Chemical Bonding

Petrucci, Herring Madura and Bissonnette :

Chapters 10 and 11
Aims:
To look at bonding and possible shapes of molecules
We will mainly do this through Lewis structures

To look at ionic and covalent bonds

Use valence shell electronic structure to predict shapes of
molecules

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Chemical Bonding 1

Problem set
Chapter 10 questions 3, 4, 11, 17, 18, 21,
22b), 59, 62, 141
Chapter 11 questions 7, 13, 17

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Chemical Bonding 2

Chemical Bonding
Lewis Theory:
Electrons, particularly valence electrons play a
fundamental role in chemical bonding.
When elements combine to produce compounds
they are attempting to achieve a full valence
shell (usually 8 electrons) aka octets

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Chemical Bonding 3

Chemical Bonding
Lewis Theory:
Electrons can be transferred from one atom to
another to make ions. The atoms are then held
together by coulombic forces in an ionic bond
More often the only way an atom can gain
electrons is by sharing. This sharing produces a
covalent bond
between 2 non metals

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Chemical Bonding 4

Lewis Symbols
This is a way of representing the valence
electrons in an element
It does not include the inner shell electrons
It does not include the spin of an electron
e.g. Si ([Ne]3s23p2)
N ([He]2s22p3)

Si

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Lewis Structures
These are the combination of Lewis symbols that
represents the sharing or transfer of electrons in a
molecule
Ionic bonding examples ( electron transfer)

Na x

Cl

Mgxx + 2 Cl

[Na]+ [ Cl ]x

[Mg]2+ 2 [ Cl ]x

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Ionic Compounds
We dont usually see isolated ionic compounds
aka ionic crystals

Normally they are in crystals where one anion

(negative) is attached to several cations (positive)
and vice versa. Electrical neutrality means the total
number of each ion is the same.

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Ionic Compounds

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Lewis Structures
These are the combination of Lewis symbols that
represents the sharing or transfer of electrons in a
molecule
Covalent bonding example (sharing)
x

H + Cl

H Cl

not ionic because H is non metal even though its on left side

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Chemical Bonding 9

Covalent Compounds
Here electrons are shared between two atoms.
Why? Because the energy cost of making the ions is too
high IE for H is 1312 kJ/mol
Could be more than just a couple of shared electrons
The electrons are associated with each atom in the
covalent bond
The overall effect is that each atom has more (usually
a full shell of) valence electrons.

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Chemical Bonding 10

Covalent Compounds
Examples
Single covalent bond HCl

Lone pairs

Bond pair

H Cl

H Cl

Note that there are 6 electrons around the Cl that

are not involved in bonding. It is normal to talk
about these as lone pairs, in contrast to bond
pairs
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Chemical Bonding 11

Coordinate Covalent Bonds

single atom contributes both e- to a shared pair

Bonds do not have to come from equal sharing of

electrons

In NH4+ there are 8 electrons around the N, but it has 5

to start with. Hence the hydrogens only contribute 3 of
the 8 bonding electrons.
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Multiple Covalent Bonds

Often the sharing of one electron does not
fill the valence shell of an atom.
e.g. N2
N

N
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N
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Multiple Bonds
We use a number of different ways to
describe multiple bonds
For 1 bond pair
For 3 bond pair
Single bond
bond order =1

Triple bond
bond order =3

For 2 bond pairs

Double bond
bond order =2
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Bond Length
Bond Length
The distance between two atoms joined by a
covalent bond
As the bond order increases the bond length
decreases
Bond

Length/pm

Bond

Length/pm

C-C
C=C
C C

154
134
120

N-N
N=N
N N

145
123
110

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Bond Energy
To separate two atoms that are joined by a
covalent bond, energy must be supplied. This is
the Bond Dissociation Energy (D).
This is equal to the energy released when the bond
is formed.
H2(g) 2H(g)

H = D(H-H) = +435.93 kJ mol-1

Listed bond energies are usually an average over a number

of compounds

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Polarity of Bonds
In most molecules the bonding is not 100%
ionic or 100% covalent (equal sharing)
Start from the covalent side
Unequal sharing of electrons in a bond means
one atom is slightly positive (+) and the other
slightly negative (-).
This leads to a polar covalent bond.
non-metallic element has more of the electron density

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Chemical Bonding 17

Charge density (electrostatic potential)

This is a map that shows the surface that shows
where the charge is located
less e-

Ionic
<100% Covalent
100% covalent

more e-

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Polarity of Bonds
The ability to attract electrons in a bond
appears to be related to electron affinity but
we need to use a molecular property to
describe it.
Electronegativity is a quantitative measure
of an atoms ability to compete for electrons
with other atoms to which it is bonded.
Actually the difference between an atoms
ionization energy and its electron affinity
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electronegativity (EN) depends on ionization energy (IE)-electron affinity (EA)

Chemical Bonding 19

Polarity of Bonds:
Electronegativities

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Polarity of Bonds
Thus the difference in electronegativities
between atoms in a bond gives a measure of
the polarity.
This can also be interpreted as the ionic
character of a bond

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Polarity of Bonds:
Ionic Character
The larger the
electronegativity
difference between
the atoms, the more
ionic the bond.
if difference in electronegativity >1.7,
bond is ionic

1.7

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Lewis Structures
Lewis structures are useful in indicating the
bonding in molecules.
Rules:
All valence electrons must appear
The electrons are usually paired
The valence shells are usually filled (2 electrons for H,
8 for systems with s and p orbitals)
Multiple bonds are often needed, especially in C, N, O,
P, S.
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Lewis Structures
1. Check if the compound is ionic. If it is, treat
each ion separately.
2. Add up the number of valence electrons (thats
from all atoms). Add or subtract electrons to
give the right charge. This is the available
electrons A.
3. Draw a skeletal structure. The central atom will
normally have the lowest electronegativity.
Carbon is always a central atom. Hydrogen is
always terminal.

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Chemical Bonding 24

Lewis Structures
4. Calculate the number of valence electrons
needed to give all the atoms a full shell (2 or 8).
This is the number of needed electrons N
5. Determine the number of electrons that must be
shared S=N-A
6. Place single bonds in the skeletal structure (2
electrons per). Add extra bonds to satisfy S.
7. Place remaining electrons, in (lone) pairs to
complete the octets for each atom.

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Lewis Structures
Example C2N2
Carbon has 4 valence electrons, nitrogen 5. A=18
Each atom wants an octet, N=32
Shared electrons S= 32-18 =14 (7 bonds)
Skeleton: (Electronegativities C 2.5, N 3.0)
N-C-C-N : Still need 4 more bonds.
N C C N is the only way to add the 4
bonds without having more than 8 electrons
around a carbon.
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Lewis Structures
Example C2N2
This uses 14 of the 18 electrons, so there are only 4
left. The carbons have their octet, each nitrogen
is 2 short so we must have one lone pair on each
nitrogen.
N C C N

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Formal Charges
The method of obtaining the Lewis structures
does not keep track of where the electrons
came from.
Hence we can get multiple results. However in
some structures atoms are not contributing equal
numbers of electrons to the bonds. This is less
likely to result in a stable configuration.

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Formal Charges
E.g. ONCl
O N Cl

O N Cl

Cl and N donate one electron each

Cl donates 3 electrons to the bond
O and N donate 2 electrons each
O donates 0 electrons to the bond
This seems more reasonable.

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Formal Charges
The formal charge is the apparent charge on
an atom that comes from unequal sharing of
electrons.
It can be used to decide between possible
structures.

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Formal Charges
The formal charge is the apparent charge on an atom that
comes from unequal sharing of electrons.
It can be used to decide between possible structures.

The formal charge on an atom is:

FC = # of valence electrons in free atom
# of lone pair electrons on the atom
(# of bonding electrons)

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Formal Charges
Rules for the most plausible Lewis structure:
1. The most plausible is the one where no atoms
have a formal charge.
2. Where formal charges are required, they should
be as small as possible.
3. Negative formal charges should be on the most
electronegative atoms.
4. Same sign formal charges on adjacent atoms
are unlikely.
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Formal Charges
E.g. ONCl
O N Cl

Formal charges
FC(O) = 6 -4-2 = 0
FC(N) = 5-2-3 = 0
FC(Cl) = 7-6-1 = 0

O N Cl

Formal charges
FC(O) = 6 -6-1 = -1 wrong
FC(N) = 5-2-3 = 0
FC(Cl) = 7-4-2 = +1 (wrong)2
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Formal Charges
Example: HCN
H

Remembering that C has 4 valence electrons and N 5

FC(H) = 0
FC(H) = 0
FC(C) = 0
FC(C) = 1
FC(N) = 0
FC(N) = +1
HCN is most likely.
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Formal Charges
Formal charges allow us to follow electrons
in bonding.
They are not the actual charges on atoms
What is the charge on an atom?

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Charges on atoms
O

Oxidation numbers assume that the

bonds are 100% ionic

2-

O
S

ON(S) = +6, ON(O) = 2

Formal charges assume bonds are 100%

covalent
FC(S) = 0, FC(O) = 0.5

The real charge is somewhere between

and is determined by the polarity of the
bonds
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Lee Allens Method

The degree of polarity in a bond involving
atom A and B depends on the
electronegativity of A and B
EN(A)
polarity
EN(A) EN(B)

IF EN(A) = EN(B) then half the charge is

on atom A (the bond is covalent)
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Lee Allens Method

In a molecule the charge on A is
EN(A)
q A = G A -N A -
N AB
B A EN(A) EN(B)
GA group number (the number of electrons in the atom)
NA Number of lone pair electrons on A
NAB is the number of bonding electrons between A
and B
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Lee Allens Method

For a 100% covalent bond EN(A) =EN(B)
EN(A)
q A = G A -N A -
N AB
B A EN(A) EN(B)
becomes
1
q A = G A -N A - N AB
2

This is the calculation for formal charge

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Charges on atoms
O

Oxidation numbers assume that the

bonds are 100% ionic

2-

O
S

ON(S) = +6, ON(O) = 2

Formal charges assume bonds are 100%

covalent
FC(S) = 0, FC(O) = 0.5

Lee Allens method

(EN(S) = 2.5, EN(O) = 3.5)

qS = 1.0, qO = 0.75
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Resonance
Consider ozone O3

O O O

O O O

These are both reasonable Lewis structures

BUT experimental evidence shows the
bonds are the same length.

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Resonance
The real structure is a hybrid of these two

O O O

O O O

This is called resonance. The real structure is a

resonance hybrid of these two structures.
The real structure has bonds which are between
single and double bonds. So what is the bond
order of the oxygen-oxygen bond in ozone?
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Exceptions/Extensions
Odd electron species: eg NO (11 electrons)
Lewis structures dont do a good job in this
case.
In general you can produce a Lewis structure
without the last electron and this goes on the
atom to minimize the formal charge.

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Exceptions/Extensions
Incomplete octets.
Sometimes when you make a sensible structure you
dont have enough electrons.
BF3
F

B
F

All atoms have a zero formal charge

Boron only has 6 electrons
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Exceptions/Extensions
BF3
Boron has a formal charge
of -1 The double bonded
fluorine +1
The need to obtain an octet
overrides the rule for
minimal formal charge
AND the ve formal charge
being on the most
electronegative atom.
Note we also have
resonance structures.
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F
B

Chemical Bonding 45

Exceptions/Extensions
Expanded valence shells.
To explain the bonding it sometimes seems
necessary to have more than 8 electrons in the
valence shell. This can be done for third period
elements by invoking the d orbitals.

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Expanded Octet Example

Sulphate, SO42O
O

FC(-O) = -1
FC(S) = +2

Octets are complete, but the

2formal charges are horrible.
Sulphur is in the 3rd period
so d orbitals may be
available for expanding the
octet to reduce formal
charges.
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Expanded Octet Example (cont.)

2-

O
O

S
O

FC(S) = +1
O

FC( single bonded O) = -1

FC(double bonded O) = 0

The octet around the S has been expanded to hold 10.

On basis of formal charge this is better.
Would formal charges be further reduced by further
expansion?
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Chemical Bonding 48

Expanded Octet Example (cont.)

2-

O
O

S
O

FC(S) = 0
FC( single bonded O) = -1
FC(double bonded O) = 0
Since there are resonance
forms FC(O) = 0.5

Is this the best possible structure?

Yes because we cannot lower the formal charges
further.
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Shapes of Molecules
In this section we will use Lewis structures as an
introduction to the shapes of molecules.
The key concepts are:
Electron pairs repel each other.
Electron pairs assume orientations to minimize
repulsion

This is the Valence Shell Electron Pair Repulsion

Theory (VSEPR)
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VSEPR
Example: Methane CH4
H
H

The 4 bond pairs must orient themselves to

minimize their repulsion.
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VSEPR Methane
The minimum interaction occurs
when the electron pairs point towards
the vertices of a tetrahedron.
The carbon is in the centre and the
hydrogen are at the vertices. The
molecule is tetrahedral.

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VSEPR Ammonia
Example: Ammonia NH3

H N

H
The 4 electron pairs must still orient
themselves to minimize their repulsion.

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Chemical Bonding 53

VSEPR Ammonia
The minimum interaction still occurs
when the electron pairs point towards
the vertices of a tetrahedron.
The nitrogen is in the centre and the
hydrogens are at three of the vertices.
The lone pair points to the fourth.
The molecule is trigonal pyramidal.

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Chemical Bonding 54

VSEPR Water
Example: Water H2O

H
O H
The 4 electron pairs must orient themselves to
minimize their repulsion.
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Chemical Bonding 55

VSEPR Water
The minimum interaction still occurs
when the electron pairs point towards
the vertices of a tetrahedron.
The oxygen is in the centre, the
hydrogens are at two of the vertices.
The lone pairs point to the other two.
The molecule is bent.

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Chemical Bonding 56

Bond Angles
This analysis suggests that all three molecules
should have bond angles of 109.5o.
The methane bond angle is 109.5o but for ammonia
it is 107o and in water it is 104.5o
The lone pair electrons are not constrained as much
as the bonding pairs. They spread out thus the
repulsive forces are:
Lone pair-lone pair>Lone pair-bond pair>bond pair-bond pair

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Molecular Geometry
VSEPR theory can be used to describe the
shapes of most molecules.
Warnings
When you describe the shape, dont include the
lone pairs. (water is bent, not tetrahedral)
Molecules have three dimensions (methane is a
tetrahedron not a square)

Be familiar with table 10.1 pg 399-400

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Going Beyond Lewis Structures

Lewis structures are very useful in
explaining the bonding in simple molecules
and in predicting molecular shapes.
They do not explain why electrons in bond
pairs bring nuclei together.
They can not be used to estimate bond
lengths or bond strengths.
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Chemical Bonding 65

Going Beyond Lewis Structures

There are two currently used bonding theories,
valence bond theory and molecular orbital theory.
Valence bond theory envisions bonding as
resulting from the overlap of atomic orbitals.
Molecular orbital theory moves past atomic
orbitals and derives orbitals that belong to the
molecule as a whole.
We will concentrate on valence bond theory as
that is sufficient to rationalize the structures we
see.
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Chemical Bonding 66

Valence Bond Method

This method considers what happens to the
valence orbitals (the outer shell).
If the atoms start a long way apart, there is no
interaction.
As the atoms move closer together the orbitals
may overlap.
If there is an electron in the orbital then there is a
high probability of finding an electron between the
nuclei.
This is the region where there is a covalent bond.
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Valence Bond Method

We cannot ignore the previously developed
rules, so there are only two electrons per
bond
Overlap can only occur for 2 half filled orbitals
or one empty and one filled orbital.

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Chemical Bonding 68

Valence Bond Method

H 2S

Not shown

This suggests the bond angle should be 90o.

It is 92o.
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Chemical Bonding 69

Valence Bond method for methane

Chemically methane is stable
We know from VSEPR that methane is
tetrahedral
BUT

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Chemical Bonding 70

Valence Bond method for methane

The valence bond theory (so far) would
suggest that the 1s electrons from H will be
donated to the p orbitals to pair-up the
unpaired electrons.
In this case we would have CH2
Thats not what is seen. We need CH4.

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Chemical Bonding 71

Valence Bond method for methane

Somehow the carbon needs to have 4
unpaired electrons
This gives 4 unpaired electrons

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Chemical Bonding 72

Valence Bond method for methane

This costs energy, as it makes an excited
state C atom.
Also if we try to use these orbitals in
bonding, the orientation is wrong.
If hydrogens attached to the p orbitals, they
would be orthogonal.
Where would the overlap with the s be?
We know the molecule is tetrahedral.
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Chemical Bonding 73

Valence Bond Rethinking

We can no longer assume that the orbitals in a
bonded atom are the same as those of an isolated
atom.
Remember that the atomic orbitals come from
solving an equation assuming a single nucleus. In
a molecule the electron has to respond to more
nuclei.
We should solve the new problem, but we
usually say we can combine the atomic orbitals in
some way.
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Chemical Bonding 74

Valence Bond method for methane

Since the orbitals are wave functions, we can take
the 2s and 2p wave functions and combine them to
give 4 equivalent wave functions. These can be
made to have the same shape and energy.
This is called hybridization and the resulting
orbitals are called hydrid orbitals.
The combination of one s and three p orbitals
gives four sp3 hybrid orbitals.

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Generation of sp3
hybrid orbitals

Same shape but

different orientation to
minimize interaction

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Chemical Bonding 76

Methane

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Chemical Bonding 77

Energy and Hybrid Orbitals

What about the energy?
The energy of the orbitals is conserved because
the sp3 orbitals have an energy between the s and p
orbitals.

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Chemical Bonding 78

Energy and Hybrid Orbitals

However there will be an energy cost in making the
sp hybrids with one electron in each.
The orbitals are generated assuming only one electron

So why would the molecule do something that will

cost energy?
Once the molecule is formed you release the bond
energy. If this is greater than the cost then it is
worthwhile.

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Chemical Bonding 79

Ammonia

Now we have a pair of electrons in one of

the sp3 hybrid orbitals, so it cant bond with
hydrogen.
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Chemical Bonding 80

Ammonia

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NH3 versus PH3

NH3 has sp3 bonding and a bond angle of
~109.
PH3 has a bond angle of 93 so it looks like it
does not hybridize.
It still hybridizes but the angle is 93
The lone pair on the P is larger than that on the N
Thus the bond pair-bond pair angle is even
smaller in PH3
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 The sp3 hybrid orbitals dont explain the

bonding for Boron (group 13) or for
Beryllium (group 2)

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Chemical Bonding 83

 The problem appears to be that there are

insufficient electrons to even half fill the 4
sp3 orbitals.
In these case we need to consider different
hybridization schemes.
We define hybrids such that the number of
hybrids is the same as the number of
valence electrons.
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Chemical Bonding 84

sp2 and sp hybrid orbitals

Boron
The number of orbitals is
conserved.

Beryllium

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Chemical Bonding 85

sp2 hybrid orbitals (BCl3)

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Chemical Bonding 86

sp hybrid orbitals (BeCl2)

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Multiple bonds
How do we deal with the Lewis structures
that have multiple bonds?
Consider ethylene C2H4
H

H
C

H
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Multiple bonds: ethylene (C2H4)

The geometry suggests sp2 hybrid orbitals
are involved.

There is still an electron in the remaining 2p orbital.

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Multiple bonds: ethylene (C2H4)

The sp2 hybrid
orbitals are in
purple.
The p
orbital is
blue/red

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Chemical Bonding 90

Multiple bonds: ethylene (C2H4)

The orbitals that overlap along the axis of the
nuclei are called sigma bonds - bonds.
Those where the overlap is side-to-side are pi
bonds - bonds.

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Multiple bonds: ethylene

The bonds determine the shape of the molecule,
the bonds restrict the rotation about the C-C
axis.
The orbital overlap is more extensive for the bonds
so the bond is weaker than the bond.
Bond strengths
C-C 347 kJ mol-1
C=C 611 kJ mol-1
difference = 264 kJ mol-1
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Multiple bonds: acetylene (ethyne)

H

The geometry suggests sp hybrid orbitals

are involved.

There is still an electron in each of the

remaining 2p orbitals.
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Multiple bonds: acetylene (ethyne)

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Multiple bonds: d orbitals

2-

In sulphate we needed pi
bonding and to use the d
orbitals on the sulphur.
Without worrying about
resonance structures, can we
explain the bonding?

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Multiple bonds: d orbitals sulphate

2-

O
O

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Multiple bonds: d orbitals sulphate

2-

O
O

8 electrons
6 orbitals

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Multiple bonds: d orbitals sulphate

2-

O
O

8 electrons
6 orbitals

Why 6 orbitals?
For the resonant structures
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Delocalization
This is an alternative method of describing
molecules that have resonant structures.
Eg Ozone
O O O

O O O

We can describe the pi bonding as being

delocalised
The pi electrons are delocalised among 3 atoms
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Delocalization
Eg Ozone
O O O

O O O

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Multiple Bonds: Benzene

This structure is planar and suggests sp2.

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Multiple Bonds: Benzene

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Multiple Bonds: Benzene

In this case the 6 pi electrons are
delocalized over all 6 atoms of the
molecule.

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