1,3-dipole

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From top to bottom,
azides, nitrones, and
nitro compounds are
examples of 1,3-dipoles.

In

1,3-dipolar cycloadditions.[1][2]

The dipole has at least one

resonance structure with positive and negative charges having a 1,3 relationship which can generally be denoted as +a−b−c, where a may be a carbon, oxygen or nitrogen, b may be nitrogen or oxygen, and c may be a carbon, oxygen or nitrogen.[3]

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

Known 1,3-dipoles are:

Carbonyl oxide

References