1,3-dipole





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

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. They are reactants in 1,3-dipolar cycloadditions.

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.

Known 1,3-dipoles are:

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