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Resonance structures have no real existence. These are the only theoretical
based. Also, it does not actual molecule exists as a one form for a certain fraction
of time or in another form. The resonating structures are the only an easiest way
of picturing a molecule to account for its properties.
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Out of these three structures, 3 one is ruled out because +ve charge is on
more electronegative atom.
5) The like charges should not reside on the adjacent atoms in contributing
structures.
Characteristics of Resonance:
For example, take the resonating forms of CO32- ion. For calculating C-O bond
order, consider bonds of C atom with particular O atom in all the resulting
structures.
There are 2 in structure (a),1 in structure (b)and 1 in structure (c)
While studying the concept of resonance we should be very careful about the
following misconceptions
• The sign (↔) present among the resonating structures does not
represent any kind of equilibrium.
• The real molecule cannot be depicted by single Lewis structure.
• The resonating structures (cannonical forms) have no real existence.
• The actual molecule can not be assumed to exist in one cannonical
form at one time and in other cannonical forms at other times.
1) Sulfur dioxide
Let’s consider the sulfur dioxide, SO2, molecule. Structural studies explain that
both the bonds in SO2 are of equal length and strength. This electronic
distribution is unexplained by either single Lewis structure, but is clearly
illustrated when both Lewis formulae are taken into consideration.
In resonance hybrid structure, pi electron pair is delocalized or spread
over both S-O bonds and not localized in a single S-O bond.
2) Nitrate ion
Bond length of a double bond is always shorter than single bond because the
distance between the nuclei of two atoms in a bond is less than the single bond.
But, experimentally it is found that all the 3 bonds in nitrate ion are of same
strength and same length.
It has been observed that these bonds are longer than double bond but shorter
than single bond. These are also stronger than single bonds but not as strong as
double bonds. This can be explained for the nitrate ion and polyatomic ions like it
with the help of valence-bond model.
Resonating Structure of Nitrate ion:
The actual geometry of the nitrate ion is trigonal planar with bond angles of 120º
3) Formate ion
Second resonance structure can be made from the first by shifting one
lone pair of electron down to form another bond and transferring an
adjacent bond up to form a lone pair. The arrows show the hypothetical
shift of electrons. These resonance structures lead to the resonance
hybrid as drawn below.
Exceptions:
So fluoroethene does not show resonance and only the first structure is
best described for CH2CHF molecule.
b) Taking the case of formic acid, HCO2H, which has a double bond and
an adjacent atom with a lone pair of electrons? By appearance it gives an
impression of forming a resonance structures.
Similar is the situation with oxygen atoms present in formic acid. Although
it is possible for oxygen atoms to have three bonds and one lone pair yet
it’s not possible for the oxygen atom which is the second most
electronegative element to lose the electron to form the resonance
structure of formic acid.
Thus, we will do away with resonance structures that have three bonds
and a lone pair for an oxygen atom.
The first Lewis structure is reasonable while the second one having three
bonds and a lone pair on an oxygen atom is not a reasonable resonance
structure. So formic acid does not show resonance and only the first
structure is best described for formic acid.
(1) the actual electron distribution is different than would be expected based on a
single Lewis structure, and
(2) the energy of the actual molecule is lower than expected from a single Lewis
structure. This energy lowering is due to electron delocalization and is called
resonance stabilization. The degree of energy lowering or molecular stabilization
is related to the number of resonance structures and the relative stabilities of the
resonance structures.
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