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1,3-dipole

Dipolar compound with electron delocalization and charge separation over 3 atoms

1,3-dipole

Dipolar compound with electron delocalization and charge separation over 3 atoms

In organic chemistry, a 1,3-dipolar compound or 1,3-dipole is a dipolar compound with delocalized electrons and a separation of charge over three atoms, as follows: the dipole has at least one resonance structure with positive and negative charges having a 1,3 relationship which can generally be denoted as , where a may be a carbon, oxygen or nitrogen, b may be nitrogen or oxygen, and c may be a carbon, oxygen or nitrogen.

A demonstration that how some well known 1,3-dipoles like ozone, nitro compounds and azides can be shown to have a resonance structure having 1,3 relationship between positive and negative formal charges

They are reactants in 1,3-dipolar cycloadditions.

Known 1,3-dipoles are:

  • Azides ()
  • Ozone ()
  • Nitro compounds ()
  • Diazo compounds ()
  • Some oxides
    • Azoxide compounds (RN(O)NR)
    • Carbonyl oxides (Criegee zwitterions)
    • Nitrile oxides ()
    • Nitrous oxide ()
    • Nitrones ()
Carbonyl oxide
  • Some imines:
    • Azomethine imine
    • Nitrilimines (, analogous to nitrile oxide)
    • Carbonyl imines
  • Some ylides
    • Azomethine ylide
    • Nitrile ylide ()
    • Carbonyl ylide
    • Thiosulfines ()

References

References

  1. Jagadamba, Singh. (2009). "Photochemistry and Pericyclic Reactions". New Academic Science.
  2. Francis A. Carey, Richard J. Sundberg. (2007). "Advanced Organic Chemistry". Springer.
  3. IUPAC Gold Book [http://goldbook.iupac.org/D01753.html dipolar compounds]
  4. https://www.organic-chemistry.org/namedreactions/ozonolysis-criegee-mechanism.shtm Ozonolysis mechanism on Organic Chemistry Portal site
  5. Li, Jie Jack: [https://doi.org/10.1007%2F3-540-30031-7_77 ''Criegee mechanism of ozonolysis''] Book: Name Reactions. 2006, 173-174, {{doi. 10.1007/3-540-30031-7_77
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organic-chemistry
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