Introduction to Conjugation

So what is Conjugation and what does it do?

To begin, conjugation is when there are three or more parallel, adjacent overlapping p-orbitals
which results in electron delocalization and longer wavelengths. This creates stability for the
molecule and more space for electrons to run around in.
Example:

See how there is

electron delocalization!

1, 3- pentene: This molecule is conjugated because it has more

than three overlapping p-orbitals and they are adjacent to
each other.
Compared to . . .
This molecule is not conjugated. It
does not have three adjacent,
parallel, overlapping p-orbitals.
Does conjugation increase stability?
Yes, resonance allows pi electrons to be delocalized over more atoms.
Barrier to rotation, what is it?
It is the difference in energy between the most stable and least stable conformations when
considering rotation around a bond. A bond with partial pi character has a higher barrier to
rotation than a similar bond without partial pi character.
Why are conjugated molecules planar?
The reason is because planarity gives maximal p-orbital overlap and has the lowest energy by
minimizing electron repulsion.
A tetrahedral shape is more stable than a square planar
Staggered conformation is more stable than eclipsed
What if a molecule is in a ring, can it be conjugated?
Yes. As long as there is no ring strain and there are at least three adjacent parallel overlapping
p-orbitals.
Ex.

:O:

Both of these molecule have 6 overlapping

p-orbitals, so they are both conjugated!

What happens if a molecule has many conjugated atoms?

Molecules that are significantly conjugated can be colored
How?
The molecule absorbs a photon and an electron gets excited and moves up to a higher molecular
orbital. It has to do with the HOMO-LUMO gap.

If a Violet photon is absorbed, then you observe the color Yellow

If an Indigo photon is absorbed, then you observe the color Orange
If a Blue photon is absorbed then, you observe the color Red
If a Green photon is absorbed, then you observe the color Violet
If a Yellow photon is absorbed, then you observe the color Indigo
If an Orange photon is absorbed, then you observe the color Blue
If a Red photon is absorbed, then you observe the color Green
If a photon of UV light is absorbed, then you observe a colorless color

Practice P roblems
Are the following molecules conjugated??

O
a)

c)

NH2
NH2
b)

d)

e)

f)
Cl

g) What criteria does a molecule have to

follow in order for it to be conjugated?

h) If you observe the color Red, what photon is

being absorbed?

Practice Problem Solutions

a) Yes, it is conjugated
b) Yes, it is conjugated
c) Not conjugated
d) Yes, it is conjugated
e) Not conjugated
f) Not conjugated
g) There has to be 3 or more parallel, adjacent and overlapping p-orbitals
h) Blue photon

Sources:
Organic Chemistry at UCLA. Illustrated Glossary.
Chemistry 14C Lecture Supplement/Thinkbook