Million 1

Logan Million

Vincent Blazis

Chemistry 121

24 April 2015

Tyrosine

Introduction

Tyrosine, also known as 4-hydroxyphenylalanine, is an amino acid that is

responsible for the production of proteins.

Lewis Structures and Bond Angles

Lewis structures are a way of diagraming different atoms and ions in molecules,

along with their respective electrons. They allow one to predict the behavior of molecular

as they show where and how many bonds an atom will have. Each atom will have bonds

that influence the overall shape and behavior of the molecule. The Lewis Structure and

bond angles for D-Tyrosine are as follows:

 Million 2

The next descriptions will be from left to right looking at the molecule. The

hydrogen on the left side is bonded to the oxygen, and since hydrogen only has one

electron to bond with oxygen, it has no free electrons. The first oxygen on the left has a

bond to both hydrogen and carbon, and since it has six valence electrons total that leaves

four electrons (or two electron groups) free on the atom. This creates a molecular shape

of “bent” with a bond angle of approximately 109.5°.

- All of the carbons on the benzene ring have the same Lewis Diagrams as they all

are fully bonded with four bonds (three going to other carbons and one going to a

hydrogen) and produce trigonal planar molecular shapes (each with an approximate angle

of 120°). The exceptions are the 1-carbon and the 4-carbon as they are bonded with an

oxygen and two carbons and three carbons respectively (these also have a bond angle of

120° as trigonal planar).

- The carbon to the right of the benzene ring is fully bonded with two hydrogen

atoms and two carbon atoms, which leaves no free electrons in space. As it is connected

with four different groups without any lone electrons, this carbon forms a tetrahedral

group with bond angles of 109.5°.

- The next carbon over to the right is also fully bonded with two going towards

carbon atoms, one going to nitrogen in the amine group, and another going to a lone

hydrogen atom. This carbon also forms a tetrahedral group with bond angles of 109.5°.

- In the amine group, nitrogen has one electron going to carbon and two going to

the hydrogen atoms. This leaves two free electrons in space. A trigonal pyramidal group

is formed with bond angles of approximately 109.5°.

 Million 3

- On the other side of the molecule, the carbon that helps form the carboxylic acid

group has a double bond with the lone oxygen, a group shared with its neighboring

carbon, and one group shared with the oxygen in the OH group. This gives it a trigonal

planar group with bond angles of 120°.

- The oxygen in the OH group has one bond with carbon, and another with hydrogen.

This leaves four unpaired electrons, which leads to a bent molecular shape, and bond

angles of 109.5°.

- The single oxygen is only attached to the carbon on the far right side by a double

bond, leaving four unpaired electrons. This forms a linear molecular geometry, but

trigonal planar electron geometry. These have bond angles of 120°.

Bond Types

In Tyrosine, there are only two kinds of bonds present: single and double bonds.

The double bonds are found in the Benzene ring (where there are three at any point) and

between the carbon and lone oxygen in the carboxylic acid group. All other bonds in

Tyrosine are single bonds.

All of the single bonds in Tyrosine are sigma bonds, which extend between in a

straight line between the two atoms. For example, here is a diagram of the first sigma

bond from the left, between oxygen and hydrogen.

 Million 4

All of the double bonds in Tyrosine consist of one sigma and one pi bond. The

sigma goes through the middle, while the pi bond reaches over the top and bottom of the

sigma bond. For example, here is a diagram of the bond between the lone oxygen and its

carbon atom:

Chirality

Like most amino acids, Tyrosine is a chiral molecule. It has no real axis of

symmetry, so that is one indicator of its chirality. It has a chiral center at the carbon

attached to the carboxyl group, and this is a trend for most amino acids. The chiral center

is where a molecule can be flipped from to make its counterpart. For example, this is

what L-Tyrosine looks like:

 Million 5

And here is R-Tyrosine:

From these diagrams it is easy to see where the chiral center is located.

Resonance

There are two main areas of resonance in Tyrosine: the benzene ring and the

carboxylic acid group. The benzene ring has three single and three double bonds, which

are spaced out one after the other. Since these structures are constantly in motion, we

draw it as such:

This representation helps reinforce the idea that all of the possibilities occur

almost simultaneously. The other resonance structure, in the carboxyl group, switches

between the lone oxygen and the hydroxyl alcohol group. The double bond from the

carbon resonates from each oxygen to the other.

 Million 6

Polarity

Tyrosine has various points of polarity, due to the fact that there are no

symmetrical pulls on either “side”. If we look at Tyrosine:

We can see that there are at least four different end groups on the molecule, each with

their own unique electronegative pulls. Since each functional group is comprised of

different atoms, each will have their own electronegative totals For example, a hydroxyl

group is going to be different from the amine group down the carbon line.

Bond Order:

The bond orders for each atom in Tyrosine (drawn below) are as follows:
 Million 7

Word Count: 963