Resonance

David Du
BIALIGY.com

December 2020

§1 Resonance
Sometimes, even after Lewis structures are drawn an formal charges are determined, there is no one
structure that can be represented. Resonance is a way to describe molecules that have more than one
structure. Let’s look at the nitrate ion NO−
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We can actually redistribute the double bond to the other oxygens and maintain the same formal charge
on each of the atoms, and since the center atom has an octet and will remain the octet even if we shift
the double bond.

Basically what this structure and the arrows are saying is that the nitrate molecule can exists as these
different structures simultaneously, meaning that the electrons on the oxygen are instantaneously shifting,
which is called electron delocalisation. Because of electron delocalisation, the bonds on the nitrogen are
not in essence a double bond nor a single bond, but rather somewhere inbetween. How much inbetween
is determined by the bond order.

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Resonance BIALIGY.COM David Du

Definition §1.0.1: Bond Order

number of bonds
Bond Order =
number of atoms

In the nitrate ion, there are 4 bonds shared between the nitrogen and the oxygen, with 3 oxygen
atoms. So the bond order is 4/3 = 1.3. Usually, double bonds have a bond order of 2 while single bonds
have a bond order of 1. So we can see that is the bonds are somewhere inbetween a single and double
bond. We write this structure using dotted lines as