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FORMAL CHARGES

Resonance Hybrids & Formal charges

Outcomes
Represent all possible resonance hybrids
Allocate formal charges
Determine the most stable resonance structure using formal charges

Formal charges (FC)

Formal charges help to weight different resonance structures

(Which one of them is more important than others?).

They also help to predict the reactivity of molecules. This is of

particular importance in organic chemistry: many mechanisms
involve intermediates which carry formal charges.

Formal charges - continued

To allocate formal charges to an atom in a Lewis electron-dot structure

(LEDS) of a molecule:

compare the number of valence electrons in the free atom with the
number of valence electrons (lone pairs) in the bonded atom.

For each bond, the bonding electrons are divided between the two
atoms which are connected.

The non-bonding electrons (lone pairs) remain the sole property of

the atom which carries them:

FC (X) = No. of valence electrons in a free atom - (1/2 bonding electrons + non-bonding
electrons)

Faculty/Department name here 18pt Arial

Formal charges - continued

Formal charge calculations are used as a guideline to the correct

structure.

A zero formal charge is usually a good indication of a stable

structure.

The sum of formal charges in a neutral molecule is zero e.g.

CH3CONH2.

The sum of formal charges in an ion equals the charge of the ion,
e.g. NH4+.

Formal charges - continued

There are two rules used to determine the most likely Lewis
structure(s).
Atoms try to achieve formal charges as close to zero as
possible.
Any negative formal charges should reside on the most
electronegative atoms.

Formal charges - continued

Exercise

Consider the ion SCN-1 and draw all valid Lewis dot structures for
the ion.

Use formal charges to determine the major contributor(s) to the

actual structure of the ion.

http://2012books.lardbucket.org/books/principles-of-general-chemistry-v1.0/s12-05-lewisstructures-and-covalent-.html

Exercise - continued
Draw Lewis structures for the BeF2 molecule in which (a) the BeF2
molecule has two single bonds and (b) the BeF2 molecule has two
double bonds.
Which of the two structures satisfies the octet rule for both Be and
F?
Calculate formal charge values for atoms in both the single bonded
and double bonded structure. Do formal charge values favour one
structure over the other?

Exceptions to the Octet Rule

Molecules with odd no. of electrons, e.g. ClO2, NO, NO2 and O2-.

Molecules with less than an Octet of valence electrons, e.g. BF3.

More than an Octet of valence electrons, e.g. PF5.

Challenging problem

Determine the most dominant Lewis structure of phosphate ion

(PO43-) and explain why?

END OF LECTURE