The carbon-nitrogen bond in formamide, HCONH2, has been shown to have a bond length that is in between a typical C-N single bond
1 answer:
The true structure of HCONH2 is a resonance hybrid of two structures.
Linus Pauling introduced the idea of resonance to explain the observed properties and bond lengths of some compounds.
Resonance occurs where there is a movement of electrons within a molecule. This electron redistribution affects properties of the molecule such as bond lengths and bond distances.
Since the lone pair on the nitrogen of the amine group participates in resonance with the carbonyl moiety in the molecule, a resonance is set up as shown in the image attached to this answer.
This resonance accounts for the fact that the HCONH2 has been shown to have a bond length that is in between a typical C-N single bond and a C=N double bond.
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