Professional Documents
Culture Documents
Each atom in a
bond has a partial
charge of about
+0.5 or 0.5 units
when the
electronegativity
difference is 1.7.
:O: :O:
| ||
HO
S O
H HO
S O
H
| ||
:O
: :O:
Structure I Structure II
Structure I obeys the octet rule, but is not
consistent with experiment
Structure II violates the octet rule, but is
consistent with experiment
Structure II is the preferred Lewis structure
Formal charge is the apparent charge on an
atom
The formal charge on a atom is calculated
by subtracting the number of valence
electrons assigned to it in a Lewis structure
from the number of valence electrons in an
isolated atom
formal valence e on number of bonds number of
charge
isolated atom to the atom unshared e
Consider the sulfur atoms in the two
structures for sulfuric acid:
Structure I: formal charge on S = 6 - (4 + 0) = +2
Structure II: formal charge on S = 6 - (6 + 0) = 0
When several Lewis structures are possible,
those with the smallest formal charges are
the most stable and preferred
Note that the formal charges for all atoms in
a Lewis structure sum to the charge on the
species
Some molecules and ions are not well
represented by a single Lewis structure
Consider the case of the formate ion
Experiment gives a single carbon-oxygen
bond length
A combination of structures is needed to
describe this ion
These are called resonance structures and
the ion is said to be a resonance hybrid of
the contributing structures
:O :
:O :
H C O : H C O :
|| |
Two resonance structures are required for
the formate ion because two equivalent
carbon-oxygen double bonds can be formed
Note that three resonance structures would
be required to represent SO3
The total energy of a resonance hybrid is
lower in energy than any one of its
resonance structures
This energy lowering is called the
resonance energy
Benzene has a planar
hexagonal structure and is
a resonance hybrid of
resonance structures. Its
resonance energy is about
146 kJ/mol.
Consider the formation of the ammonium
ion from ammonia and a hydrogen ion in
solution
H H
|
|
H N : H H N H
| |
H H
The nitrogen donates both of the electrons
when forming the bond to H+
This is called a coordinate covalent bond
The concept of a coordinate bond can be
useful when trying to understand what
happens to atoms in reactions
For example, addition compounds involve
coordinate covalent bonds and can result
when two small molecules join
H :Cl: H :Cl:
| | | |
H N : B Cl
: H N B Cl
:
| | | |
H :Cl:
H :Cl: