Resonance

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If a compound have more than one possible structure then these structures then
the combination of several contributing structures (or forms, also variously known as
resonance structures or canonical structures) into a resonance hybrid (or hybrid
structure) and this phenomenon is called resonance

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The "real" structure has characteristics of each of the contributors, and is often represented as the
resonance hybrid (think of a hybrid breed which is a mixed breed). In a way, the resonance
hybrid is a mixture of the contributors.

Resonance Structures of NO3– Ion he

Nitrogen is the central atom in a nitrate ion. It is singly bonded to two oxygen atoms and doubly
bonded to one oxygen atom. The oxygen atoms that are singly bonded to the nitrogen hold a charge
of -1 (in order to satisfy the octet configuration). The central nitrogen atom has a charge of +1 and
the overall charge on the nitrate ion is -1. The three possible resonance structures of NO3– are
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illustrated below.
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Resonance Structures of NO3- Ion

If a resonance hybrid of this polyatomic ion is drawn from the set of Lewis
structures provided above, the partial charge on each oxygen atom will be
equal to -(⅔). The net charge on the central atom remains +1. This
resonance hybrid is illustrated below.
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Resonance Structures of O3
The ozone (O3) molecule consists of a central oxygen atom which is singly bonded to one oxygen
atom and doubly bonded to another. There is no net charge on this molecule, but the Lewis

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structures of this molecule show a +1 charge on the central oxygen and a -1 charge on the singly

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bonded oxygen. The two resonance structures of the ozone molecule are illustrated below.

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Resonance Structures of O3

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The resonance hybrid of ozone has a +1 charge associated with the oxygen at the centre and a
partial charge of -(½) associated with the other oxygen atoms.

Rules to remember for recognising resonance structures:

 Atoms never move.

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You can only move electrons in  bonds or lone pairs (that are in p orbitals)
The overall charge of the system must remain the same.
The bonding framework of a molecule must remain intact.

Ranking resonance structures (for 1st row atoms, in order of importance):

 Octet rule should be satisfied.

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 Charge separation requires energy (think electrostatics)

Resonance energy The difference between the potential energy of the actual structure (the
resonance hybrid) and that of the contributing structure with the lowest potential energy is called the
"resonance energy".
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1. H3PO3 can be represented by structures 1 and 2 shown below. Can
these two structures be taken as the canonical forms of the resonance
hybrid representing H3PO3 ? If not, give reasons for the same.
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