping.
  • Trapping of a zwitterionic diazonium intermediate and generation of chelating σ-aryls using transition metals were demonstrated.
  • Stabilization is achieved through sp(2)-sp(2) N-N σ bonds with orthogonal orientations.

Conclusions:

  • The characterized hexa-nitrogen chain in bis(benzotriazene-4-one) is a stable and reactive synthon.
  • This work expands the synthetic utility of nitrogen catenates for accessing complex heterocyclic structures.
  • The findings provide insights into stabilizing and activating polyaza species for future applications.